Issue 24, 2009
From the journal:

Organic & Biomolecular Chemistry

Syntheses of difluorinated carbasugar phosphates from trifluoroethanol†

Timo Anderl,a   Christophe Audouard,a   Afjal Miah,a   Jonathan M. Percy,*b   Giuseppe Rinaudob  and  Kuldip Singha  

* Corresponding authors

a Department of Chemistry, University of Leicester, University Road, Leicester, UK

b WestCHEM Department of Pure and Applied Chemistry, Thomas Graham Building, 295 Cathedral Street, Glasgow, UK
E-mail: jonathan.percy@strath.ac.uk
Fax: +44 141 548 4822
Tel: +44 141 548 4398

Abstract

Difluorinated cyclohexene diols (prepared from trifluoroethanol) can be elaborated to racemic analogues of phosphorylated sugarsvia regioselective protection and phosphorylation of the exposed C-1 hydroxyl group. Cis-diol protection was achieved using stannylene methodology, though the regioselectivity depended on the orientation of the methyl group at C-5. UpJohn dihydroxylation is effective with the phosphotriester in place and global deprotection to the tetrol monophosphates is efficient.

Graphical abstract: Syntheses of difluorinated carbasugar phosphates from trifluoroethanol

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Article information

DOI
https://doi.org/10.1039/B914068A
Article type
Paper
Submitted
14 Jul 2009
Accepted
21 Sep 2009
First published
20 Oct 2009

Org. Biomol. Chem., 2009,7, 5200-5206

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Syntheses of difluorinated carbasugar phosphates from trifluoroethanol

T. Anderl, C. Audouard, A. Miah, J. M. Percy, G. Rinaudo and K. Singh, Org. Biomol. Chem., 2009, 7, 5200 DOI: 10.1039/B914068A

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