A facile chemoselective deprotection of the p-methoxybenzyl group

被引：27
|
作者：
Yu, WS [1 ]
Su, M [1 ]
Gao, XB [1 ]
Yang, ZQ [1 ]
Jin, ZD [1 ]
机构：
[1] Univ Iowa, Coll Pharm, Div Med & Nat Prod Chem, Iowa City, IA 52242 USA
来源：
TETRAHEDRON LETTERS | 2000年 / 41卷 / 21期
关键词：
p-methoxybenzyl group; thioglycosides; orthoganol deprotection;
D O I：
10.1016/S0040-4039(00)00574-8
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The p-methoxybenzyl (PMB) group can be chemoselectively cleaved at low temperature in the presence of SnCl4 and thiophenol. This method is especially useful in the cases where oxidative reagents such as DDQ and CAN need to be avoided. (C) 2000 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码：4015 / 4017
页数：3
相关论文
共 50 条
  • [41] Zeolite-mediated conversion of alcohols to p-methoxybenzyl ethers
    Sharma, GVM
    Punna, S
    Ratnamala, A
    Klumari, VD
    Subrahmanyam, M
    ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL, 2004, 36 (06) : 581 - 586
  • [42] Chemoselective Cleavage of p-Methoxybenzyl and 2-Naphthylmethyl Ethers Using a Catalytic Amount of HCl in Hexafluoro-2-propanol
    Volbeda, Anne Geert
    Kistemaker, Hans An.
    Overkleeft, Herman S.
    van der Marel, Gijsbert A.
    Filippov, Dmitri V.
    Codee, Jeroen D. C.
    JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (17): : 8796 - 8806
  • [43] p-methoxybenzyl ether cleavage by polymer-supported sulfonamides
    Hinklin, RJ
    Kiessling, LL
    ORGANIC LETTERS, 2002, 4 (07) : 1131 - 1133
  • [44] Sulfated tungstate as hydroxyl group activator for preparation of benzyl, including p-methoxybenzyl ethers of alcohols and phenols
    Katkar, Kamlesh V.
    Veer, Sachin D.
    Akamanchi, Krishnacharya G.
    SYNTHETIC COMMUNICATIONS, 2016, 46 (23) : 1893 - 1901
  • [45] Solvent effect in the free-radical oxidation and electrophilic ipso and hydrogen displacement of p-methoxybenzyl alcohol and N-(p-methoxybenzyl)acetamide by Br2
    Bravo, A
    Fontana, F
    Dordi, B
    Minisci, F
    JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (12): : 3880 - 3882
  • [46] Catalytic Aerobic Oxidation of p-Methoxybenzyl (PMB) Ethers to Aldehydes or Ketones
    Zhang, Qian
    Qian, Hui
    Ma, Shengming
    CHEMISTRY-A EUROPEAN JOURNAL, 2025,
  • [47] IODINE IN METHANOL - A SIMPLE SELECTIVE METHOD FOR THE CLEAVAGE OF P-METHOXYBENZYL ETHERS
    VAINO, AR
    SZAREK, WA
    SYNLETT, 1995, (11) : 1157 - &
  • [48] p-methoxybenzyl trityl ether (p-MBTE): A new and improved tritylating reagent
    Sharma, GVM
    Mahalingam, AK
    Prasad, TR
    SYNLETT, 2000, (10) : 1479 - 1481
  • [49] Mild preparation of cephalosporin allyl and p-methoxybenzyl esters using diazoalkanes
    Waddell, ST
    Santorelli, GM
    TETRAHEDRON LETTERS, 1996, 37 (12) : 1971 - 1974
  • [50] Mild preparation of cephalosporin allyl and p-methoxybenzyl esters using diazoalkanes
    Tetrahedron Lett, 12 (1971):
12345