Semi-orthogonality of O-pentenyl and S-ethyl glycosides: application for the oligosaccharide synthesis

✍ Scribed by Alexei V. Demchenko; Cristina De Meo

• Publisher: Elsevier Science
• Year: 2002
• Tongue: French
• Weight: 147 KB
• Volume: 43
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(02)02235-9

✦ Synopsis

Novel semi-orthogonal glycosylation strategy with the use of O-pentenyl and thioglycosides has been developed. According to this technique both armed and disarmed thioglycosides can be selectively activated with MeOTf in the presence of either armed or disarmed O-pentenyl glycosides. The applicability of this novel strategy for the synthesis of a trans-cis glycosylation pattern, not accessible via conventional armed-disarmed approach, has been demonstrated for the synthesis of a linear tetrasaccharide derivative.