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  • Title: Regio- and stereocontrolled selective debenzylation and substitution reactions of C-2 formyl glycals. Application in the synthesis of constrained beta-sugar amino acids.
    Author: Rawal GK, Rani S, Kumari N, Vankar YD.
    Journal: J Org Chem; 2009 Aug 07; 74(15):5349-55. PubMed ID: 19534480.
    Abstract:
    O-Benzyl-protected C-2 formyl glycals are regioselectively deprotected and acetylated first at C-3 and then at C-6 upon treatment with a ZnCl2-Ac2O-AcOH reagent combination. Treatment of the thus-obtained C-3 acetate with various nucleophiles leads to substitution at C-3 with retention of stereochemistry in the galactal series, whereas mixed results were obtained with glucal-derived compounds. Two of the azido-substituted products were converted into the corresponding beta-sugar amino acids.
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