AN EFFICIENT AND HIGHLY STEREOSELECTIVE SYNTHESIS OF NUCLEOSIDE DERIVATIVES FROM FURANOID 1,2-DIOLS

Authors
ROBLES R RODRIGUEZ C IZQUIERDO I PLAZA MT MOTA A
Citation
R. Robles et al., AN EFFICIENT AND HIGHLY STEREOSELECTIVE SYNTHESIS OF NUCLEOSIDE DERIVATIVES FROM FURANOID 1,2-DIOLS, Tetrahedron : asymmetry, 8(17), 1997, pp. 2959-2965
Citations number
17
Categorie Soggetti
Chemistry Inorganic & Nuclear","Chemistry Inorganic & Nuclear","Chemistry Physical
Journal title
Tetrahedron : asymmetry → ACNP
ISSN journal
09574166
Volume
8
Issue
17
Year of publication
1997
Pages
2959 - 2965
Database
ISI
SICI code
0957-4166(1997)8:17<2959:AEAHSS>2.0.ZU;2-X
Abstract
Reaction between suitably protected furanoid glycals 1b-4b, readily ob tained from furanoid 1,2-diols (1a-4a), and different silylated pyrimi dine bases, gave the corresponding 3',5'- and 3',5',6'-O-protected 2'- deoxy-2'-iodo-beta-D-xylo-pentofuranosyl 5-10 and beta-D-gluco-hexofur anosyl 11 nucleosides, respectively. Compound 5 has been transformed i nto its 2'-deoxy 12 and 2',3'-anhydro 14 derivatives. The high stereos electivity of the reaction is discussed. (C) 1997 Elsevier Science Ltd .