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2-C-trifluoromethyl substituted pentoses

2-C-trifluoromethyl substituted pentoses
2-C-trifluoromethyl substituted pentoses
The synthesis of racemic 2-C-trifluoromethyl ribose and racemic 2-C-trifluoromethyl arabinose is described. The four step reaction sequence includes diastereoselective enol ether addition to methyl trifluoropyruvate, diastereoselective dihydroxylation of the CC double bond with potassium osmate, lactonization, and finally SMEAH reduction to give the lactol. 2-C-Trifluoromethyl pentoses exhibit unexpected anomeric and tautomeric stabilities.
0040-4020
14023-14030
Logothetis, Thomas A.
9f42a28f-0c36-4d47-a137-7a317acb0237
Eilitz, Uwe
a0fba914-1eb2-4326-b6bc-902812823648
Hiller, Wolfgang
577b3a25-1a99-4dee-b8ed-e6418fdf30d2
Burger, Klaus
1924768d-b77c-43b7-bfae-a3f8c7682507
Logothetis, Thomas A.
9f42a28f-0c36-4d47-a137-7a317acb0237
Eilitz, Uwe
a0fba914-1eb2-4326-b6bc-902812823648
Hiller, Wolfgang
577b3a25-1a99-4dee-b8ed-e6418fdf30d2
Burger, Klaus
1924768d-b77c-43b7-bfae-a3f8c7682507

Logothetis, Thomas A., Eilitz, Uwe, Hiller, Wolfgang and Burger, Klaus (1998) 2-C-trifluoromethyl substituted pentoses. Tetrahedron, 54 (46), 14023-14030. (doi:10.1016/S0040-4020(98)00866-7).

Record type: Article

Abstract

The synthesis of racemic 2-C-trifluoromethyl ribose and racemic 2-C-trifluoromethyl arabinose is described. The four step reaction sequence includes diastereoselective enol ether addition to methyl trifluoropyruvate, diastereoselective dihydroxylation of the CC double bond with potassium osmate, lactonization, and finally SMEAH reduction to give the lactol. 2-C-Trifluoromethyl pentoses exhibit unexpected anomeric and tautomeric stabilities.

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e-pub ahead of print date: 12 November 1998
Organisations: Chemistry
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Identifiers

Local EPrints ID: 360744
URI: http://eprints.soton.ac.uk/id/eprint/360744
DOI: doi:10.1016/S0040-4020(98)00866-7
ISSN: 0040-4020
PURE UUID: a127ebc0-4818-48ce-a9be-d6f8cdf37601
ORCID for Thomas A. Logothetis: ORCID iD orcid.org/0000-0002-3437-5287

Catalogue record

Date deposited: 03 Jan 2014 16:23
Last modified: 15 Mar 2024 03:30

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Contributors

Author: Thomas A. Logothetis ORCID iD
Author: Uwe Eilitz
Author: Wolfgang Hiller
Author: Klaus Burger

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