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Stereoretentive palladium-catalyzed arylation, alkenylation, and alkynylation of 1-thiosugars and thiols using aminobiphenyl palladacycle precatalyst at room temperature.

Chemistry (Weinheim an der Bergstrasse, Germany)

Bruneau A, Roche M, Hamze A, Brion JD, Alami M, Messaoudi S.
PMID: 25876554
Chemistry. 2015 Jun 01;21(23):8375-9. doi: 10.1002/chem.201501050. Epub 2015 Apr 15.

A general and efficient protocol for the palladium-catalyzed functionalization of mono- and polyglycosyl thiols by using the palladacycle precatalyst G3-XantPhos was developed. The C-S bond-forming reaction was achieved rapidly at room temperature with various functionalized (hetero)aryl-, alkenyl-, and alkynyl...

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Bruneau A, Roche M, Hamze A, et al. Stereoretentive palladium-catalyzed arylation, alkenylation, and alkynylation of 1-thiosugars and thiols using aminobiphenyl palladacycle precatalyst at room temperature. Chemistry. 2015;21(23):8375-9doi: 10.1002/chem.201501050.
Bruneau, A., Roche, M., Hamze, A., Brion, J. D., Alami, M., & Messaoudi, S. (2015). Stereoretentive palladium-catalyzed arylation, alkenylation, and alkynylation of 1-thiosugars and thiols using aminobiphenyl palladacycle precatalyst at room temperature. Chemistry (Weinheim an der Bergstrasse, Germany), 21(23), 8375-9. https://doi.org/10.1002/chem.201501050
Bruneau, Alexandre, et al. "Stereoretentive palladium-catalyzed arylation, alkenylation, and alkynylation of 1-thiosugars and thiols using aminobiphenyl palladacycle precatalyst at room temperature." Chemistry (Weinheim an der Bergstrasse, Germany) vol. 21,23 (2015): 8375-9. doi: https://doi.org/10.1002/chem.201501050
Bruneau A, Roche M, Hamze A, Brion JD, Alami M, Messaoudi S. Stereoretentive palladium-catalyzed arylation, alkenylation, and alkynylation of 1-thiosugars and thiols using aminobiphenyl palladacycle precatalyst at room temperature. Chemistry. 2015 Jun 01;21(23):8375-9. doi: 10.1002/chem.201501050. Epub 2015 Apr 15. PMID: 25876554.
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Appel-reagent-mediated transformation of glycosyl hemiacetal derivatives into thioglycosides and glycosyl thiols.

Beilstein journal of organic chemistry

Ghosh T, Santra A, Misra AK.
PMID: 23766814
Beilstein J Org Chem. 2013 May 22;9:974-982. doi: 10.3762/bjoc.9.112. Print 2013.

A series of glycosyl hemiacetal derivatives have been transformed into thioglycosides and glycosyl thiols in a one-pot two-step reaction sequence mediated by Appel reagent (carbon tetrabromide and triphenylphosphine). 1,2-trans-Thioglycosides and β-glycosyl thiol derivatives were stereoselectively formed by the reaction...

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Ghosh T, Santra A, Misra AK. Appel-reagent-mediated transformation of glycosyl hemiacetal derivatives into thioglycosides and glycosyl thiols. Beilstein J Org Chem. 2013;9:974-982doi: 10.3762/bjoc.9.112.
Ghosh, T., Santra, A., & Misra, A. K. (2013). Appel-reagent-mediated transformation of glycosyl hemiacetal derivatives into thioglycosides and glycosyl thiols. Beilstein journal of organic chemistry, 9974-982. https://doi.org/10.3762/bjoc.9.112
Ghosh, Tamashree, et al. "Appel-reagent-mediated transformation of glycosyl hemiacetal derivatives into thioglycosides and glycosyl thiols." Beilstein journal of organic chemistry vol. 9 (2013): 974-982. doi: https://doi.org/10.3762/bjoc.9.112
Ghosh T, Santra A, Misra AK. Appel-reagent-mediated transformation of glycosyl hemiacetal derivatives into thioglycosides and glycosyl thiols. Beilstein J Org Chem. 2013 May 22;9:974-982. doi: 10.3762/bjoc.9.112. Print 2013. PMID: 23766814; PMCID: PMC3678522.
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Chemoselective Glycosylations. 2. Differences in Size of Anomeric Leaving Groups Can Be Exploited in Chemoselective Glycosylations.

