Martin Avalos Gonzalez, J. F. Mota, I. G. Monterrey
Oct 15, 1986
Citations
1
Influential Citations
23
Citations
Journal
Carbohydrate Research
Abstract
Abstract 1,3,4,6-Tetra- O -acetyl-2-deoxy-2-isothiocyanato-α- d -glucopyranose, produced from 1,3,4,6-tetra- O -acetyl-2-amino-2-deoxy-α- d -glucopyranose hydrochloride, thiophosgene, and calcium carbonate, was condensed with alkyl- and aryl-amines in ether to afford the crystalline 1,3,4,6-tetra- O -acetyl-2-[3-alkyl(aryl)-thioureido]-2-deoxy-α- d -glucopyranoses ( 2 ). Compounds 2 and the β anomers 3 were converted in high yield into 2-alkyl(aryl)amino-(3,4,6-tri- O -acetyl-1,2-dideoxy-α- d -glucopyrano)[2,1- d ]-2-thiazoline hydrobromides ( 4 ) by hydrogen bromide-promoted cyclisation. The O -deacetylated thiazoline hydrobromide 5 was also isolated and converted into 2-[ N -(4-methoxyphenyl)acetamido]-(3,4,6-tri- O -acetyl-1,2-dideoxy-α- d -glucopyrano)[2,1- d ]-2-thiazoline ( 8 ). Conformational studies of 4 and 8 were made by 1 H-n.m.r. spectroscopy.