A determination of the structure of 4-(d

Add time:08/09/2019    Source:sciencedirect.com

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.

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