Accession Number : AD0618814

Title :   ACETONATION OF ALDOSE DIETHYL THIOACETALS,

Corporate Author : NATIONAL RESEARCH COUNCIL OF CANADA SASKATOON (SASKATCHEWAN) PRAIRIE REGIONAL LAB

Personal Author(s) : Gorin,P. A. J.

Report Date : 02 FEB 1965

Pagination or Media Count : 8

Abstract : Acetonation of hexose diethyl thioacetals using copper sulphate catalyst gave rise to 5,6-O-substituted products. The exception was D-galactose diethyl thioacetal, which underwent some 4,5-O-substitution. D-Threose and 2,3-di-O-methyl-D-galactose diethyl thioacetals also underwent predominant alpha-terminal substitution although some beta-terminal substitution took place, particularly with the latter thioacetal. Acetone-sulphuric acid caused preferential alpha-T acetonation of D-threose and 2,3-di-O-methyl-D-galactose diethyl thioacetals. The product from D-threose diethyl thioacetal contained 90% of the 2,3-O-isopropylidene and 10% of the 3,4-O-isopropylidene derivatives. D-Glucurono-delta-lactone diethyl thioacetal in acetone-sulphuric acid acetonated mainly on the 2,4- positions although a smaller proportion of 4,5-Oisopropylidene derivative was present. (Author)

Descriptors :   (*MONOSACCHARIDES, SUBSTITUTION REACTIONS), (*HEXOSES, SUBSTITUTION REACTIONS), (*ORGANIC SULFUR COMPOUNDS, SUBSTITUTION REACTIONS), CATALYSTS, KETONES, LACTONES, CHROMATOGRAPHIC ANALYSIS, CANADA

Distribution Statement : APPROVED FOR PUBLIC RELEASE