LITHIATION-MEDIATED C-C SILYL AND STANNYL MIGRATIONS OBSERVED IN 6-CHLORO-9-(BETA-D-RIBOFURANOSYL)PURINE

Authors
KATO K HAYAKAWA H TANAKA H KUMAMOTO H MIYASAKA T
Citation
K. Kato et al., LITHIATION-MEDIATED C-C SILYL AND STANNYL MIGRATIONS OBSERVED IN 6-CHLORO-9-(BETA-D-RIBOFURANOSYL)PURINE, Tetrahedron letters, 36(36), 1995, pp. 6507-6510
Citations number
14
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
36
Issue
36
Year of publication
1995
Pages
6507 - 6510
Database
ISI
SICI code
0040-4039(1995)36:36<6507:LCSASM>2.0.ZU;2-Z
Abstract
Lithiation of imethylsilyl)-beta-D-ribofuranosyl]-6-chloropurine (1) w ith LTMP (lithium 2,2,6,6-tetramethylpiperidide) and a subsequent reac tion with either Me(3)SiCl or Bu(3)SnCl was found to effect C-2-substi tution, as a result of ''silyl or stannyl migration'' from C-8 to C-2 position. Transformation of the resulting 2-stannyl derivative (8) to 2-substituted adenosines was also examined briefly.