Accession Number:

AD0618814

Title:

ACETONATION OF ALDOSE DIETHYL THIOACETALS,

Descriptive Note:

Corporate Author:

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

Personal Author(s):

Report Date:

1965-02-02

Pagination or Media Count:

8.0

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

Subject Categories:

Distribution Statement:

APPROVED FOR PUBLIC RELEASE