C. Warren, Nasir-ud-din, R. Jeanloz
Jul 1, 1978
Citations
0
Influential Citations
13
Citations
Journal
Carbohydrate Research
Abstract
Abstract Methyl 2-acetamido-3- O -allyl-2-deoxy-4-O-methyl-α- D -glucopyranoside, methyl 2-acetamido-2-deoxy-4-O-methyl-α- D -glucopyranoside, and methyl 2-acetamido-3,4-di- O -allyl-2-deoxy-α- D -glucopyranoside, prepared from methyl 2-acetamido-2-deoxy-α- D -glucopyranoside, were coupled with 2,3,4,6-tetra- O -acetyl-α- D -glucopyranosyl phosphate ( 13 ), to give the phosphoric esters methyl 2-acetamido-3- O -allyl-2-deoxy-4- O -methyl-α- D -glucopyranoside 6-(2,3,4,6-tetra- O -acetyl-α- D -glucopyranosyl phosphate) ( 16 ), methyl 2-acetamido-2-deoxy-4- O -methyl-α- D -glucopyranoside 6-(2,3,4,6-tetra- O -acetyl-α- D -glucopyranosyl phosphate) ( 23 ), and methyl 2-acetamido-3,4-di- O -allyl-2-deoxy-α- D -glucopyranoside 6-(2,3,4,6-tetra- O -acetyl-α- D -glucopyranosyl phosphate) ( 17 ). Compound 13 was prepared from penta- O -acetyl-β- D -glucopyranose by the phosphoric acid procedure, or by acetylation of α- D -glucopyranosyl phosphate. Removal of the allyl groups from 16 and 17 gave 23 and methyl 2-acetamido-2-deoxy-α- D -glucopyranoside 6-(2,3,4,6-tetra- O -acetyl-α- D -glucopyranosyl phosphate) ( 19 ), respectively. O -Deacetylation of 23 gave methyl 2-acetamido-2-deoxy-4- O -methyl-α- D -glucopyranoside 6-(α- D -glucopyranosyl phosphate) ( 26 ) and O -deacetylation of 19 gave methyl 2-acetamido-2-deoxy-α- D -glucopyranoside 6-(α- D -glucopyranosyl phosphate) ( 24 ). Propyl 2-acetamido-2-deoxy-α- D -glucopyranoside 6-(α- D -glucopyranosyl phosphate) ( 25 ) was prepared by coupling 13 with allyl 2-acetamido-3,4-di- O -benzyl-2-deoxy-α- D -glucopyranoside, followed by catalytic hydrogenation of the product to give the propyl glycoside, which was then O -deacetylated. Compounds 24, 25, and 26 are being employed in structural studies of the Micrococcus lysodeikticus cell-wall.