Anthracycline oligosaccharides: facile stereoselective synthesis of 2,6-dideoxy-alpha-L-lyxo-hexopyranosides.
Glycosylation of benzyl-2,3,6-trideoxy-3-trifluoroacetamido-alpha-L-lyxo-h exopyranoside (6) with 3,4-di-O-acetyl-1,5-anhydro-2,6-dideoxy-L-lyxo-hex-1-enitol (1) or 4-O-acetyl-1,5-anhydro-3-O-benzyl-2,6-dideoxy-L-lyxo-hex-1-enit ol (2) in the presence of trimethylsilyl triflate/triethylamine gave alpha-(1----4)-linked disaccharide derivatives 7 and 8, respectively. In the presence of trimethylsilyl triflate only, 3,4-di-O-acetyl-1-O-tert-butyldimethylsilyl-2,6-dideoxy-beta-L-lyxo++ +-hexopyranose (3) and 6 gave mainly 7. Condensation of 1 or 2 with 9, obtained by O-deacylation of 8, afforded benzyl [O-(3,4-di-O-acetyl-2,6-dideoxy-alpha-L-lyso-hexopyranosyl)-(1----4)-O-( 3-O-benzyl-2,6-dideoxy-2,6-alpha-L-hexopyranosyl)-(1----4)-(2,3,6-tri deo xy-3-trifluoroacetamido-alpha-L-lyxo-hexopyranoside)] (11) and its 3''-benzyl analogue 12, respectively.
Kolar
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Research Laboratories of Behringwerke AG, Marburg F.R.G.
Kneissl
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Wolf
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Kämpchen
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D000903:Antibiotics, Antineoplastic / Q000138:chemical synthesis*; D002236:Carbohydrate Conformation; D002240:Carbohydrate Sequence; D004187:Disaccharides / Q000138:chemical synthesis; D006031:Glycosylation; D008969:Molecular Sequence Data; D015394:Molecular Structure; D009844:Oligosaccharides / Q000138:chemical synthesis*; D014312:Trisaccharides / Q000138:chemical synthesis
D000903:Antibiotics, Antineoplastic; D004187:Disaccharides; D009844:Oligosaccharides; D014312:Trisaccharides