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

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 applicabili...

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Bibliographic Details
Published in:Tetrahedron letters 2002-12, Vol.43 (49), p.8819-8822
Main Authors: Demchenko, Alexei V., De Meo, Cristina
Format: Article
Language:English
Subjects:
chemoselectivity
glycosyl donors
glycosylation
novel synthetic strategy
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Summary: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. Graphic
ISSN:0040-4039
1873-3581
DOI:10.1016/S0040-4039(02)02235-9