Solid-phase de novo synthesis of a (+/-)-2-deoxy-glycoside
Céline Lucchesi1, Amélie Arboré, Sagrario Pascual
1UCO2M, UMR 6011 Centre National de la Recherche Scientifique, Université du Maine, Faculté des Sciences, Avenue Olivier Messiaen, Le Mans Cedex 9, France.
Abstract:
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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