Pentenyl glycoside methodology

Rodebaugh, R. Joshi, S. Fraser-Reid, B. Geysen, H. M. Polymer-Supported Oligosaccharides via n-Pentenyl Glycosides Methodology for a Carbohydrate Library, J. Org. Chem. 1997, 62, 5660. 

J. R. Merritt and B. Fraser-Reid, n-Pentenyl glycoside methodology for rapid assembly of homo-glycans exemplified with the nonasaccharide component of a high-mannose glycoprotein, J. Am. Chem. Soc., 114 (1992) 8334-8336. 

R. Rodebaugh, S. Joshi, B. Fraser-Reid, FI. M. Geysen. Polymer-supported oligosaccharides via n-pentenyl glycosides Methodology fora carbohydrate library. J. Org. Chem. 1997.62,5660-5661. 

This observation opened a route to so-called pentenyl glycoside methodology [32, 33], which is now one of the most important methods of the creation of the glycosidic bond. 

B. G. Wilson and B. Fraser-Reid, n-Pentenyl glycoside based methodology for determining the relative reactivities of variously protected pairs of glycosides, /. Org. Chem., 60 (1995) 317-320. 

The application of vinyl glycosides as glycosyl donors has, overall, been less successful than that of trichloroacetimidates or n-pentenyl glycosides. However, several different approaches have been taken by a number of different research groups and the work of Boons and co-workers in particular has led to some useful methodology with general applicability in oligosaccharide assembly. 

Although the methodology introduced by Sinay and advanced by Chenault does essentially work, glycoside synthesis using such vinyl ethers has no definite advantage over methods such as the trichloroacetimidate or n-pentenyl approaches detailed above and suffers from relatively non-trivial procedures required in the preparation of the donor species. However, a useful application of vinyl glycosides in oligosaccharide synthesis has subsequently been developed and applied successfully by Boons. 

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