The Journal of organic chemistry

Geurtsen R, Holmes DS, Boons GJ.
PMID: 11671924
J Org Chem. 1997 Nov 14;62(23):8145-8154. doi: 10.1021/jo971233k.

We have developed a novel chemoselective glycosylation strategy. This glycosylation strategy is based on the fact that the glycosyl reactivity of an anomeric thiol group can be controlled by the bulkiness of this group whereby we have produced a...

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Geurtsen R, Holmes DS, Boons GJ. Chemoselective Glycosylations. 2. Differences in Size of Anomeric Leaving Groups Can Be Exploited in Chemoselective Glycosylations. J Org Chem. 1997;62(23):8145-8154doi: 10.1021/jo971233k.
Geurtsen, R., Holmes, D. S., & Boons, G. J. (1997). Chemoselective Glycosylations. 2. Differences in Size of Anomeric Leaving Groups Can Be Exploited in Chemoselective Glycosylations. The Journal of organic chemistry, 62(23), 8145-8154. https://doi.org/10.1021/jo971233k
Geurtsen, Richard, et al. "Chemoselective Glycosylations. 2. Differences in Size of Anomeric Leaving Groups Can Be Exploited in Chemoselective Glycosylations." The Journal of organic chemistry vol. 62,23 (1997): 8145-8154. doi: https://doi.org/10.1021/jo971233k
Geurtsen R, Holmes DS, Boons GJ. Chemoselective Glycosylations. 2. Differences in Size of Anomeric Leaving Groups Can Be Exploited in Chemoselective Glycosylations. J Org Chem. 1997 Nov 14;62(23):8145-8154. doi: 10.1021/jo971233k. PMID: 11671924.
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Stereospecific synthesis of 1,2-cis glycosides by vinyl-mediated IAD.

Organic letters

Chayajarus K, Chambers DJ, Chughtai MJ, Fairbanks AJ.
PMID: 15469352
Org Lett. 2004 Oct 14;6(21):3797-800. doi: 10.1021/ol048427o.

[reaction: see text] Stereospecific 1,2-cis glycosylation of 2-O-vinyl thioglycosides, synthesized from the corresponding alcohols by Ir-catalyzed transvinylation with vinyl acetate, is achieved by iodine-mediated tethering of a range of primary and secondary carbohydrate acceptors, followed by intramolecular aglycon delivery...

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Chayajarus K, Chambers DJ, Chughtai MJ, et al. Stereospecific synthesis of 1,2-cis glycosides by vinyl-mediated IAD. Org Lett. 2004;6(21):3797-800doi: 10.1021/ol048427o.
Chayajarus, K., Chambers, D. J., Chughtai, M. J., & Fairbanks, A. J. (2004). Stereospecific synthesis of 1,2-cis glycosides by vinyl-mediated IAD. Organic letters, 6(21), 3797-800. https://doi.org/10.1021/ol048427o
Chayajarus, Kampanart, et al. "Stereospecific synthesis of 1,2-cis glycosides by vinyl-mediated IAD." Organic letters vol. 6,21 (2004): 3797-800. doi: https://doi.org/10.1021/ol048427o
Chayajarus K, Chambers DJ, Chughtai MJ, Fairbanks AJ. Stereospecific synthesis of 1,2-cis glycosides by vinyl-mediated IAD. Org Lett. 2004 Oct 14;6(21):3797-800. doi: 10.1021/ol048427o. PMID: 15469352.
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Stereoselective synthesis of 2-deoxy-furanosides from 2,3-anhydro-furanosyl thioglycosides.

