Stereoselective synthesis of C-4 '-aminouridines (uracil C-4-amino-D-ribonucleosides)

Authors
Yokoyama, M Ikenogami, T Togo, H
Citation
M. Yokoyama et al., Stereoselective synthesis of C-4 '-aminouridines (uracil C-4-amino-D-ribonucleosides), J CHEM S P1, (13), 2000, pp. 2067-2071
Citations number
22
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1
ISSN journal
14704358 → ACNP
Issue
13
Year of publication
2000
Pages
2067 - 2071
Database
ISI
SICI code
1470-4358(2000):13<2067:SSOC'(>2.0.ZU;2-F
Abstract
The first C-4'-aminouridines can be synthesized in an alpha,beta-stereosele ctive manner starting from L-glutamic acid. For the synthesis of alpha-C-4' -aminouridine, a key compound 9 is cyclized with trifluoroacetic acid follo wed by reduction with NaBH3CN, while 9 is reduced with NaBH4 followed by me sylation to give beta-C-4'-aminouridine. Further, an acetonide-protection m ethod is preferred for the synthesis of alpha-C-4'-aminouridine.