J. Kuszmann, P. Sohår
Sep 1, 1979
Citations
0
Influential Citations
11
Citations
Journal
Carbohydrate Research
Abstract
Abstract The reaction of d -glucitol with acetone-zinc chloride gave a mixture of isopropylidene derivatives, from which the 2,3:5,6-diacetal ( 12 ) could be separated as its 1,4-dimesylate ( 13 ) or 1,4-ditosylate ( 14 ). The structure of 12 was proved by converting 14 , via the 1-mono-iodide, into the known 1-deoxy- d -glucitol, and by mass-spectrometric investigation of the 1-deoxy-4- O -methyl diacetal. The terminally situated acetal group in 12 can be selectively hydrolyzed, and, on treatment with base, the 5,6-dihydroxy derivative obtained gives a d -galactitol 4,5-epoxide derivative.