Stereoselective Synthesis of Carbon-Carbon-Linked Deoxy Disaccharides

G. V. M. Sharma; Govardhan R. Cherukupalli; M. H. V. Ramana Rao; A. C. Kunwar

doi:10.1055/s-2007-983751

PAPER

Stereoselective Synthesis of Carbon-Carbon-Linked Deoxy Disaccharides

G. V. M. Sharma^a, Govardhan R. Cherukupalli*^a, M. H. V. Ramana Rao^b, A. C. Kunwar^b
^a D-211, Discovery Laboratory, Organic Chemistry Division-III, Indian Institute of Chemical Technology, Hyderabad 500007, India
Fax: +1(858)7847746; e-Mail: govardhan@scripps.edu;
^b NMR Group, Indian Institute of Chemical Technology, Hyderabad 500007, India

Abstract

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Abstract

Both C(4)-C(5)-linked furanodeoxy pyranosides and C(5)-C(6)-linked pyranodeoxy pyranosides were synthesized, from d-glucose and d-galactose, respectively. The monosaccharides impart the chirality to the newly constructed deoxy saccharides.

Key words

deoxy disaccharides - chirons - glucofuranoside - dihydroxylation - galactopyranoside

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References

Current address: The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037, USA.

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The energy minimization was carried out using Sybyl 6.8 with default Tripose force field parameters. Minimization was done first with steepest descent followed by conjugate gradient methods for a maximum of 2000 iteration each or RMS deviation of 0.005 kcal/mole whichever was earlier.

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