Synthesis and applications of a fluorous THP protective group

被引:54
作者
Wipf, P [1 ]
Reeves, JT [1 ]
机构
[1] Univ Pittsburgh, Dept Chem, Pittsburgh, PA 15260 USA
关键词
D O I
10.1016/S0040-4039(99)00866-7
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A recyclable fluorous labeled THP protecting group has been developed that allows for simple purification of small molecules by liquid-liquid extraction with FC-72/MeCN, and of larger or more polar molecules by solid phase extraction with fluorous reverse phase silica gel. In addition, we report a new glycosylation method which uses the Cp2ZrCl2-AgClO4 reagent system to activate an anomeric sulfoxide. (C) 1999 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:4649 / 4652
页数:4
相关论文
共 20 条
[1]   RETENTION AND SELECTIVITY CHARACTERISTICS OF A NONPOLAR PERFLUORINATED STATIONARY PHASE FOR LIQUID-CHROMATOGRAPHY [J].
BILLIET, HAH ;
SCHOENMAKERS, PJ ;
DEGALAN, L .
JOURNAL OF CHROMATOGRAPHY, 1981, 218 (1-3) :443-454
[2]   STUDY OF THE ALKYLATION OF CHLOROSILANES .1. SYNTHESIS OF TETRA(1H,1H,2H,2H-POLYFLUOROALKYL)SILANES [J].
BOUTEVIN, B ;
GUIDAPIETRASANTA, F ;
RATSIMIHETY, A ;
CAPORICCIO, G ;
GORNOWICZ, G .
JOURNAL OF FLUORINE CHEMISTRY, 1993, 60 (2-3) :211-223
[3]   A NEW ADDITION OF FLUOROALKYL IODIDES TO ALKENES CATALYZED BY RANEY-NICKEL [J].
CHEN, QY ;
YANG, ZY .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1986, (07) :498-499
[4]   Thermal allylations of aldehydes with a fluorous allylstannane. Separation of organic and fluorous products by solid phase extraction with fluorous reverse phase silica gel [J].
Curran, DP ;
Hadida, S ;
He, M .
JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (20) :6714-6715
[5]  
Curran DP, 1998, ANGEW CHEM INT EDIT, V37, P1175, DOI 10.1002/(SICI)1521-3773(19980518)37:9<1174::AID-ANIE1174>3.0.CO
[6]  
2-P
[7]   Fluorous biphase chemistry [J].
Horváth, IT .
ACCOUNTS OF CHEMICAL RESEARCH, 1998, 31 (10) :641-650
[8]   QUANTITATIVE DEALKYLATION OF ALKYL ETHERS VIA TREATMENT WITH TRIMETHYLSILYL IODIDE - NEW METHOD FOR ETHER HYDROLYSIS [J].
JUNG, ME ;
LYSTER, MA .
JOURNAL OF ORGANIC CHEMISTRY, 1977, 42 (23) :3761-3764
[9]  
Kainz S, 1998, SYNTHESIS-STUTTGART, P1425
[10]  
Kocienski P.J., 1994, PROTECTING GROUPS