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- Title
Utlisation d'ylides du phosphore en chimie des sucres. XIII. Synthèse de dérivés des hydroxyméthyl-3- D-glucose et- D-galactose et de composés voisins.
- Authors
Tronchet, J. M. J.; Bourgeois, J. M.
- Abstract
The treatment of the 1, 2:5, 6-di-O-isopropylidene-α- D- ribo- and xylo-hexofuranos-3-uloses with cyanomethylenetriphenylphosphorane led in each case, and in almost quantitative yields, to a pair of geometrical isomers of C-cyanomethylenic sugars having respectively the ribo and the xylo configurations. Permanganate oxidation of these branched-chain unsaturated sugars afforded the corresponding gem-hydroxyformyl compounds bearing the formyl group on the more hindered face of the molecule. The formyl group of these sugars is easily derivatized to an oximino or reduced to a hydroxymethyl. The configuration at the new asymmetric carbon has been established by comparison with known compounds or by synthesis of a C(3) epimer by the classical route involving a Grignard reagent.
- Publication
Helvetica Chimica Acta, 1972, Vol 55, Issue 8, p2820
- ISSN
0018-019X
- Publication type
Article
- DOI
10.1002/hlca.19720550813