A robust synthesis of N-glycolyl muramyl dipeptide via azidonitration/reduction

作者：Xing Shuo; Gleason James L^*

来源：Organic and Biomolecular Chemistry, 2015, 13(5): 1515-1520.

DOI：10.1039/c4ob02147a

A novel synthetic route leading to N-glycolyl muramyl dipeptide (MDP), a bacterial glycopeptide of particular interest in studies of nucleotide-binding oligomerization domain-containing protein 2 (NOD2), is described. The synthetic strategy hinges on the alkylation of benzylidene-protected glucal with 2-bromopropionic acid and thus circumvents a challenging and non-reproducible S(N)2 step at the C-3 position of glucosamine derivatives. The subsequent sequence includes an azidonitration and an unusual azide reduction/acylation step via an aza ylide/oxaphospholidine intermediate. This approach generates a protected N-glycolyl MDP that can be either subjected to a one-step global deprotection or differentially deprotected to obtain further derivatives.

• 出版日期2015
• 单位McGill