All-alpha-D-linked tetra- and penta-saccharide substructures of Trestatin A by block syntheses with triflic anhydride as promoter.
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.
F. Hoffmann-La Roche Ltd, Pharma Division, Preclinical Research and New Technologies, Basel, Switzerland.
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Wessel
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Mayer
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Englert
D000812:Anhydrides; D002236:Carbohydrate Conformation; D002240:Carbohydrate Sequence; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D008969:Molecular Sequence Data; D009844:Oligosaccharides / Q000138:chemical synthesis* / Q000737:chemistry; D009904:Optical Rotation; D016339:Spectrometry, Mass, Fast Atom Bombardment; D014312:Trisaccharides / Q000138:chemical synthesis* / Q000737:chemistry
D000812:Anhydrides; D007202:Indicators and Reagents; D009844:Oligosaccharides; D014312:Trisaccharides; C038505:trestatin