ß elimination in aldonolactones. Synthesis of 3,6 dideoxy L arabino hexose (ascarylose)

O. VARELA; A. FERNÁNDEZ CIRELLI; R. MUCHNIK DE LEDERKREMER

CARBOHYDRATE RESEARCH

Elsevier

Lugar: Amsterdam; Año: 1979 vol. 70 p. 27 - 35

0008-6215

Benzolation of L-rhamnono-1,5-lactone with an excess of benzoyl chloride and pyridine for 16 h afforded 2,4-di-O-benzoyl-3,6-dideoxy-L-erythro-hex-2-enono-1,5-lactone. Catalytic hydrogenation of 2 was stereoselective and gave a crystalline 2,4-di-O-benzoyl-3,6-dideoxy-L-arabino-hexono-1,5-lactone. Reduction of the lactone with disiamylborane afforded 2,4-di-O-benxoyl-3,6-dideoxy-L-arabino-hexopyranose wich, on debenzoylation, gave 3,6-dideoxy-L-arabino-hexose (ascarylose) in good overall yield. THe sugar was identified as the corresponding alditol (ascarylitol) and by convertion into methyl 3,6-dideoxy-L-arabino-hexo-pyranoside (methyl ascaryloside).