Regio- and stereocontrolled selective debenzylation and substitution reactions of C-2 formyl glycals. Application in the synthesis of constrained beta-sugar amino acids

Girish K Rawal; Shikha Rani; Nitee Kumari; Yashwant D Vankar

doi:10.1021/jo9008222

Regio- and stereocontrolled selective debenzylation and substitution reactions of C-2 formyl glycals. Application in the synthesis of constrained beta-sugar amino acids

J Org Chem. 2009 Aug 7;74(15):5349-55. doi: 10.1021/jo9008222.

Authors

Girish K Rawal¹, Shikha Rani, Nitee Kumari, Yashwant D Vankar

Affiliation

¹ Department of Chemistry, Indian Institute of Technology, Kanpur 208016, India.

PMID: 19534480
DOI: 10.1021/jo9008222

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.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Amino Acids / chemical synthesis*
Amino Acids / chemistry
Carbohydrates / chemical synthesis*
Carbohydrates / chemistry
Glycosides / chemistry*
Molecular Conformation
Stereoisomerism

Substances

Amino Acids
Carbohydrates
Glycosides