A protected form of (1S,2R,3S,4R)-4-aminocyclopentane-1,2,3-triol, a useful precursor to 5′-nor carbocyclic nucleosides

被引:5
|
作者
Rajappan, VP [1 ]
Hegde, VR [1 ]
Schneller, SW [1 ]
机构
[1] Auburn Univ, Dept Chem, Auburn, AL 36849 USA
关键词
D O I
10.1081/SCC-100105336
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
5'-Nor carbocyclic nucleosides have been found to possess a variety of meaningful biological properties. One of the building blocks for this class of compounds is (1S,2R,3S,4R)-4-aminocyclopentane-1,2,3-triol. To date, the reported routes to this compound are not particularly facile. Thus, a convenient route to this triol in its protected isopropylidene form (2) from (+)-(1R,4S)-4-hydroxy-2-cyclopenten-1-yl acetate. This will facilitate the preparation of new 5'-nor carbocyclic nucleosides in the "D-ribo-like" configuration. This method is also adaptable to the "L-like" series and the 2'- and 3'-deoxy analogs.
引用
收藏
页码:2849 / 2854
页数:6
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