All-alpha-D-linked tetra- and penta-saccharide substructures of Trestatin A by block syntheses with triflic anhydride as promoter

Carbohydr Res. 1993 Apr 7:242:141-51. doi: 10.1016/0008-6215(93)80028-d.

Abstract

The perbenzylated maltosyl and maltotriosyl fluorides 6 and 16 were treated with 2,3,2',3',6'-penta-O-benzyl-4,6-O-benzylidene-alpha,alpha-trehalose (7) using triflic anhydride as a promoter to give all-alpha-D-linked tetra- and penta-saccharides which were finally deblocked to the free oligosaccharides 4-O-alpha-maltosyl-9 and 4-O-alpha-maltotriosyl-alpha,alpha-trehaloses 18. The 1H NMR spectra of some of the compounds were fully analyzed by 1D TOCSY and ROESY experiments.

MeSH terms

  • Anhydrides
  • Carbohydrate Conformation
  • Carbohydrate Sequence
  • Indicators and Reagents
  • Magnetic Resonance Spectroscopy
  • Molecular Sequence Data
  • Oligosaccharides / chemical synthesis*
  • Oligosaccharides / chemistry
  • Optical Rotation
  • Spectrometry, Mass, Fast Atom Bombardment
  • Trisaccharides / chemical synthesis*
  • Trisaccharides / chemistry

Substances

  • Anhydrides
  • Indicators and Reagents
  • Oligosaccharides
  • Trisaccharides
  • trestatin