4′-Methyloxycarbamyl-3′-deoxy-5-methyluridine; synthesis of a novel nucleoside analogue

4′-Methyloxycarbamyl-3′-deoxy-5-methyluridine; synthesis of a novel nucleoside analogue

The preparation of 4′-methyloxycarbamyl-3′-deoxythymidine from chiral amino acid precursors is described. The route chosen employs a hitherto unreported electrochemical oxidation of a suitably protected derivative of trans-4-hydroxy-L-proline, to obtain the key intermediate compound. Conventional co...

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Bibliographic Details
Published in:Tetrahedron Vol. 51; no. 9; pp. 2719 - 2728
Main Authors: Pickering, Lea, Malhi, Baljinder S, Coe, Paul L, Walker, Richard T
Format: Journal Article
Language:English
Published: Elsevier Ltd 27-02-1995
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Description
Summary:The preparation of 4′-methyloxycarbamyl-3′-deoxythymidine from chiral amino acid precursors is described. The route chosen employs a hitherto unreported electrochemical oxidation of a suitably protected derivative of trans-4-hydroxy-L-proline, to obtain the key intermediate compound. Conventional condensation methodology is then used to arrive at the target nucleoside The preparation of 4′-methyloxycarbamyl-3′-deoxy-5-methyluridine ( 3) from α-methoxypyrrolidine ( 2), obtained via anodic oxidation of a derivative of trans-4-hydroxy-proline ( 1), is described.
ISSN:0040-4020
1464-5416
DOI:10.1016/0040-4020(95)00020-9