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2005
Carbohydrates
U 0500
De Novo Enantioselective Syntheses of Galacto-Sugars and Deoxy Sugars via the
Dihydroxylation of Dienoate. — A new strategy for the synthesis of either
27- 192 Iterative
enantiomer of galacto-sugars is developed. In only one step, racemic (V) is produced
in excellent yield from achiral (I). Optically pure (V) are prepared using the Sharpless
asymmetric dihydroxylation. A highly enantio- and diastereoselective procedure for
the preparation of various sugar γ-lactones is developed resulting in the syntheses of
C-4 deoxysugars. By selecting the order of addition, both D- and L-sugars are produced. — (AHMED, M. M.; BERRY, B. P.; HUNTER, T. J.; TOMCIK, D. J.;
O'DOHERTY*, G. A.; Org. Lett. 7 (2005) 4, 745-748; Dep. Chem., W. Va. Univ.,
Morgantown, WV 26506, USA; Eng.) — Steudel
2005
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