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Tandem Acetalation-Acetylation of Sugars and Related Derivatives with Enolacetates under Solvent-Free Conditions

Debaraj Mukherjee, Bhahwal Ali Shah, Pankaj Gupta and Subhash Chandra Taneja*

*Bioorganic Chemistry Section, Indian Institute of Integrative Medicine (CSIR), Canal Road, Jammu Tawi, India, Email: sc_tanejayahoo.co.in

D. Mukherjee, B. A. Shah, P. Gupta, S. C. Taneja, J. Org. Chem., 2007, 72, 8965-8969.

DOI: 10.1021/jo070363i (free Supporting Information)


Abstract

Molecular iodine catalyzes acetalation and acetylation of sugars with stoichiometric amounts of enol acetates under solvent-free conditions to give orthogonally protected sugar derivatives in short time and good yields. At lower temperature, it is possible to obtain the acetonide acetate as a single product whereas peracetate is the major product at higher temperature.

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Key Words

Acetonides, Acetates


ID: J42-Y2007-3630