Síntesis de 2 O benzoil 3,4,6, tridesoxi DL treo hexopiranosa, un nuevo ejemplo de síntesis de desoxiazúcares vía reacciones de eliminación ß en aldonolactonas

M. SZNAIDMAN; A. FERNÁNDEZ CIRELLI; R. MUCHNIK DE LEDERKREMER

Anales Asociación Química Argentina

Asociación Química Argentina

Lugar: Buenos Aires; Año: 1982 vol. 70 p. 341 - 348

0365-7124

Hidrogenation of 3-benzoyloxy-6-mehtylpyran-2-one (I) obtained from L-rhamnono-1,5-lactone, yielded crystalline 2-0-benzoyl-3,4,6-trideoxyDL-threo-hexono 1,5-lactone (II) in quantitative tield. Disiamylborane reduction of compound afforded 2-O-benzoyl-3,4,6-trideoxy-DL-threo-hexopyranose (III), which on benzoylation gave 1,2-di-O-benzoyl-3,4,6-trideoxy-DL-threo-hexopyranose (IV). Upon debenzoylation of III, the free trideoxy sugar was obtained.