Epimerization of carbohydrates via stannylene acetals. A practical synthesis of D-Talose

Article abstract of DOI:10.1080/07328309808002337

When treated with Bu₂SnO in a suitable solvent, reducing sugars preferentially form 1,2-O-stannylene acetals and, on prolonged treatment with a slight excess of the reagent at reflux temperature, they undergo epimerization. This allows simple preparation of rare monosaccharides from readily available, unprotected starting materials. The process is equilibrium driven, and the equilibrium is shifted largely in favor of structures having an axial hydroxyl group at position 2.

Full text of DOI:10.1080/07328309808002337

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Journal of Carbohydrate Chemistry
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Epimerization of Carbohydrates via
Stannylene Acetals. A Practical Synthesis
of D-Talose
a
a
György Hodosi & Pavol Kováč
a
NIDDK , National Institutes of Health , Bethesda, MD, 20892-0815,
U.S.A.
Published online: 22 Aug 2006.
To cite this article: György Hodosi & Pavol Kováč (1998) Epimerization of Carbohydrates via
Stannylene Acetals. A Practical Synthesis of D-Talose , Journal of Carbohydrate Chemistry, 17:4-5,
557-565
To link to this article: http://dx.doi.org/10.1080/07328309808002337
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