Organic letters

Hou D, Lowary TL.
PMID: 17915885
Org Lett. 2007 Oct 25;9(22):4487-90. doi: 10.1021/ol7019108. Epub 2007 Oct 04.

The stereocontrolled synthesis of 2-thiotolyl-furanosides from 2,3-anhydro-furanosyl thioglycosides through a rearrangement-glycosylation process is reported. The efficiency of this reaction is high, providing 70-95% yields of the products. Treatment of the resulting 2-deoxy-2-thiotolyl-glycosides with hydrogen and Raney nickel affords the...

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Hou D, Lowary TL. Stereoselective synthesis of 2-deoxy-furanosides from 2,3-anhydro-furanosyl thioglycosides. Org Lett. 2007;9(22):4487-90doi: 10.1021/ol7019108.
Hou, D., & Lowary, T. L. (2007). Stereoselective synthesis of 2-deoxy-furanosides from 2,3-anhydro-furanosyl thioglycosides. Organic letters, 9(22), 4487-90. https://doi.org/10.1021/ol7019108
Hou, Dianjie, and Lowary, Todd L. "Stereoselective synthesis of 2-deoxy-furanosides from 2,3-anhydro-furanosyl thioglycosides." Organic letters vol. 9,22 (2007): 4487-90. doi: https://doi.org/10.1021/ol7019108
Hou D, Lowary TL. Stereoselective synthesis of 2-deoxy-furanosides from 2,3-anhydro-furanosyl thioglycosides. Org Lett. 2007 Oct 25;9(22):4487-90. doi: 10.1021/ol7019108. Epub 2007 Oct 04. PMID: 17915885.
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Synthesis of homo- and heteromultivalent carbohydrate-functionalized oligo(amidoamines) using novel glyco-building blocks.

Beilstein journal of organic chemistry

Wojcik F, Lel S, O'Brien AG, Seeberger PH, Hartmann L.
PMID: 24367405
Beilstein J Org Chem. 2013 Nov 07;9:2395-403. doi: 10.3762/bjoc.9.276. eCollection 2013.

We present the solid phase synthesis of carbohydrate-functionalized oligo(amidoamines) with different functionalization patterns utilizing a novel alphabet of six differently glycosylated building blocks. Highly efficient in flow conjugation of thioglycosides to a double-bond presenting diethylentriamine precursor is the key...

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Wojcik F, Lel S, O'Brien AG, et al. Synthesis of homo- and heteromultivalent carbohydrate-functionalized oligo(amidoamines) using novel glyco-building blocks. Beilstein J Org Chem. 2013;9:2395-403doi: 10.3762/bjoc.9.276.
Wojcik, F., Lel, S., O'Brien, A. G., Seeberger, P. H., & Hartmann, L. (2013). Synthesis of homo- and heteromultivalent carbohydrate-functionalized oligo(amidoamines) using novel glyco-building blocks. Beilstein journal of organic chemistry, 92395-403. https://doi.org/10.3762/bjoc.9.276
Wojcik, Felix, et al. "Synthesis of homo- and heteromultivalent carbohydrate-functionalized oligo(amidoamines) using novel glyco-building blocks." Beilstein journal of organic chemistry vol. 9 (2013): 2395-403. doi: https://doi.org/10.3762/bjoc.9.276
Wojcik F, Lel S, O'Brien AG, Seeberger PH, Hartmann L. Synthesis of homo- and heteromultivalent carbohydrate-functionalized oligo(amidoamines) using novel glyco-building blocks. Beilstein J Org Chem. 2013 Nov 07;9:2395-403. doi: 10.3762/bjoc.9.276. eCollection 2013. PMID: 24367405; PMCID: PMC3869284.
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Carbohydrates as Multifunctional Chiral Scaffolds in Combinatorial Synthesis.

Angewandte Chemie (International ed. in English)

Wunberg T, Kallus C, Opatz T, Henke S, Schmidt W, Kunz H.
PMID: 29711363
Angew Chem Int Ed Engl. 1998 Oct 02;37(18):2503-2505. doi: 10.1002/(SICI)1521-3773(19981002)37:18<2503::AID-ANIE2503>3.0.CO;2-R.

