A simple stereoselective synthesis of biologically important 2-halo-2,3-dideoxy-arabinose derivatives from 1,1,1,2-tetrafluoroethane (134a) and 1-chloro-2,2,2-trifluoroethane (133a)

A simple stereoselective synthesis of biologically important 2-halo-2,3-dideoxy-arabinose derivatives from 1,1,1,2-tetrafluoroethane (134a) and 1-chloro-2,2,2-trifluoroethane (133a)

A simple stereoselective three step synthesis of 2-fluoro- and 2-chloro-2,3-dideoxy arabinose derivatives from the readily available starting materials, ( R)-glycidol and either 1,1,1,2-tetrafluoroethane (134a) or 1-chloro-2,2,2-trifluroethane (133a), is described. This compares very favourably with...

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Bibliographic Details
Published in:Journal of fluorine chemistry Vol. 102; no. 1; pp. 43 - 50
Main Authors: Coe, Paul L., Burdon, James, Haslock, Iain B.
Format: Journal Article
Language:English
Published: Elsevier B.V 01-03-2000
Subjects:
De-novo synthesis
Stereospecific
Sugar analogues
Trifluorovinyllithium
Sugar analogues
De-novo synthesis
Stereospecific
Trifluorovinyllithium
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Description
Summary:A simple stereoselective three step synthesis of 2-fluoro- and 2-chloro-2,3-dideoxy arabinose derivatives from the readily available starting materials, ( R)-glycidol and either 1,1,1,2-tetrafluoroethane (134a) or 1-chloro-2,2,2-trifluroethane (133a), is described. This compares very favourably with the multistep syntheses previously described in the literature. A mechanistic interpretation of the reaction via an unfavourable 5-endo-trig cyclisation is given.
ISSN:0022-1139
1873-3328
DOI:10.1016/S0022-1139(99)00241-9