Synthesis of p-trifluoroacetamidophenyl (4,6-dideoxy-4-formamido-3-C-methyl-2-O-methyl-α-L-mannopyran osyl)-(1→3)-(2-O - methyl-α-D-rhamnopyranosyl)-(1→3)-(2-O-methyl-α-L-fucopyran osyl)-(1 →3)-(α-L-rhamnopyranosyl)-(1 →2)-6-deoxy-α-L-talopyranoside: A spacer-armed pentasaccharide glycopeptidolipid antigen of Mycobacterium avium serovar 14

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Abstract

Syntheses of p-trifluoroacetamidophenyl glycosides of the haptenic pentasaccharide and the non-reducing disaccharide unit of the title pentasaccharide are reported. The synthesis of the terminal N-formylkansosamine unit started from methyl 6-deoxy-2,3-O-isopropylidene-α-L-lyxo-hexopyran-4- uloside which, after C-3 methylation, was transformed into a glycosyl donor [3-O-benzyl-4-N-benzylformamido-4,6-dideoxy-3-C- methyl-2-O-methyl-α,β-L-mannopyranosyl trichloroacetimidate (20), and used for the synthesis of p-trifluoroacetamidophenyl (4-formamido-4,6-dideoxy-3-C-methyl-2-O-methyl-α-L-mannopyran osyl)- (1→3)-6-deoxy-2-O-methyl-α-D-mannopyrano (29). Ethyl (3-O-benzyl-4-N-benzylformamido-4,6-dideoxy-3-C-methyl-2-O-met hyl-α-L -mannopyranosyl)-(1→3)-4-O-benzyl-6-deoxy-2-O-methyl- 1-thio-α-D-nannopyranoside (31), prepared by glycosylation of ethyl 4-O-benzyl-6-deoxy-2-O-methyl-1-thio-α-D-mannopyranoside with 20, served as glycosyl donor in a 2 + 3 block synthesis of the title pentasaccharide.

Original languageEnglish
Pages (from-to)247-258
Number of pages12
JournalCarbohydrate Research
Volume308
Issue number3-4
DOIs
Publication statusPublished - Apr 1 1998

Keywords

  • Block synthesis
  • Branched-chain sugar
  • Oligosaccharide synthesis
  • Spacer
  • p-Trifluoroacetamidophenyl

ASJC Scopus subject areas

  • Analytical Chemistry
  • Biochemistry
  • Organic Chemistry

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