New syntheses of 2′-C-methylnucleosides starting from D-glucose and D-ribose

LN Beigelman, BS Ermolinsky, GV Gurskaya…

Index: Beigelman, Leon N.; Ermolinsky, Boris S.; Gurskaya, Galina V.; Tsapkina, Elena N.; Karpeisky, Marat Ya.; Mikhailov, Sergey N. Carbohydrate Research, 1987 ,  vol. 166, p. 219 - 232

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Citation Number: 45

Abstract

Abstract Effective general methods have been developed for the synthesis of 2′-C- methylnucleosides starting from d-glucose and d-ribose. 3-O-benzyl-1, 2-O-isopropylidene-3- C-methyl-α-d-allofuranose was prepared in 5 steps from d-glucose and converted into 1, 2, 3- tri-O-acetyl-2-C-methyl-5-Op-methylbenzoyl-d-ribofuranose (5), the starting compound for nucleoside synthesis. Compound 5 was also synthesised from 2-C-hydroxymethyl-2, 3-O- ...