A catalytic amount of nickel(II) chloride hexahydrate and 1,2-ethanedithiol is a good combination for the cleavage of tetrahydropyranyl (THP) and tert-butyldimethylsilyl (TBS) ethers

被引:32
作者
Khan, AT [1 ]
Islam, S
Choudhury, LH
Ghosh, S
机构
[1] Indian Inst Technol, Dept Chem, Gauhati 781039, India
[2] Visva Bharati Univ, Dept Chem, Santini Ketan 731235, W Bengal, India
关键词
deprotection of TBS and THP ethers;
D O I
10.1016/j.tetlet.2004.11.011
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Various THP and TBS ethers can be unmasked easily to the corresponding hydroxyl compounds in good yields by using a combination of a catalytic amount of nickel(II) chloride hexahydrate and 1,2-ethanedithiol at room temperature. In addition, alkyl TBS ethers can be hydrolyzed chemo selectively in the presence of aryl TBS ethers. Moreover, alkyl TBS ethers can be cleaved easily in the presence of alkyl or aryl THP ethers using the same conditions. (C) 2004 Published by Elsevier Ltd.
引用
收藏
页码:9617 / 9621
页数:5
相关论文
共 14 条
[1]   PROTECTION OF HYDROXYL GROUPS AS TERT-BUTYLDIMETHYLSILYL DERIVATIVES [J].
COREY, EJ ;
VENKATESWARLU, A .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1972, 94 (17) :6190-+
[2]   Selective monodeprotection of bis-silyl ethers [J].
Crouch, RD .
TETRAHEDRON, 2004, 60 (28) :5833-5871
[3]  
GREENE TW, 1999, PROTECTIVE GROUPS OR, P127, DOI DOI 10.1002/0471220574.CH2
[4]  
GREENE TW, 1999, PROTECTIVE GROUPS OR, P346
[5]   A highly efficient and chemoselective synthetic protocol for tetrahydropyranylation/depyranylation of alcohols and phenols [J].
Khan, AT ;
Mondal, E ;
Borah, BM ;
Ghosh, S .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2003, 2003 (21) :4113-4117
[6]   Nickel(II) chloride as an efficient and useful catalyst for chemoselective thioacetalization of aldehydes [J].
Khan, AT ;
Mondal, E ;
Sahu, PR ;
Islam, S .
TETRAHEDRON LETTERS, 2003, 44 (05) :919-922
[7]   A highly efficient and useful synthetic protocol for the cleavage of tert-butyldimethylsilyl (TBS) ethers using a catalytic amount of acetyl chloride in dry methanol [J].
Khan, AT ;
Mondal, E .
SYNLETT, 2003, (05) :694-698
[8]  
KOCIENSKI PJ, 1994, PROTECTING GROUPS, P83
[9]   A fast and practical approach to tetrahydropyranylation and depyranylation of alcohols using indium triflate [J].
Mineno, T .
TETRAHEDRON LETTERS, 2002, 43 (44) :7975-7978
[10]   Tetrabutylammonium tribromide (TBATB)-promoted tetrahydropyranylation/depyranylation of alcohols [J].
Naik, S ;
Gopinath, R ;
Patel, BK .
TETRAHEDRON LETTERS, 2001, 42 (43) :7679-7681