Stereoselective Syntheses of Glycopyranosyl 2-phenyl- 1,2,3-triazole-4-carboxylates and (4,6-Dimethylpyrimidin-2-yl)1-thioglycopyranosides

Chem. J. Chinese Universities ›› 1993, Vol. 14 ›› Issue (7): 957.

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Stereoselective Syntheses of Glycopyranosyl 2-phenyl- 1,2,3-triazole-4-carboxylates and (4,6-Dimethylpyrimidin-2-yl)1-thioglycopyranosides

YU Jian-Xin, LIU Fang-Min, CHI Xiao-Jun, CAO Ling-Hua

Department of Chemistry, Xinjiang University, Urumqi, 830046

Received:1992-08-08 Revised:1992-12-10 Online:1993-07-24 Published:1993-07-24

Abstract

Abstract: The glycopyranosyl 2-phenyl-1, 2, 3-triazole-4-carboxylates (1 - 9) and (4, 6-dimethylpyrimidin-2-yl)1-thioglycopyranosides (10-13) were obtained with high yields and stereos-electivity from the reaction of glycopyranosyl bromide with sodium 2-phenyl-1, 2, 3-triazole-4-car-boxylate or with 2-mercapto-4, 6-dimethylpyrimidine sodium salt by phase-transfer catalysis under facile conditions.The structures and confagrations of the products were confirmed on the basis of optical rotations, IRand ¹H NMRspectral data.

Key words: Glycosyl triazole-carboxylate, Glycosylthiopyrimidine, 1-Thioglycoside, Stereoselective synthesis

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YU Jian-Xin, LIU Fang-Min, CHI Xiao-Jun, CAO Ling-Hua . Stereoselective Syntheses of Glycopyranosyl 2-phenyl- 1,2,3-triazole-4-carboxylates and (4,6-Dimethylpyrimidin-2-yl)1-thioglycopyranosides[J]. Chem. J. Chinese Universities, 1993, 14(7): 957.

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Stereoselective Syntheses of Glycopyranosyl 2-phenyl- 1,2,3-triazole-4-carboxylates and (4,6-Dimethylpyrimidin-2-yl)1-thioglycopyranosides

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