A STEREOSELECTIVE SYNTHESIS OF ALPHA-2'-DEOXY-2-THIOURIDINE AND BETA 2'-DEOXY-2-THIOURIDINE

Authors
KUIMELIS RG HOPE H NAMBIAR KP
Citation
Rg. Kuimelis et al., A STEREOSELECTIVE SYNTHESIS OF ALPHA-2'-DEOXY-2-THIOURIDINE AND BETA 2'-DEOXY-2-THIOURIDINE, Nucleosides & nucleotides, 12(7), 1993, pp. 737-755
Citations number
49
Categorie Soggetti
Biology
Journal title
Nucleosides & nucleotides → ACNP
ISSN journal
07328311
Volume
12
Issue
7
Year of publication
1993
Pages
737 - 755
Database
ISI
SICI code
0732-8311(1993)12:7<737:ASSOAA>2.0.ZU;2-M
Abstract
A stereoselective glycosylation procedure is described for the synthes is of protected alpha- and beta-2'-deoxy-2-thiouridine (dS2U) in 68% a nd 94% yield, respectively. Evidence is presented that suggests the re action proceeds through a silylated thioglycoside intermediate. This i ntermediate undergoes an efficient S2-->N1 rearrangement mediated by S nCl4. The phosphoramidite and phosphodiester synthons and a dS2U dinuc leotide are also synthesized and the X-ray structure of beta-dS2U is p resented.