Synthesis and Rearrangement of 3′-α-Diethylphosphono-3′-β- O-methanesulfonyluridines

Tracy J Baker; David F Wiemer

doi:10.1016/S0040-4020(00)00198-8

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Synthesis and Rearrangement of 3′-α-Diethylphosphono-3′-β- O-methanesulfonyluridines

Journal article

Peer reviewed

Synthesis and Rearrangement of 3′-α-Diethylphosphono-3′-β- O-methanesulfonyluridines

Tracy J Baker and David F Wiemer

Tetrahedron, Vol.56(20), pp.3127-3131

2000

DOI: 10.1016/S0040-4020(00)00198-8

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Abstract

Preparation of a uridine derivative bearing both diethylphosphono and methanesulfonate substituents at the 3′-position has been accomplished by reaction of the corresponding α-hydroxy phosphonate with methanesulfinyl chloride and subsequent oxidation. While this methanesulfonate did not undergo elimination under standard reaction conditions, treatment with TBAF results in a novel rearrangement leading to the corresponding 2′-phosphate.

nucleosides

nucleotides

phosphonic acids and derivatives

phosphoric acids and derivatives

rearrangements

Details

Title: Subtitle: Synthesis and Rearrangement of 3′-α-Diethylphosphono-3′-β- O-methanesulfonyluridines
Creators: Tracy J Baker
David F Wiemer
Resource Type: Journal article
Publication Details: Tetrahedron, Vol.56(20), pp.3127-3131
Publisher: Elsevier Ltd
DOI: 10.1016/S0040-4020(00)00198-8
ISSN: 0040-4020
eISSN: 1464-5416
Language: English
Date published: 2000
Academic Unit: Chemistry; Neuroscience and Pharmacology
Record Identifier: 9983985937202771

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