W. J. Humphlett
1968
Citations
0
Influential Citations
3
Citations
Journal
Carbohydrate Research
Abstract
Abstract The structure of 4-( d - arabino -tetrahydroxybutyl)-4-thiazoline-2-thione ( 1 ) was determined by means of synthesis, and was in agreement with the recent structural assignment by Jochims . Procedures of carbohydrate chemistry afforded typical derivatives of 1 , and provided a total synthesis from d -glucose. The heterocyclic ring of 1 gave reactions characteristic of and forms of a 4-thiazoline-2-thione. Periodate oxidation of 1 provided a route to the lowest homolog 11 , which was alternatively prepared by a known method from the appropriate α-chloroketone and ammonium dithiocarbamate. An unequivocal preparation by a similar reaction with 3,4,5,6-tetra- O -acetyl-1-bromo-1-deoxy- d - arabino -hexulose led to 1 . The formation of carbohydrate-derived 4-thiazoline-2-thiones appears to be a general reaction of α-halo ketoses with ammonium dithiocarbamate.