Issue 9, 1991
From the journal:

Journal of the Chemical Society, Perkin Transactions 1

Diastereoselective free-radical reactions. Part 2. Synthesis of 2-deoxy-β-C-pyranosides by diastereoselective hydrogen-atom transfer

David Crich  and  Linda B. L. Lim  

Abstract

C-Glycosides of 2,3-dideoxy-arabino-heptulosonate esters are prepared from the corresponding 2,3dideoxy-1-phenylsulphonyl derivatives by reductive desulphonylation with lithium naphthalenide and quenching of the so-formed enolate with appropriate alkyl halides. These C-glycosides are saponified and decarboxylated by the Barton O-acyl thiohydroxamate protocol to give 2-deoxy-β-C-glycosides with very high diastereoselectivities.

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Article information

DOI
https://doi.org/10.1039/P19910002205
Article type
Paper

J. Chem. Soc., Perkin Trans. 1, 1991, 2205-2208

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Diastereoselective free-radical reactions. Part 2. Synthesis of 2-deoxy-β-C-pyranosides by diastereoselective hydrogen-atom transfer

D. Crich and L. B. L. Lim, J. Chem. Soc., Perkin Trans. 1, 1991, 2205 DOI: 10.1039/P19910002205

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