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Synlett 2012(4): 541-544  
DOI: 10.1055/s-0031-1290327
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

Organocatalytic Conversion of Ribose and Other Protected Carbohydrate Derivatives into 2-Deoxy-lactones

Sebastian Wendeborn*, Régis Mondière, Isabelle Keller, Hannes Nussbaumer
Syngenta Crop Protection AG, Werk Stein, Schaffhauserstr., 4332 Stein, Switzerland
Fax: +41(62)8660860; e-Mail: sebastian.wendeborn@syngenta.com;
Further Information

Publication History

Received 31 October 2011
Publication Date:
27 January 2012 (online)

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Abstract

We report the simultaneous reduction of the 2-position and oxidation of the anomeric position in several protected furanosyl and pyranosyl sugar derivatives, mediated through NHC catalysis. This reaction allows the one-step access to highly valuable 2-deoxy-sugars from abundant 2-oxygenated sugar derivatives.

Key words

carbenes - deoxygenation - green chemistry - isomerization - umpolung

    References and Notes

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    Spectroscopic Data for Compound 17
    ¹H NMR (400 MHz, DMSO-d 6): δ = 2.22 (dd, J = 17.61, 2.20 Hz, 1 H), 2.81 (dd, J = 17.79, 6.42 Hz, 1 H), 3.47-3.62 (m, 2 H), 4.21-4.32 (m, 2 H), 5.06 (t, J = 5.50 Hz, 1 H), 5.49 (d, J = 4.03 Hz, 1 H).

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