Four orthogonally stable protecting groups and a selectively cleavable anchor that are stable under basic conditions are required in order that carbohydrates can be employed as chiral polyfunctional scaffolds in combinatorial solid-phase syntheses of high diversity. The schematic representation...

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Wunberg T, Kallus C, Opatz T, et al. Carbohydrates as Multifunctional Chiral Scaffolds in Combinatorial Synthesis. Angew Chem Int Ed Engl. 1998;37(18):2503-2505doi: 10.1002/(SICI)1521-3773(19981002)37:18<2503::AID-ANIE2503>3.0.CO;2-R.
Wunberg, T., Kallus, C., Opatz, T., Henke, S., Schmidt, W., & Kunz, H. (1998). Carbohydrates as Multifunctional Chiral Scaffolds in Combinatorial Synthesis. Angewandte Chemie (International ed. in English), 37(18), 2503-2505. https://doi.org/10.1002/(SICI)1521-3773(19981002)37:18<2503::AID-ANIE2503>3.0.CO;2-R
Wunberg, Tobias, et al. "Carbohydrates as Multifunctional Chiral Scaffolds in Combinatorial Synthesis." Angewandte Chemie (International ed. in English) vol. 37,18 (1998): 2503-2505. doi: https://doi.org/10.1002/(SICI)1521-3773(19981002)37:18<2503::AID-ANIE2503>3.0.CO;2-R
Wunberg T, Kallus C, Opatz T, Henke S, Schmidt W, Kunz H. Carbohydrates as Multifunctional Chiral Scaffolds in Combinatorial Synthesis. Angew Chem Int Ed Engl. 1998 Oct 02;37(18):2503-2505. doi: 10.1002/(SICI)1521-3773(19981002)37:18<2503::AID-ANIE2503>3.0.CO;2-R. PMID: 29711363.
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Urea-hydrogen peroxide prompted the selective and controlled oxidation of thioglycosides into sulfoxides and sulfones.

Beilstein journal of organic chemistry

Singh AK, Tiwari V, Mishra KB, Gupta S, Kandasamy J.
PMID: 28684993
Beilstein J Org Chem. 2017 Jun 13;13:1139-1144. doi: 10.3762/bjoc.13.113. eCollection 2017.

A practical method for the selective and controlled oxidation of thioglycosides to corresponding glycosyl sulfoxides and sulfones is reported using urea-hydrogen peroxide (UHP). A wide range of glycosyl sulfoxides are selectively achieved using 1.5 equiv of UHP at 60...

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Singh AK, Tiwari V, Mishra KB, et al. Urea-hydrogen peroxide prompted the selective and controlled oxidation of thioglycosides into sulfoxides and sulfones. Beilstein J Org Chem. 2017;13:1139-1144doi: 10.3762/bjoc.13.113.
Singh, A. K., Tiwari, V., Mishra, K. B., Gupta, S., & Kandasamy, J. (2017). Urea-hydrogen peroxide prompted the selective and controlled oxidation of thioglycosides into sulfoxides and sulfones. Beilstein journal of organic chemistry, 131139-1144. https://doi.org/10.3762/bjoc.13.113
Singh, Adesh Kumar, et al. "Urea-hydrogen peroxide prompted the selective and controlled oxidation of thioglycosides into sulfoxides and sulfones." Beilstein journal of organic chemistry vol. 13 (2017): 1139-1144. doi: https://doi.org/10.3762/bjoc.13.113
Singh AK, Tiwari V, Mishra KB, Gupta S, Kandasamy J. Urea-hydrogen peroxide prompted the selective and controlled oxidation of thioglycosides into sulfoxides and sulfones. Beilstein J Org Chem. 2017 Jun 13;13:1139-1144. doi: 10.3762/bjoc.13.113. eCollection 2017. PMID: 28684993; PMCID: PMC5480342.
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Establishment of Guidelines for the Control of Glycosylation Reactions and Intermediates by Quantitative Assessment of Reactivity.

