Cyanohydrin Derivative of Sucrose via 3-Ketosucrose

Abstract

The cyanohydrine of 3‐ketosucrose can be obtained in good yields and with high regioselectivity. The stereoselectivity is 90 % for the isomer with axial orientation of the cyano group. By this reaction route a sucrose derivative with CC bonding of the substituent can be obtained in two steps without protecting groups in aqueous media. By its hydrolysis 3‐cyanoglucose is accessible.

Stereoselective Protection-Free Modification of 3-Keto-saccharides

“…7 Next, on the basis of the reasoning that small nucleophiles and reagents add to the bottom face, the gluco-configured derivative of 9 was prepared from 1 with the small nucleophile sodium cyanide. 26 A diastereomeric mixture (1:3.7 allo/gluco) in a total yield of 74%, with gluco-cyanohydrin 15 being the major product, was obtained (Scheme 5b). The diastereoisomers could be separated, and a pure fraction of 15 was hydrogenated, yielding the aminomethyl-branched glucoside 16.…”