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Glibstrup E, Pedersen CM. Scalable Synthesis of Anomerically Pure Orthogonal-Protected GlcN3 and GalN3 from d-Glucosamine. Org Lett. 2016;18(17):4424-7doi: 10.1021/acs.orglett.6b02241.
Glibstrup, E., & Pedersen, C. M. (2016). Scalable Synthesis of Anomerically Pure Orthogonal-Protected GlcN3 and GalN3 from d-Glucosamine. Organic letters, 18(17), 4424-7. https://doi.org/10.1021/acs.orglett.6b02241
Glibstrup, Emil, and Pedersen, Christian Marcus. "Scalable Synthesis of Anomerically Pure Orthogonal-Protected GlcN3 and GalN3 from d-Glucosamine." Organic letters vol. 18,17 (2016): 4424-7. doi: https://doi.org/10.1021/acs.orglett.6b02241
Glibstrup E, Pedersen CM. Scalable Synthesis of Anomerically Pure Orthogonal-Protected GlcN3 and GalN3 from d-Glucosamine. Org Lett. 2016 Sep 02;18(17):4424-7. doi: 10.1021/acs.orglett.6b02241. Epub 2016 Aug 23. PMID: 27552399.
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Org Lett. 2016 Sep 02;18(17):4424-7. doi: 10.1021/acs.orglett.6b02241. Epub 2016 Aug 23.

Scalable Synthesis of Anomerically Pure Orthogonal-Protected GlcN3 and GalN3 from d-Glucosamine.

Organic letters

Emil Glibstrup, Christian Marcus Pedersen

Affiliations

  1. Department of Chemistry, University of Copenhagen , Universitetsparken 5, 2100 Copenhagen Ø, Denmark.

PMID: 27552399 DOI: 10.1021/acs.orglett.6b02241

Abstract

An improved and scalable synthesis of orthogonally protected d-glucosamine and d-galactosamine building blocks from inexpensive d-glucosamine has been developed. The key reaction is an inversion/migration step providing access to a fully orthogonal protecting group pattern, which is required for microbial oligosaccharide synthesis. The method can be carried out on a multigram scale as several of the reactions can be purified by crystallization to give anomerically pure products.

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