FACILE FLUORINATION OF DEOXY-4'-THIOPYRIMIDINE NUCLEOSIDES WITH DOWN HYDROXYL-GROUPS - RETENTION OF CONFIGURATION AFTER FLUORIDE OPENING OFTHE QUATERNIZED N-3-MEM ANHYDRONUCLEOSIDES

Authors
JEONG LS NICKLAUS MC GEORGE C MARQUEZ VE
Citation
Ls. Jeong et al., FACILE FLUORINATION OF DEOXY-4'-THIOPYRIMIDINE NUCLEOSIDES WITH DOWN HYDROXYL-GROUPS - RETENTION OF CONFIGURATION AFTER FLUORIDE OPENING OFTHE QUATERNIZED N-3-MEM ANHYDRONUCLEOSIDES, Tetrahedron letters, 35(41), 1994, pp. 7573-7576
Citations number
8
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
35
Issue
41
Year of publication
1994
Pages
7573 - 7576
Database
ISI
SICI code
0040-4039(1994)35:41<7573:FFODNW>2.0.ZU;2-0
Abstract
Attempted fluorination of ro-pentofuranosyl)-3-(2-methoxyethoxymethyl) uracil (12) and -erythro-pentofuranosyl)-3-(2-methoxyethoxymethyl) ura cil (14) with diethylaminosulfur trifluoride (DAST) produced very reac tive N-3-MEM-O-2,2- and N-3-MEM-O-2,3-anhydronucleoside intermediates (16) that reacted with KF to give the desired fluorinated nucleosides with retention of configuration.