Angewandte Chemie (International ed. in English)

Chang CW, Wu CH, Lin MH, Liao PH, Chang CC, Chuang HH, Lin SC, Lam S, Verma VP, Hsu CP, Wang CC.
PMID: 31518045
Angew Chem Int Ed Engl. 2019 Nov 18;58(47):16775-16779. doi: 10.1002/anie.201906297. Epub 2019 Oct 11.

Stereocontrolled chemical glycosylation remains a major challenge despite vast efforts reported over many decades and so far still mainly relies on trial and error. Now it is shown that the relative reactivity value (RRV) of thioglycosides is an indicator...

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Chang CW, Wu CH, Lin MH, et al. Establishment of Guidelines for the Control of Glycosylation Reactions and Intermediates by Quantitative Assessment of Reactivity. Angew Chem Int Ed Engl. 2019;58(47):16775-16779doi: 10.1002/anie.201906297.
Chang, C. W., Wu, C. H., Lin, M. H., Liao, P. H., Chang, C. C., Chuang, H. H., Lin, S. C., Lam, S., Verma, V. P., Hsu, C. P., & Wang, C. C. (2019). Establishment of Guidelines for the Control of Glycosylation Reactions and Intermediates by Quantitative Assessment of Reactivity. Angewandte Chemie (International ed. in English), 58(47), 16775-16779. https://doi.org/10.1002/anie.201906297
Chang, Chun-Wei, et al. "Establishment of Guidelines for the Control of Glycosylation Reactions and Intermediates by Quantitative Assessment of Reactivity." Angewandte Chemie (International ed. in English) vol. 58,47 (2019): 16775-16779. doi: https://doi.org/10.1002/anie.201906297
Chang CW, Wu CH, Lin MH, Liao PH, Chang CC, Chuang HH, Lin SC, Lam S, Verma VP, Hsu CP, Wang CC. Establishment of Guidelines for the Control of Glycosylation Reactions and Intermediates by Quantitative Assessment of Reactivity. Angew Chem Int Ed Engl. 2019 Nov 18;58(47):16775-16779. doi: 10.1002/anie.201906297. Epub 2019 Oct 11. PMID: 31518045.
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Solid-Phase Synthesis of Oligosaccharides: Construction of a Dodecasaccharide.

Angewandte Chemie (International ed. in English)

Nicolaou KC, Watanabe N, Li J, Pastor J, Winssinger N.
PMID: 29710918
Angew Chem Int Ed Engl. 1998 Jun 19;37(11):1559-1561. doi: 10.1002/(SICI)1521-3773(19980619)37:11<1559::AID-ANIE1559>3.0.CO;2-E.

Complicated oligosaccharides such as dodecasaccharide 1 can be constructed by a new solid-phase strategy. The attachment to the polymeric support (gray sphere) is through a photolabile linker (structure I), and thioglycosides serve as carbohydrate donors. Bn=benzyl, Bz=benzoyl.

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Nicolaou KC, Watanabe N, Li J, et al. Solid-Phase Synthesis of Oligosaccharides: Construction of a Dodecasaccharide. Angew Chem Int Ed Engl. 1998;37(11):1559-1561doi: 10.1002/(SICI)1521-3773(19980619)37:11<1559::AID-ANIE1559>3.0.CO;2-E.
Nicolaou, K. C., Watanabe, N., Li, J., Pastor, J., & Winssinger, N. (1998). Solid-Phase Synthesis of Oligosaccharides: Construction of a Dodecasaccharide. Angewandte Chemie (International ed. in English), 37(11), 1559-1561. https://doi.org/10.1002/(SICI)1521-3773(19980619)37:11<1559::AID-ANIE1559>3.0.CO;2-E
Nicolaou, K C, et al. "Solid-Phase Synthesis of Oligosaccharides: Construction of a Dodecasaccharide." Angewandte Chemie (International ed. in English) vol. 37,11 (1998): 1559-1561. doi: https://doi.org/10.1002/(SICI)1521-3773(19980619)37:11<1559::AID-ANIE1559>3.0.CO;2-E
Nicolaou KC, Watanabe N, Li J, Pastor J, Winssinger N. Solid-Phase Synthesis of Oligosaccharides: Construction of a Dodecasaccharide. Angew Chem Int Ed Engl. 1998 Jun 19;37(11):1559-1561. doi: 10.1002/(SICI)1521-3773(19980619)37:11<1559::AID-ANIE1559>3.0.CO;2-E. PMID: 29710918.
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Synthesis of fluorinated thiodigalactoside analogues.

