Synthesis of 2-iodoglycals, glycals, and 1,1′-disaccharides from 2-deoxy-2-iodopyranoses under dehydrative glycosylation conditions

Identifier:  imarina:5631893

Handle: https://hdl.handle.net/20.500.11797/imarina5631893

Authors:  Rodriguez, Miguel Angel; Boutureira, Omar; Matheu, M Isabel; Diaz, Yolanda; Castillon, Sergio; Seeberger, Peter H

Abstract:
(Chemical Equation Presented) Treatment of 2-deoxy-2-iodopyranoses under dehydrative glycosylation conditions afforded pyranose glycals, 2-iodoglycals, and 1,1′-disaccharides instead of the expected glycoside products. While the product distribution revealed that this reaction is very sensitive to the configuration of the 2-deoxy-2-iodopyranose, 2-iodopyranoid glycals can be obtained almost exclusively in good yields by employing 3,4-O-isopropylidene as a cyclic bifunctional protecting group. The behavior of 2-deoxy-2-iodopyranoses during the dehydrative elimination reaction has been analyzed in detail. © 2007 American Chemical Society.