Synthesis of novel chiral compounds of purine and pyrimidine bases

Authors
Citation
Yh. Wang et Qh. Chen, Synthesis of novel chiral compounds of purine and pyrimidine bases, SCI CHINA B, 42(2), 1999, pp. 121-130
Citations number
15
Categorie Soggetti
Chemistry
Journal title
SCIENCE IN CHINA SERIES B-CHEMISTRY
ISSN journal
1001652X → ACNP
Volume
42
Issue
2
Year of publication
1999
Pages
121 - 130
Database
ISI
SICI code
1001-652X(199904)42:2<121:SONCCO>2.0.ZU;2-G
Abstract
The physiologically active groups such as purine and pyrimidine bases are i ntroduced to the asymmetric synthesis. The optically pure compounds bearing purine and pyrimidine bases (5a-5e) were prepared via the asymmetric Micha el addition reaction of purines and pyrimidines as Michael donators with th e chiral source 5-(R)-[(1R, 2S, 5R)-menthyloxy]-2(5H)-furanone (3a), which was prepared from the natural chiral auxiliary(-)-menthol. The synthetic me thod was studied in derail and the new compounds were identified on the bas is of their analytical data and spectroscopic data, such as [alpha](D)(20), IR, UV, H-1 NMR, C-13 NMR and MS. The absolute configuration of 5a was est ablished by X-ray crystallography. The results provided an efficient synthe tic route to chiral purines and pyrimidine analogues, and offered chiral so urces for further research on the physiologically active compounds of chira l nucleotides.