Iodonium ion-assisted synthesis of a haptenic tetrasaccharide fragment corresponding to the inner cell-wall glycopeptidolipid of Mycobacterium avium serotype 4

Carbohydr Res. 1993 Mar 17:241:153-64. doi: 10.1016/0008-6215(93)80102-k.

Abstract

Condensation of ethyl 2,4-di-O-benzoyl-1-thio-alpha-L-rhamnopyranoside with ethyl 3-O-benzyl-4-O-chloroacetyl-2-O-methyl-1-thio-beta-L-fucopyranoside in the presence of iodonium di-sym-collidine perchlorate afforded exclusively ethyl 2,4-di-O-benzoyl-3-O-(3-O-benzyl-4-O- chloroacetyl-2-O-methyl-alpha-L-fucopyranosyl)-1-thio-alpha-L-rhamnop yra noside. This disaccharide derivative was extended at C-1 with 3-benzyloxycarbonylaminopropyl 6-deoxy-3,4-O-isopropylidene-alpha-L- talopyranoside, using N-iodosuccinimide and triflic acid as the catalyst, to furnish 3-benzyloxycarbonylaminopropyl 6-deoxy-2-O-[2,4-di-O-benzoyl-3-O-(3-O-benzyl-4-O-chloroacetyl-2-O-me thy l- alpha-L-fucopyranosyl)-alpha-L-rhamnopyranosyl]-3,4-O-isopropylidene-alp ha-L- talopyranoside (20). Selective removal of the chloroacetyl group from 20, followed by condensation with ethyl 2,3-di-O-benzoyl-4-O-methyl-1-thio-alpha-L- rhamnopyranoside in the presence of the same thiophilic promoter, yielded a fully protected tetrasaccharide derivative. Deprotection of the latter gave the target compound 3-aminopropyl 6-deoxy-2-O-[3-O-[2-O- methyl-(4-O-methyl-alpha-L-rhamnopyranosyl)-alpha-L-fucopyranosyl]-alpha -L- rhamnopyranosyl]-alpha-L-talopyranoside (1).

MeSH terms

  • Carbohydrate Sequence
  • Cell Wall / chemistry*
  • Disaccharides / chemical synthesis
  • Glycolipids
  • Glycopeptides
  • Haptens / chemistry*
  • Magnetic Resonance Spectroscopy
  • Models, Molecular
  • Molecular Sequence Data
  • Mycobacterium avium Complex / chemistry*
  • Oligosaccharides / chemical synthesis*
  • Onium Compounds / chemistry
  • Pyridines / chemistry
  • Stereoisomerism
  • Trisaccharides / chemical synthesis

Substances

  • Disaccharides
  • Glycolipids
  • Glycopeptides
  • Haptens
  • Oligosaccharides
  • Onium Compounds
  • Pyridines
  • Trisaccharides
  • peptidoglycolipids
  • 3-aminopropyl 6-deoxy-2-O-(3-O-(2-O-methyl-(4-O-methylrhamnopyranosyl)fucopyranosyl)rhamnopyranosyl)talopyranoside
  • iodonium dicollidine