Abstract
Oxidation of the dithioacetal groups in the O-acetylated 5-azido-5-deoxy dibenzyl dithioacetal 3 of D-xylose and that ( 7) of D-ribose leads to triazoline derivatives 4 and 8, the products of sequential oxidation to the bis(sulfones), loss of AcOH between C-1 and C-2 and, spontaneous intramolecular 1,3-dipolar cycloaddition of an azido ketene intermediate. A possible explanation of the observed diastereoselectivity is discussed.
Published Version
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