â-elimination in aldonolactones. Synthesis of 2-deoxy- -lyxo-hexose and 2-deoxy- -arabino-hexose

L. SALA; A. FERNÁNDEZ CIRELLI; R. MUCHNIK DE LEDERKREMER

CARBOHYDRATE RESEARCH

Elsevier

Lugar: Amsterdam; Año: 1980 vol. 78 p. 61 - 66

0008-6215

Benzoylation of -glycero- -manno-heptono-1,4-lactone (1) with benzoyl chloride and pyridine for 2 h afforded crystalline penta-O-benzoyl- -glycero- -manno-heptono-1,4-lactone (2), but a large excess of reagent during 8 h also led to 2,5,6,7-tetra-O- benzoyl-3-deoxy- -lyxo-hept-2-enono-1,4-lactone (3). Catalytic hydrogenation of 3 was stereoselective and gave 2,5,6,7-tetra-O-benzoyl-3-deoxy- -galacto-heptono-1,4-lactone (4). Debenzoylation of 4 followed by oxidative decarboxylation with ceric sulfate in aqueous sulfuric acid gave 2-deoxy- -lyxo-hexose (5). Application of the same reaction to 3-deoxy- -gluco-heptono-1,4-lactone afforded 2-deoxy- -arabino-hexose (6).