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

被引：23

作者：

JEONG, LS

NICKLAUS, MC

GEORGE, C

MARQUEZ, VE

机构：

[1] NCI,DIV CANC TREATMENT,DEV THERAPEUT PROGRAM,MED CHEM LAB,BETHESDA,MD 20892

[2] USN,RES LAB,STRUCT MATTER LAB,WASHINGTON,DC 20375

来源：

TETRAHEDRON LETTERS | 1994年 / 35卷 / 41期

关键词：

D O I：

10.1016/S0040-4039(00)78346-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Attempted fluorination of 1-(5-O-trityl-3-deoxy-4-thio-beta-D-erythro-pentofuranosyl)-3-(2-methoxyethoxymethyl)uracil (12) and 1-(5-O-trityl-2-deoxy-4-thio-beta-D-erythro-pentofuranosyl)-3-(2-methoxyethoxymethyl) uracil (14) with diethylaminosulfur trifluoride (DAST) produced very reactive 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.

引用

页码：7573 / 7576

页数：4

共 8 条

[1] PREPARATION OF 2,3'-ANHYDROPYRIMIDINE NUCLEOSIDES USING N,N-DIETHYLAMINOSULFUR TRIFLUORIDE (DAST) [J].