A facile zirconium(IV) chloride catalysed selective deprotection of t-butyldimethylsilyl (TBDMS) ethers

被引:42
|
作者
Sharma, GVM [1 ]
Srinivas, B [1 ]
Krishna, PR [1 ]
机构
[1] Indian Inst Chem Technol, Div Organ Chem 3, Discovery Lab, Hyderabad 500007, Andhra Pradesh, India
关键词
TBDMS ethers; zirconium(IV) chloride; desilylation; protecting groups;
D O I
10.1016/S0040-4039(03)01088-8
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A simple and efficient protocol for the selective deprotection of t-butyldimethylsilyl (TBDMS) ethers using 20 mol% ZrCl4 in 20-45 min and in high yields, is reported, wherein it is demonstrated that acid and base sensitive groups and allylic and benzylic groups are unaffected. (C) 2003 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:4689 / 4691
页数:3
相关论文
共 50 条
  • [41] Deprotection of tert-butyldimethylsilyl (TBDMS) ethers using efficient and recyclable heterogeneous silver salt of silicotungstic acid catalyst under mild reaction condition
    Jadhav, Arvind H.
    Chinnappan, Amutha
    Patil, Roopa H.
    Chung, Wook-Jin
    Kim, Hern
    CHEMICAL ENGINEERING JOURNAL, 2014, 236 : 300 - 305
  • [42] The selective deprotection of thioesters using titanium(IV) chloride/zinc
    Jin, CK
    Jeong, HJ
    Kim, MK
    Kim, JY
    Yoon, YJ
    Lee, SG
    SYNLETT, 2001, (12) : 1956 - 1958
  • [43] A mild and selective cleavage of tert-butyldimethylsilyl ethers by indium(III) chloride
    Yadav, JS
    Reddy, BVS
    Madan, C
    NEW JOURNAL OF CHEMISTRY, 2000, 24 (11) : 853 - 854
  • [44] Facile aromatic Claisen rearrangement catalysed by Tin(IV) chloride
    Sarkar, Debayan
    Venkateswaran, Ramanathapuram V.
    SYNLETT, 2008, (05) : 653 - 654
  • [45] Zirconium(IV) chloride catalyzed new and efficient protocol for the selective cleavage of p-methoxybenzyl ethers
    Sharma, GVM
    Reddy, CG
    Krishna, PR
    JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (11): : 4574 - 4575
  • [46] Zirconium(IV) chloride-silica catalysed thioacetalisation of carbonyl compounds
    Patney, HK
    Margan, S
    TETRAHEDRON LETTERS, 1996, 37 (26) : 4621 - 4622
  • [47] Iodine and its interhalogen compounds:: Versatile reagents in carbohydrate chemistry IX.: A mild and selective deprotection of tert-butyldimethylsilyl (TBDMS) ethers in the presence of various protecting groups using iodine monobromide
    Kartha, KPR
    Field, RA
    SYNLETT, 1999, (03) : 311 - 312
  • [48] A mild, efficient and selective deprotection of t-butyldimethylsilyl-protected phenols using cesium carbonate
    Jiang, ZY
    Wang, YG
    TETRAHEDRON LETTERS, 2003, 44 (19) : 3859 - 3861
  • [49] Selective deprotection of tert-butyldimethylsilyl ethers using Nafion-H®/sodium iodide (or bromodimethylsulfonium bromide) in methanol
    Rani, S
    Babu, JL
    Vankar, YD
    SYNTHETIC COMMUNICATIONS, 2003, 33 (23) : 4043 - 4052
  • [50] HF-Pyridine: A Versatile Promoter for Monoacylation/Sulfonylation of Phenolic Plots and for Direct Conversion of t-Butyldimethylsilyl Ethers to the Corresponding Acetates
    Michigami, Kyosuke
    Yoshimoto, Kazuya
    Hayashi, Masahiko
    CHEMISTRY LETTERS, 2012, 41 (02) : 138 - 139