ChemInform Abstract: 2‐O‐Benzylation in D‐Gluconamide Derivative under Basic Conditions with Complete Retention of Stereo‐Integrity: Convenient Access to 2‐O‐Benzyl‐3,4:5,6‐di‐O‐isopropylidene‐D‐glucitol and Other Differently Protected D‐Glucitol Derivatives.

Abstract

tives. -The search for an alternative procedure for the synthesis of chiral building block (VIIg) results in an efficient general synthesis of compounds of type (VII) on multigram scale. This approach starts with gluconate (II), conveniently available in a single step from D-gluconolactone (I). Reacting (II) with morpholine (III) affords the hitherto unknown α-hydroxy morpholine amide (IV) as a solid. The convenience in using NaBH4 for the reduction of (VI) offers a significant advantage to this alternative procedure for (VIIg).