Synthesis of 2-C- and 3-C-aryl pyranosides

Article abstract of DOI:10.1080/07328309808007461

Lithium diphenylcuprate treatment of methyl 2,3-anhydro-4,6-O-benzylidene-D-pyranosides in which the anomeric substituent and the three-membered rings are cis oriented furnished the expected trans-diaxial opening products. When the relationship between the anomeric group and the epoxide was trans, the same experimental conditions led only to recovered starting material. Cyano cuprates of the type R₂CuCNLi₂ added stereoselectively to carbohydrate ketones at C-2 and C-3 from the opposite side relative to the anomeric substituent.

Full text of DOI:10.1080/07328309808007461

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Journal of Carbohydrate Chemistry
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Synthesis of 2-C- and 3-C-Aryl
Pyranosides
I. Hladezuk a , A. Olesker a , J. Cléophax a & G. Lukacs a
a Institut de Chimie des Substances Naturelles, C.N.R.S. , Avenue de
la Terrasse, 91198, Gif-sur-Yvette, France
Published online: 18 Aug 2006.
To cite this article: I. Hladezuk , A. Olesker , J. Cléophax & G. Lukacs (1998) Synthesis of 2-C- and 3-
C-Aryl Pyranosides, Journal of Carbohydrate Chemistry, 17:6, 869-878
To link to this article: http://dx.doi.org/10.1080/07328309808007461
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