Carbohydrate research

St-Gelais J, Leclerc C, Giguère D.
PMID: 34837848
Carbohydr Res. 2021 Nov 20;511:108481. doi: 10.1016/j.carres.2021.108481. Epub 2021 Nov 20.

In this work, we report the first synthesis of fluorinated thiodigalactoside analogues. We used tri-isopropylsilyl thioglycosides as masked glycosyl thiol nucleophiles for the elaboration of two monofluorinated heterodimers, one difluorinated homodimer, and one difluorinated heterodimer. Moreover, we also present...

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St-Gelais J, Leclerc C, Giguère D. Synthesis of fluorinated thiodigalactoside analogues. Carbohydr Res. 2021;511:108481doi: 10.1016/j.carres.2021.108481.
St-Gelais, J., Leclerc, C., & Giguère, D. (2021). Synthesis of fluorinated thiodigalactoside analogues. Carbohydrate research, 511108481. https://doi.org/10.1016/j.carres.2021.108481
St-Gelais, Jacob, et al. "Synthesis of fluorinated thiodigalactoside analogues." Carbohydrate research vol. 511 (2021): 108481. doi: https://doi.org/10.1016/j.carres.2021.108481
St-Gelais J, Leclerc C, Giguère D. Synthesis of fluorinated thiodigalactoside analogues. Carbohydr Res. 2021 Nov 20;511:108481. doi: 10.1016/j.carres.2021.108481. Epub 2021 Nov 20. PMID: 34837848.
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Synthesis and Evaluation of Diverse N-Substituted Disaccharide Dipeptides for Human NOD2 Stimulation Activity.

Chemistry, an Asian journal

Guo CW, Chen KT, You TY, Lin CC, Cheng WC.
PMID: 34951523
Chem Asian J. 2021 Dec 23; doi: 10.1002/asia.202101169. Epub 2021 Dec 23.

A new strategy for the preparation of distinct N -substituted muropeptides is described. Different orthogonally N -protected disaccharide thioglycosides were designed and synthesized. Among them, compound 4 , qualified as a key intermediate, was utilized for further chemical transformations...

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Guo CW, Chen KT, You TY, et al. Synthesis and Evaluation of Diverse N-Substituted Disaccharide Dipeptides for Human NOD2 Stimulation Activity. Chem Asian J. 2021;doi: 10.1002/asia.202101169.
Guo, C. W., Chen, K. T., You, T. Y., Lin, C. C., & Cheng, W. C. (2021). Synthesis and Evaluation of Diverse N-Substituted Disaccharide Dipeptides for Human NOD2 Stimulation Activity. Chemistry, an Asian journal, . https://doi.org/10.1002/asia.202101169
Guo, Chih-Wei, et al. "Synthesis and Evaluation of Diverse N-Substituted Disaccharide Dipeptides for Human NOD2 Stimulation Activity." Chemistry, an Asian journal vol. (2021). doi: https://doi.org/10.1002/asia.202101169
Guo CW, Chen KT, You TY, Lin CC, Cheng WC. Synthesis and Evaluation of Diverse N-Substituted Disaccharide Dipeptides for Human NOD2 Stimulation Activity. Chem Asian J. 2021 Dec 23; doi: 10.1002/asia.202101169. Epub 2021 Dec 23. PMID: 34951523.
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Showing 1 to 12 of 97 entries