The Journal of Organic Chemistry

Total synthesis of carbohydrates: stereoselective syntheses of 2, 6-dideoxy-D-arabino-hexose and 2, 6-dideoxy-D-ribo-hexose

WR Roush, RJ Brown

Index: Roush, William R.; Brown, Richard J. Journal of Organic Chemistry, 1982 , vol. 47, # 7 p. 1371 - 1373

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Citation Number: 76

Abstract

Summary: Short, highly stereoselective syntheses of the title carbohydrates from allylic alcohol precursors are described. A synthesis of the racemic arabino-deoxyhexose is also described. These syntheses feature the highly re-gioselective epoxide ring opening reactions of intermediates 7, 11, and 12 and the asymmetric epoxidation-kinetic resolution of allylic alcohol 10.