Glycosylation with N-Troc-protected glycosyl donors

✍ Scribed by Ulf Ellervik; Göran Magnusson

• Publisher: Elsevier Science
• Year: 1996
• Tongue: English
• Weight: 580 KB
• Volume: 280
• Category: Article
• ISSN: 0008-6215
• DOI: 10.1016/0008-6215(95)00318-5

✦ Synopsis

N-Troc-protected (Troc = 2,2,2-trichloroethoxycarbonyl) glucosamine and galactosamine glycosyl donors (1-O-acetyl sugar, bromo sugar, and thioglycoside) were compared with the corresponding N-Phth-protected derivatives in glycosylations of 2-(trimethylsilyl)ethanol, 2-bromoethanol, methyl 3-mercaptopropionate, N-Fmoc-protected serine, and 2-(trimethylsilyl)ethyl 6-O-benzyl-2-deoxy-2-phthalimido-beta-D-glucopyranoside. The N-Troc-protected donors gave pure beta-glycosides in somewhat higher yields than the N-Phth-protected counterparts. The N-Troc protecting group can be removed by reduction with zinc, which allows selective N-deprotection in oligosaccharides containing both N-Troc and N-Phth groups.