Carbohydrate Research

Acyclic-sugar purine nucleosides derived from d-glucose: stereochemical correlations in acyclic-sugar derivatives unequally substituted at c-1

KC Blieszner, D Horton, RA Markovs

Index: Blieszner, Kathleen C.; Horton, Derek; Markovs, Robert A. Carbohydrate Research, 1980 , vol. 80, p. 241 - 262

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Citation Number: 15

Abstract

Abstract Condensation of 2, 3, 4, 5, 6-penta-O-acetyl-l-bromo-1-s-methyl-l-thio-d-glucito (1) with 6-chloro-9-(chloromercuri) purine gave 49% of crystalline, levorotatory (1s)-2, 3, 4, 5, 6- penta-O-acetyl-1-(6-chloropurin-9-yl)-1-s-methyl-1-thio-d-glucitol (3), together with a smaller proportion of the syrupy, dextrorotatory (1R) isomer. Thiourea converted 3 into its 6- mercaptopurine analog, whose O-deacetylated derivative could be s-methylated to the ...