Multi-Gram Synthesis of a Hyaluronic Acid Subunit and Synthesis of Fully Protected Oligomers

✍ Scribed by Mickaël Virlouvet; Michael Gartner; Katarzyna Koroniak; Jonathan P. Sleeman; Stefan Bräse

• Book ID: 101426872
• Publisher: John Wiley and Sons
• Year: 2010
• Tongue: English
• Weight: 234 KB
• Volume: 352
• Category: Article
• ISSN: 1615-4150
• DOI: 10.1002/adsc.201000008

✦ Synopsis

Abstract

Fully protected tetra‐, hexa‐ and octasaccharides of hyaluronic acid were synthesized on a scale of several 100 mg up to gram quantities using allyl (methyl 2‐O‐benzoyl‐3‐O‐benzyl‐4‐O‐levulinoyl‐β‐D‐glucopyranosyluronate)‐(1→3)‐4‐O‐acetyl‐6‐O‐benzyl‐2‐deoxy‐2‐trichloroacetamido‐β‐D‐glucopyranoside as a key building block. This disaccharide was subjected to deprotection, then glycosylation via the trichloroacetimidate method was employed to achieve the formation of the oligosaccharides.