Rearrangement of allylic azide and phenylthio groups of 3′-azido- or 3′-phenylthio-4′,5′-didehydro-5′-deoxyarabinofuranosyluridines

被引:21
|
作者
Takasu, H
Tsuji, Y
Sajiki, H
Hirota, K
机构
[1] Gifu Pharmaceut Univ, Med Chem Lab, Gifu 5028585, Japan
[2] Otsuka Pharmaceut Co Ltd, Med Chem Res Inst, Tokushima 7710192, Japan
关键词
nucleosides; signiatropic rearrangement; radical chain mechanism; azido group; phenylthio group;
D O I
10.1016/j.tet.2005.08.092
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The reversible intramolecular [3,3]-sigmatropic rearrangement between 1-(3-azido-3,5-dideoxy-beta-D-threo-pent-4-enofuranosyl) uracil (3) and 1-(5-azido-3,5-dideoxy-beta-D-glycero-pent-4-enofuranosyl)uraciI (4) and irreversible radical rearrangement of 1-(3,5-dideoxy-3-phenylthio-beta-threo-pent-4-enofuranosyl)uracil (5) and 1-[3,5-dideoxy-3-(4-tolyl)thio-beta-D-threo-pent-4-enofuranosyl]uracil (7) into 1-(3,5-dideoxy-5-phenylthio-beta-L-glycero-pent-4-enofuranosyl)uracil (6) and 1-[3,5-dideoxy-5-(4-tolyl)thio-beta-L-glycero-pent-3-enofuranosyl]uracil (8) were attained at room temperature. (c) 2005 Elsevier Ltd. All rights reserved.
引用
收藏
页码:11027 / 11031
页数:5
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