In:
European Journal of Organic Chemistry, Wiley, Vol. 2007, No. 9 ( 2007-03), p. 1517-1521
Abstract:
The synthesis of hitherto unknown 1‐[3‐(hydroxymethyl)‐2‐methyl‐4‐methyleneisoxazolidin‐5‐yl]thymine ( 5 ), 1‐{( Z )‐[3‐(hydroxymethyl)‐2‐methylisoxazolidin‐4‐ylidene]methyl}thymine ( 6 ), and 1‐{( E )‐[3‐(hydroxymethyl)‐2‐methylisoxazolidin‐5‐ylidene]methyl}thymine ( 7 ) is described. The first compound can be regarded as a N,O‐analogue of Entecavir and DMDC, which contains thymine as a nucleobase. The key allenic nucleobase was prepared in good yields starting from 2,3‐dibromopropene. The subsequent 1,3‐dipolar cycloaddition proceeded with good site selectivity to give 5 and regioisomeric nucleosides 6 and 7 .(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)
Type of Medium:
Online Resource
ISSN:
1434-193X
,
1099-0690
DOI:
10.1002/ejoc.v2007:9
DOI:
10.1002/ejoc.200600817
Language:
English
Publisher:
Wiley
Publication Date:
2007
detail.hit.zdb_id:
1475010-7
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