SYNTHESIS OF L-ENANTIOMERS OF 4'-THIOARABINOFURANOSYL PYRIMIDINE NUCLEOSIDES

Authors
SATOH H YOSHIMURA Y SAKATA S MIURA S MACHIDA H MATSUDA A
Citation
H. Satoh et al., SYNTHESIS OF L-ENANTIOMERS OF 4'-THIOARABINOFURANOSYL PYRIMIDINE NUCLEOSIDES, Bioorganic & medicinal chemistry letters, 8(9), 1998, pp. 989-992
Citations number
18
Categorie Soggetti
Chemistry Inorganic & Nuclear","Chemistry Medicinal
Journal title
Bioorganic & medicinal chemistry letters → ACNP
ISSN journal
0960894X
Volume
8
Issue
9
Year of publication
1998
Pages
989 - 992
Database
ISI
SICI code
0960-894X(1998)8:9<989:SOLO4P>2.0.ZU;2-5
Abstract
L-Enantiomers of 4'-thioarabinofuranosyl pyrimidine nucleosides were s ynthesized from D-xylose. Methyl 2,3,5-tri-O-benzyl-D-xylofuranoside 6 was converted to the corresponding xylitol 7, which was treated with MsCl and then Na2S to give 1,4-anhydro-L-4-thioarabitol 8. As previous ly reported, Pummerer rearrangement of 8 followed by glycosylation wit h a silylated thymine and N4-acetylcytosine derivative and deprotectio n gave the corresponding alpha- and beta-L-4'-thioarabinofuranosyl pyr imidine nucleosides, (C) 1998 Elsevier Science Ltd. All rights reserve d.