STANNYL MIGRATION FROM THE BASE TO THE SUGAR PORTION OF 1',2'-UNSATURATED URIDINE - THE FIRST EXAMPLE OF SUBSTITUTION AT THE 2'-POSITION

Authors
KUMAMOTO H SHINDOH S TANAKA H GEN E HARAGUCHI K KITTAKA A MIYASAKA T
Citation
H. Kumamoto et al., STANNYL MIGRATION FROM THE BASE TO THE SUGAR PORTION OF 1',2'-UNSATURATED URIDINE - THE FIRST EXAMPLE OF SUBSTITUTION AT THE 2'-POSITION, Tetrahedron letters, 39(22), 1998, pp. 3761-3764
Citations number
13
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
39
Issue
22
Year of publication
1998
Pages
3761 - 3764
Database
ISI
SICI code
0040-4039(1998)39:22<3761:SMFTBT>2.0.ZU;2-K
Abstract
We report that TBDMS-protected ro-pent-1-enofuranosyl)-6-(tributylstan nyl)uracil, when treated with LDA or LTMP, undergoes an anionic stanny l migration to yield the 2'-stannylated product. Optimization of the r eaction conditions has disclosed an efficient entry to compounds vario usly substituted at the 2'-position. Desilylation of these compounds c aused no further elimination, and furnished a hitherto unknown series of nucleoside analogues. (C) 1998 Elsevier Science Ltd. All rights res erved.