A new approach to the chemical synthesis of the trisaccharide, and the terminal di- and mono-saccharide units of the major, serologically active glycoplipid from Mycobacterium leprae

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Abstract

The key intermediates for the synthesis of p-trifluoroacetamidophenyl O-(3,6-di-O-methyl-β-d-glucopyranosyl)-(1 → 4)-O-(2,3-di-O-methyl-α-l-rhamnopyranosyl)-(1 → 2)-3-O-methyl-α-l-rhamnopyranoside (15), as well as p-trifluoroacetamidophenyl O-(3,6-di-O-methyl-β-d-glucopyranosyl)-(1 → 4)-2,3-di-O-methyl-α-l-rhamnopyranoside (29), were the methyl and ethyl O-(2-O-benzyl-4,6-O-benzylidene-3-O-methyl-β-d-glucopyranosyl)-(1 → 4)-2,3-O-diphenylmethylene-1-thio-α-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.

Original languageEnglish
Pages (from-to)99-116
Number of pages18
JournalCarbohydrate Research
Volume241
Issue numberC
DOIs
Publication statusPublished - Mar 17 1993

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ASJC Scopus subject areas

  • Analytical Chemistry
  • Biochemistry
  • Organic Chemistry

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