A NEW APPROACH TO THE CHEMICAL SYNTHESIS OF THE TRISACCHARIDE, AND THE TERMINAL DISACCHARIDE AND MONOSACCHARIDE UNITS OF THE MAJOR, SEROLOGICALLY ACTIVE GLYCOLIPID FROM MYCOBACTERIUM-LEPRAE

The key intermediates for the synthesis of p-trifluoroacetamidophenyl O-(3,6-di-O-methyl-beta-D-glucopyranosyl)-(1 --> 4(-O-(2,3-di-O-methyl-alpha-L-rhamnopyranosyl)-(1 --> 2)-3-O-methyl-alpha-L-rhamnopyranoside (15), as well as p-trifluoroacetamidophenyl O-(3,6-di-O-methyl-beta-D-glucopyranos...

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Bibliographic Details
Published inCarbohydrate research Vol. 241; pp. 99 - 116
Main Authors BORBAS, A, LIPTAK, A
Format Journal Article
LanguageEnglish
Published AMSTERDAM Elsevier 17.03.1993
Subjects
Biochemistry & Molecular Biology
Chemistry
Chemistry, Applied
Chemistry, Organic
Life Sciences & Biomedicine
Physical Sciences
Science & Technology
PROTECTION
DISACCHARIDES
PHENOLIC GLYCOLIPID-I
SERODIAGNOSIS
ANTIGENS
DERIVATIVES
CARBOHYDRATE-CHEMISTRY
ALLYL GROUP
LEPROSY
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Summary:The key intermediates for the synthesis of p-trifluoroacetamidophenyl O-(3,6-di-O-methyl-beta-D-glucopyranosyl)-(1 --> 4(-O-(2,3-di-O-methyl-alpha-L-rhamnopyranosyl)-(1 --> 2)-3-O-methyl-alpha-L-rhamnopyranoside (15), as well as p-trifluoroacetamidophenyl O-(3,6-di-O-methyl-beta-D-glucopyranosyl)-(1 --> 4)-2,3-di-O-methyl-alpha-L-rhamnopyranoside (29), were the methyl and ethyl O-(2-O-benzyl-4,6-O-benzylidene-3-O-methyl-beta-D-glucopyranosyl)-(1 -->4)-2,3-O-diphenylmethylene-1-thio-alpha-L-rhamnopyranosides (10 and 24). Dichloroalane treatment of 10 and 24 removed the diphenylmethylene group, liberating HO-2 and HO-3 of the rhamnopyranoside residue, and opened the benzylidene acetal regioselectively to give the 4-O-benzyl-glucopyranosyl disaccharides. Methylation of the free OH groups resulted in the tetra-O-methyl 1-thio disaccharides (12 and 26), useful as glycosyl donors. Introduction of these temporary blocking groups allowed a drastic reduction in the number of synthetic steps to the target compounds.
ISSN:0008-6215
DOI:10.1016/0008-6215(93)80099-Z