Chimie et pharmacologie de l'apiose III. Synthèse et propriétés de l'hydrate de l'O‐isopropylidène‐1, 2‐tétrosulo‐3‐furannose

Abstract

Abstract Ruthenium tetroxide oxidation of 1, 2‐O‐isopropylidene‐β‐ D ‐threofuranose affords, besides the known 1, 2‐O‐isopropylidene‐α‐ L ‐ glycero ‐tetros‐3‐ulofuranose, a lactone. The tetrosulose is easily hydrated to the corresponding gem ‐diol whose dehydration on molecular sieves leads to a branched‐chain dimer. Lead tetraacetate oxidation of 1, 2‐O‐isopropylidene‐α‐ L ‐ glycero ‐tetros‐3‐ulofuranose p ‐nitrophenylhydrazone leads quantitatively, to a gem ‐azoacetate, a new synthetic intermediate in carbohydrate chemistry. The 3‐O‐acetyl‐1, 2‐O‐isopropylidene‐α‐ L ‐ glycero ‐tetr‐3‐enofuranose is easily obtained from the gem ‐diol. A highly stereoselective procedure is described to prepare the 3‐O‐acetyl‐1, 2‐O‐isopropylidene‐α‐ L ‐3, 4‐ exo ‐D 2 ‐erythrofuranose.