Solid-phase de novo synthesis of a (+/-)-2-deoxy-glycoside.

Carbohydr Res

UCO2M, UMR 6011 Centre National de la Recherche Scientifique, Université du Maine, Faculté des Sciences, Avenue Olivier Messiaen, Le Mans Cedex 9, France.

Published: April 2010

The solid-phase synthesis of methyl 2-deoxy-3-O-benzyl-D,L-arabino-hexopyranoside was achieved in a six-step sequence via a de novo strategy based on the hetero-Diels-Alder reaction of a vinyl ether supported on an azalactone-functionalized polystyrene resin, followed by the functional modification of the heteroadduct and the final release of the methyl glycoside by acidic solvolysis.

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http://dx.doi.org/10.1016/j.carres.2010.01.017DOI Listing

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