Efficient transformation of thymidine into 2',3'-didehydro-2',3'-dideoxy- thymidine (D4T) involving opening of a 2,3'-anhydro derivative by phenylselenol

Article abstract of DOI:10.1080/15257779508010686

A new, high-yielding method for introduction of the selenophenyl residue at the 3'- position of thymidine is reported. This reaction avoided any strongly basic or reductive reagent, thus allowing the use of benzoate ester as a protective group at O-5'. Further oxidation-elimination sequence followed by basic deprotection afforded 2',3'-didehydro-2',3'- dideoxythymidine (D4T) in 67.5% overall yield from thymidine.

Full text of DOI:10.1080/15257779508010686

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Efficient Transformation of Thymidine
into 2′,3′-Didehydro-2′,3′-Dideoxy-
Thymidine (D4T) Involving Opening
of a 2,3′-Anhydro Derivative by
Phenylselenol
Stéfan Becouarn a , Stanislas Czernecki a & Jean-Marc Valéry a
a Laboratoire de Chimie des Glucides , Université Pierre et Marie
Curie 4 Place Jussieu , Paris, 75005, France
Published online: 24 Sep 2006.
To cite this article: Stéfan Becouarn , Stanislas Czernecki & Jean-Marc Valéry (1995) Efficient
Transformation of Thymidine into 2′,3′-Didehydro-2′,3′-Dideoxy-Thymidine (D4T) Involving
Opening of a 2,3′-Anhydro Derivative by Phenylselenol, Nucleosides and Nucleotides, 14:6,
1227-1232, DOI: 10.1080/15257779508010686
To link to this article: http://dx.doi.org/10.1080/15257779508010686
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