R. T. Lee, Yuan-chuan Lee
May 1, 1974
Citations
0
Influential Citations
22
Citations
Journal
Carbohydrate Research
Abstract
Abstract 2-(6-Aminohexanamido)ethyl 1-thio-β- d -galactopyranoside ( 5 ) and 1-thio-β- d -glucopyranoside ( 9 ) were prepared by the following scheme: 2,3,4,6-tetra- O -acetyl-1-thio-β- d -aldopyranoses, generated from 2- S -(2,3,4,6-tetra- O -acetyl-β- d -aldopyranosyl)-2-thiopseudourea hydrobromides, were aminoethylated with ethylenimine, followed by N -acylation of the products with 6-(trifluoroacetamido)hexanoic acid ( 1 ), and O -deacylation. These reactions could be carried out consecutively without isolation of intermediates, and the products obtained after gel chromatography were de(trifluoroacetyl)ated to obtain the final products. The chain lengths of the aglycons were further extended by repeating the acylation and the de(trifluoroacetyl)ation. An analog containing glycerol in lieu of a sugar was prepared by a similar reaction-scheme.