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The chemistry of O-silylated ketene acetals; diastereoselective Aldol reaction of 2,3-O-isopropylidene-D (and L)-glyceraldehydes leading to 2-deoxy-D (and L)-riboses
Authors:Yasuyuki Kita  Hitoshi Yasuda  Osamu Tamura  Fumio Itoh  Yasumitsu Tamura
Affiliation:Faculty of Pharmaceutical Sceinces, Osaka University, 1-6, Yamada-oka, Suita, Osaka 565 Japan
Abstract:
Diastereoselective carbon-carbon bond forming reaction of 2,3-O-isopropylidene-D (and L)-glyceraldehydes (D and L-2) with ketene silyl acetals (1a,b) occurred in acetonitrile under mild conditions to give the corresponding anti-β-siloxyesters (D and L-3a) as major products, which could be converted through a few additional steps to 2-deoxy-D(and L)-riboses.
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