Glycosylimidates, 54. Synthesis of the GlcNAcβ(1→4)MurNAcβ(1→4)GlcNAcβ(1→4)MurNAc tetrasaccharide of bacterial peptidoglycan

✍ Scribed by Termin, Andreas ;Schmidt, Richard R.

• Publisher: John Wiley and Sons
• Year: 1992
• Tongue: English
• Weight: 738 KB
• Volume: 1992
• Category: Article
• ISSN: 0947-3440
• DOI: 10.1002/jlac.199219920191

✦ Synopsis

Abstract

From 2‐azido‐2‐deoxy‐D‐glucose have been prepared at 1‐O and/or 4‐O selectively protected glucosamine and muramic acid derivatives, which were transformed into glycosyl donors 6 and 14a, b and into glycosyl acceptors 7 and 15. The reaction of these donors and acceptors yielded disaccharides 8 and 11–13. Selective 1a‐O‐deprotection of disaccharide 12 and subsequent treatment with trichloroacetonitrile afforded disaccharide donor 17; selective removal of the 4b‐O‐protective groups in disaccharides 8 and 11 furnished disaccharide acceptor 9. These building blocks were employed in the synthesis of β‐connected tetrasaccharide 18 which gave upon azido group reduction, acetylation of the amino groups, and complete O‐deprotection the desired target molecule 1 characterized as its fully O‐acetylated product 2.