A. Hasegawa, Y. Kawai, H. Kasugai
Jun 1, 1978
Citations
0
Influential Citations
21
Citations
Journal
Carbohydrate Research
Abstract
Abstract 2-Acetamido-2-deoxy-5-thio- d -glucopyranose (12) has been synthesized from methyl 2-acetamido-2-deoxy-5,6- O -isopropylidene-β- d -glucofuranoside (1) . Benzoylation of 1 , followed by O -deisopropylidenation, gave methyl 2-acetamido-3- O -benzoyl-2-deoxy-β- d -glucofuranoside, which was converted, via selective benzoylation and mesylation, into methyl 2-acetamido-3,6-di- O -benzoyl-2-deoxy-5- O -mesyl-β- d -glucofuranoside (5) . Treatment of 6 , formed by the action of sodium methoxide in chloroform on 5 , with thiourea gave methyl 2-acetamido-2,5,6-trideoxy-5,6-epithio-β- d -glucofuranoside (7) , which was converted into the 5-thio compound 9 by cleavage of the epithio ring in 7 with potassium acetate. Alkaline treatment of 10 , derived from 9 by hydrolysis, afforded the title compound. Evidence in support of the structures assigned to the new derivatives is presented.