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Kadokawa JI, Yamamoto M, Tagaya H, et al. Synthesis of branched polysaccharides by polymerization of 6-O-t-butyldimethylsilyl-D-glucal through stereoregular haloglycosylation. Carbohydr Lett. 2001;4(2):97-101
Kadokawa, J. I., Yamamoto, M., Tagaya, H., & Chiba, K. (2001). Synthesis of branched polysaccharides by polymerization of 6-O-t-butyldimethylsilyl-D-glucal through stereoregular haloglycosylation. Carbohydrate letters, 4(2), 97-101.
Kadokawa, J I, et al. "Synthesis of branched polysaccharides by polymerization of 6-O-t-butyldimethylsilyl-D-glucal through stereoregular haloglycosylation." Carbohydrate letters vol. 4,2 (2001): 97-101.
Kadokawa JI, Yamamoto M, Tagaya H, Chiba K. Synthesis of branched polysaccharides by polymerization of 6-O-t-butyldimethylsilyl-D-glucal through stereoregular haloglycosylation. Carbohydr Lett. 2001;4(2):97-101. PMID: 11506164.
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Carbohydr Lett. 2001;4(2):97-101.

Synthesis of branched polysaccharides by polymerization of 6-O-t-butyldimethylsilyl-D-glucal through stereoregular haloglycosylation.

Carbohydrate letters

J I Kadokawa, M Yamamoto, H Tagaya, K Chiba

Affiliations

  1. Department of Chemistry and Chemical Engineering, Faculty of Engineering, Yamagata University, Yonezawa, Japan.

PMID: 11506164

Abstract

In this letter, we report synthesis of branched polysaccharide 2 by glycosylation of glucal-type monomer 1 with two free hydroxy groups at position 3 and 4. Monomer 1 polymerized with N-halosuccinimide promoter in acetonitrile solvent at room temperature--50 degrees C. The product was isolated as a petroleum ether insoluble fraction. The structure was determined by 1H and 13C NMR spectra as well as elemental analysis to be a polysaccharide consisting of 2-halo-2-deoxy-alpha-D-mannoside units, indicating that the polymerization proceeded via stereoregular glycosylation manner. The molecular weights determined by GPC with DMF were 3,300-4,000. The degree of branching was estimated by the NMR data of the product from the reaction of 2 with 3,5-dinitrobenzoyl chloride.

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