A robust synthesis of N-glycolyl muramyl dipeptide via azidonitration/reduction. Issue 5 (5th December 2014)

• Record Type: Journal Article
• Authors: Xing, Shuo; Gleason, James L.
• Is Part Of: Organic & biomolecular chemistry. Volume 13:Issue 5(2015)
• Page Start: 1515
• Page End: 1520
• Publication Date: 2014-12-05
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/c4ob02147a
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : Glycal etherification followed by azidonitration/reduction solves a difficult SN 2 step in the synthesis of N -glycolyl muramyl dipeptide. Abstract : 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 SN 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.