The synthesis of 5-C-(6-deoxy-1,2:3,4-di-O-isopropylidene-alpha-D-galactopyranos-6-yl)-2 ,3-O-isopropylidene-D-allo-pentofuranose [deaminotri-O-isopropylidene tunicamine].
Three approaches to the synthesis of deaminotunicamine and derivatives were developed. Tin tetrachloride condensation of 6-deoxy-1,2:3,4-di-O-isopropylidene-alpha-D-galacto-heptodialdo-1, 5-pyranose with 2-(trimethylsilyloxy)furan gave a mixture of stereoisomeric precursors. Condensation of 1,2:3,4-di-O-isopropylidene-alpha-D-galacto-hexodialdo-1,5-pyranos e with the phosphate carbanion obtained from diethyl (2-furyl)methoxymethyl phosphonate led to 6-deoxy-7-C-(2-furyl)-1,2:3,4-di-O-isopropylidene-L-glycero-alpha-D- galactoheptopyranose (13). This was converted, via the "delta 2"-butenolide route, to a mixture of stereoisomeric 5-C-(6-deoxy-alpha-D-galactopyranos-6-yl)-pentono-1,4-lacton es of the D-allo and D-talo configuration. In the third approach, 13 was transformed by the "enulose" approach to deamino-tri-(O-isopropylidene)tunicamine.
Ramza
J
J
Institute of Organic Chemistry, Polish Academy of Sciences, Warsaw.
Zamojski
A
A
D000080:Acetals / Q000138:chemical synthesis*; D000900:Anti-Bacterial Agents / Q000737:chemistry*; D002240:Carbohydrate Sequence; D004187:Disaccharides / Q000737:chemistry*; D005688:Galactosamine / Q000031:analogs & derivatives* / Q000737:chemistry; D006017:Glycolipids / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D008969:Molecular Sequence Data; D011741:Pyrimidine Nucleosides; D014312:Trisaccharides / Q000138:chemical synthesis*; D014415:Tunicamycin / Q000737:chemistry; D014498:Uracil
D000080:Acetals; D000900:Anti-Bacterial Agents; D004187:Disaccharides; D006017:Glycolipids; D011741:Pyrimidine Nucleosides; D014312:Trisaccharides; C034696:corynetoxins; D014415:Tunicamycin; C076323:deaminotri-O-isopropylidene tunicamine; C009329:streptovirudin; D014498:Uracil; C076322:tunicamine; D005688:Galactosamine