Several new 5-C-alkoxy-D-galactopyranosides, e.g., I, (R=PhCH2, Me) have been obtained by oxidn. of 4-deoxy-alfa-L-threo-hex-4-enopyranosides, e.g., II (easily available from beta-D-galactopyranosides), with 3-ClC6H4CO3H in alc. solvents. They have been converted into the so far unreported L-arabino-hexos-5-ulose and some of its derivs. through hydrolytic and hydrogenolytic steps. Tautomeric equil. for these keto aldoses have been investigated by NMR techniques
NEW SYNTHETIC PATHWAYS TO 5-C-ALKOXYPYRANOSIDES AND TO HEXOS-5-ULOSE DERIVATIVES
CATELANI, GIORGIO;D'ANDREA, FELICIA
1992-01-01
Abstract
Several new 5-C-alkoxy-D-galactopyranosides, e.g., I, (R=PhCH2, Me) have been obtained by oxidn. of 4-deoxy-alfa-L-threo-hex-4-enopyranosides, e.g., II (easily available from beta-D-galactopyranosides), with 3-ClC6H4CO3H in alc. solvents. They have been converted into the so far unreported L-arabino-hexos-5-ulose and some of its derivs. through hydrolytic and hydrogenolytic steps. Tautomeric equil. for these keto aldoses have been investigated by NMR techniquesFile in questo prodotto:
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