[Synthesis of polydeoxygenated and iodinated disaccharides].
3-Amino-polydeoxy disaccharides have been prepared by condensation of a glycal with methyl 2,3,6-trideoxy-alpha-L-erythro-(or threo)-hex-2-enopyranoside in the presence of N-iodosuccinimide. After acid hydrolysis of the glycoside, 1,4-addition of hydrazoic acid to the corresponding hex-2-enopyranose led to 3-azido-disaccharides which were acetylated. Reduction of the azido group gave 2,2'-dideoxy- or 2,2'-dideoxy-2'-iodo compounds. Condensation of O-(3,4-di-O-acetyl-2,6-dideoxy-2-iodo-alpha-L-manno-hexopy-rano syl)-(1----4)-1- O-acetyl-2,3,6-trideoxy-3-trifluoroacetamido-alpha-L-arabino-he xopyranose with daunomycinone, followed by 3',4'-O-deacetylation produced the new anthracycline, 7-O-[O-(2,6-dideoxy-2-iodo-alpha-L-manno-hexopyranosyl)-(1----4)-2,3,6- trideoxy-3-trifluoroacetamido-alpha-L-arabino-hexopyranosyl]-da uno-mycinone.
Abbaci
B
B
Service de Chimie, C.N.R.S., U.R.A. 1387, Institut Curie, Paris, France.
Florent
J C
JC
Monneret
C
C
D002240:Carbohydrate Sequence; D003837:Deoxy Sugars / Q000737:chemistry*; D004187:Disaccharides / Q000138:chemical synthesis*; D008969:Molecular Sequence Data; D013388:Succinimides / Q000737:chemistry
D003837:Deoxy Sugars; D004187:Disaccharides; D013388:Succinimides; C008155:N-iodosuccinimide
Synthèse de disaccharides polydésoxygénés et iodés.