Synthesis, Crystal Structure, and Some Reactions of 2,3,4-Tri-O-acetyl-β-D-Galactopyranurono-6, 1-lactone
- 1 April 1992
- journal article
- research article
- Published by Taylor & Francis in Journal of Carbohydrate Chemistry
- Vol. 11 (3) , 287-303
- https://doi.org/10.1080/07328309208017994
Abstract
D-Gluco-, D -galacto-, and D-manno-configurated 6, 1-lactones of uronic acid were synthesized. A new synthetic approach based on the photobromination. hydrolysis, and oxidation of the corresponding 1,6-anhydro sugars is reported. Conformational studies of 2,3,4-tri-O-acetyl-β-D-galactopyranurono-6,l-lactone in crystalline form and in solution were undertaken. First results of selective deacetylation catalyzed by wheat germ lipase are reported.Keywords
This publication has 28 references indexed in Scilit:
- Galacturonsäurederivate. I. Galacturonate aus Acetyl- und Isopropyliden-D-galactopyranosenJournal für Praktische Chemie, 1990
- Synthese mittlerer und großer Ringe, XXV: Synthese funktionalisierter trans‐Hydrindane mit angularer α‐KetoestergruppeEuropean Journal of Inorganic Chemistry, 1989
- Regioselective Hydrolysis of Carbohydrate Secondary Acyl Esters By Lipases1Journal of Carbohydrate Chemistry, 1989
- Syntheses and1H-NMR Studies on Mucin-Type Sugars Chirally Deuterated at the C-6 PositionJournal of Carbohydrate Chemistry, 1988
- Regiospecific functionalization of the monoterpene ether 1,3,3-trimethyl-2-oxabicyclo[2.2.2]octane (1,8-cineole). Synthesis of the useful bridged .gamma.-lactone 1,3-dimethyl-2-oxabicyclo[2.2.2]octan-3 .fwdarw. 5-olideThe Journal of Organic Chemistry, 1987
- Chiral Deuteration at C-6 of 1,6-Anhydrohexose DerivativesJournal of Carbohydrate Chemistry, 1986
- Stereocontrolled synthesis of polyfunctionalized trans-hydrindan systems: a model study toward anisatinThe Journal of Organic Chemistry, 1986
- Syntheses of sugars with a chirally deuterated hydroxymethyl group. Part II. The synthesis of D-(6R)- and (6S)-(6-2H1)-galactose.Agricultural and Biological Chemistry, 1984
- Photobromination of carbohydrate derivatives. VI. Functionalization at C6 of 2,3,4-Tri-O-acetyl-1,6-anhydro-β-D-glucopyranoseAustralian Journal of Chemistry, 1980
- Tri-O-acetyl-β-D-glucopyranurono-6,1-lactoneJournal of the American Chemical Society, 1955