Reducing oligosaccharides via glycal assembly: on the remarkable stability of anomeric hydroxyl groups to global deprotection with sodium in liquid ammonia

✍ Scribed by Ulrich Iserloh; Vadim Dudkin; Zhi-Guang Wang; Samuel J Danishefsky

• Publisher: Elsevier Science
• Year: 2002
• Tongue: French
• Weight: 95 KB
• Volume: 43
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(02)01551-4

✦ Synopsis

Several partially benzylated 1-hydroxy sugars were rapidly deprotected by sodium/liquid ammonia. The terminal hemiketal linkage of the substrates remained intact under these conditions and does not generate ring-opened alditols. Peracetylated glucose and glucosamine derivatives were obtained in 64-79% isolated yields.