Carbohydrate Research

Stereochemical control as a function of protecting-group participation in 2-deoxy-D-erythro-pentofuranosyl nucleosides

W Wierenga, HI Skulnick

Index: Wierenga, Wendell; Skulnick, Harvey I. Carbohydrate Research, 1981 , vol. 90, p. 41 - 52

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Citation Number: 36

Abstract

Abstract Possible features controlling the anomeric ratios in the synthesis of the antiviral antibiotic dihydro-5-azathymidine have been examined. Replacement of the 3-and 5-(4- methylbenzoyl) protecting groups in 2-deoxy-D-erythro-pentofuranosyl chloride by benzyl groups led to changes in anomeric ratios in stannic chloride-mediated condensations with both 5-methyl-2, 4-bis (trimethylsilyl) triazine and 2, 4-bis (trimethylsilyl) thymine. Analysis ...