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

Autor: Glibstrup E; Department of Chemistry, University of Copenhagen , Universitetsparken 5, 2100 Copenhagen Ø, Denmark., Pedersen CM; Department of Chemistry, University of Copenhagen , Universitetsparken 5, 2100 Copenhagen Ø, Denmark.
Jazyk: angličtina
Zdroj: Organic letters [Org Lett] 2016 Sep 02; Vol. 18 (17), pp. 4424-7. Date of Electronic Publication: 2016 Aug 23.
DOI: 10.1021/acs.orglett.6b02241
Abstrakt: 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.
Databáze: MEDLINE