Reaction of organocuprate reagents with protected 1,2-anhydro sugars. Stereocontrolled synthesis of 2-deoxy-C-glycosyl compounds |
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Authors: | Véronique Bellosta Stanislas Czernecki |
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Affiliation: | 1. Laboratoire de Recherches Organiques, UA CNRS 476, ESPCI 10, Rue Vauquelin, 75005 Paris France;2. Laboratoire de Chimie des Glucides, Université Pierre et Marie Curie, Tour 74/4 Place Jussieu, 75005 Paris France |
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Abstract: | The reaction of protected 1,2-anhydro-α-d-gluco- and β-d-manno-pyranoses with alkyl and phenyl organocuprates afforded the corresponding C-glycosyl compounds in acceptable to high yield. Complete stereocontrol was obtained, leading respectively to the β-d or the α-d anomer. With the perbenzylated manno derivative, deoxygenation at C-2 was achieved in high yield, affording 2-deoxy-α-d-C-glycosyl compounds. |
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Keywords: | Author for correspondence. |
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