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Dioxolane and dioxane acetal derivatives of D allose: condensation of 3 O benzyl D allose with acetaldehyde

Author:
Dick, W.E., Weisleder, D., Hodge, J.E.
Source:
Carbohydrate research 1975 v.42 no.1 pp. 55
ISSN:
0008-6215
Subject:
dioxane, acetaldehyde, chemical reactions, nuclear magnetic resonance spectroscopy
Abstract:
Condensation of 3-O-benzyl-D-allose with acetaldehyde forms a complex mixture from which potentially useful mono- and di-O-ethylidene derivatives were isolated and identified. Compounds isolated and identified after conversion of unsubstituted hydroxyl groups into the corresponding acetates included 1,2-di-O-acetyl-3-O-benzyl-4,6-O-ethylidene-β-D-allopyranose; 5,6-di-O-acetyl-3-O-benzyl-1,2-O-(R)-ethylidene-α-D-allofuranose; and two 3-O-benzyl-1,2:5,6-di-O-ethylidene-α-D-allofuranoses, both having the R configuration in the 1,2-O-ethylidene ring. Furanose and pyranose conformations were determined by n.m.r. analysis, and the location and configuration of each acetal ring was established. The benzyl ether group in the furanose derivatives was removed by catalytic hydrogenation with subsequent formation of 3-O-acetyl analogs.
Agid:
29554
Handle:
10113/29554