DEPROTECTION OF SILYL ETHERS USING 2,3-DICHLORO-5,6-DICYANO-P-BENZOQUINONE

被引:77
作者
TANEMURA, K [1 ]
SUZUKI, T [1 ]
HORAGUCHI, T [1 ]
机构
[1] NIIGATA UNIV,FAC SCI,DEPT CHEM,NIIGATA 95021,JAPAN
来源
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1992年 / 22期
关键词
D O I
10.1039/p19920002997
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
In the presence of a catalytic amount of 2,3-dichloro-5,6-dicyano-p-benzoquinone (DDQ), triethylsilyl (TES) and tert-butyldimethylsilyl (TBDMS) ethers are readily hydrolysed to the corresponding alcohols in MeCN-H2O (9:1) or tetrahydrofuran (THF)-H2O (9:1). TES ethers are cleaved to alcohols more easily than TBDMS ethers. tert-Butyldiphenylsilyl (TBDPS) ethers are stable under these reaction conditions.
引用
收藏
页码:2997 / 2998
页数:2
相关论文
共 15 条
[1]  
Adkins H., 1931, J AM CHEM SOC, V53, P1095
[2]  
Colvin E. W., 1981, SILICON ORGANIC SYNT
[3]   NEW SYNTHETIC APPROACH TO PROSTANOIDS VIA CYCLOPENTENE VINYLATION [J].
COREY, EJ ;
RAVINDRANATHAN, T .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1972, 94 (11) :4013-+
[4]   REDUCTIVE CLEAVAGE OF TERT-BUTYLDIMETHYLSILYL ETHERS BY DIISOBUTYLALUMINUM HYDRIDE [J].
COREY, EJ ;
JONES, GB .
JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (03) :1028-1029
[5]   TETRAFLUOROSILANE IS A MILD AND VERY SELECTIVE REAGENT FOR THE CLEAVAGE OF SILYL-PROTECTED ALCOHOLS [J].
COREY, EJ ;
YI, KY .
TETRAHEDRON LETTERS, 1992, 33 (17) :2289-2290
[6]   PROTECTION OF HYDROXYL GROUPS AS TERT-BUTYLDIMETHYLSILYL DERIVATIVES [J].
COREY, EJ ;
VENKATESWARLU, A .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1972, 94 (17) :6190-+
[7]   TOTAL SYNTHESIS OF (+/-)-FUMAGILLIN [J].
COREY, EJ ;
SNIDER, BB .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1972, 94 (07) :2549-&
[8]  
GREENE TW, 1981, PROTECTIVE GROUPS OR
[9]   PREPARATION AND SYNTHETIC UTILITY OF TERT-BUTYLDIPHENYLSILYL ETHERS [J].
HANESSIAN, S ;
LAVALLEE, P .
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1975, 53 (19) :2975-2977
[10]  
HAYAMI JI, 1968, TETRAHEDRON LETT, P1385