Mild deprotection of PMB ethers using tert-butyl bromide

被引：6
作者：
Rival, Nicolas [1 ]
Grados, Arantxa Albornoz [2 ]
Schiavo, Lucie [2 ]
Colobert, Francoise [2 ]
Hanquet, Gilles [2 ]
机构：
[1] SINTEF Mat & Chem, NO-0314 Oslo, Norway
[2] Univ Strasbourg, ECPM, CNRS, Lab Synth & Catalyse Associe, F-67087 Strasbourg, France
来源：
TETRAHEDRON LETTERS | 2015年 / 56卷 / 49期
关键词：
PMB ether deprotection; Tert-butyl bromide; Selective deprotection; 4-Methoxybenzyl ether; P-METHOXYBENZYL ETHERS; 4-METHOXYBENZYL MPM ETHERS; SELECTIVE DEPROTECTION; PROTECTING GROUPS; CERIUM(III) CHLORIDE; CLEAVAGE; BENZYL; REMOVAL; ACETALS; FACILE;
D O I：
10.1016/j.tetlet.2015.10.067
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A convenient and high yielding method for the cleavage and scavenging of p-methoxybenzyl protecting group of several alcohols using tert-butyl bromide in refluxing acetonitrile is described. Under these mild conditions other protecting groups such as acid sensitive allyl, benzyl, and Me3CPh2Si ethers, or isopropylidene acetals were unchanged. Interestingly, a selective alkoxy-PMB cleavage was observed in the presence of a PMB phenoxy ether. (C) 2015 Elsevier Ltd. All rights reserved.
引用
收藏
页码：6823 / 6826
页数：4
相关论文
共 39 条
[1]   ALCL3-N,N-DIMETHYLANILINE - A NEW BENZYL AND ALLYL ETHER CLEAVAGE REAGENT [J].
AKIYAMA, T ;
HIROFUJI, H ;
OZAKI, S .
TETRAHEDRON LETTERS, 1991, 32 (10) :1321-1324
[2]  
Bartoli G, 2004, EUR J ORG CHEM, V2004, P2176
[3]  
Bouzide A, 1997, SYNLETT, P1153
[4]   Toward a total synthesis of an aglycone of spiramycin; A chiron approach to the C-1/C-4 and the C-13/C-15 fragments [J].
Breuilles, P ;
Oddon, G ;
Uguen, D .
TETRAHEDRON LETTERS, 1997, 38 (37) :6607-6610
[5]   A simple method for the selective deprotection of p-methoxybenzyl ethers by cerium(III) chloride heptahydrate and sodium iodide [J].
Cappa, A ;
Marcantoni, E ;
Torregiani, E ;
Bartoli, G ;
Bellucci, MC ;
Bosco, M ;
Sambri, L .
JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (15) :5696-5699
[6]   A facile removal of P-methoxybenzyl and diphenylmethyl ester with iodotrimethylsilane-triphenylphosphine [J].
Cha, KH ;
Kang, TW ;
Cho, DO ;
Lee, HW ;
Shin, J ;
Jin, KY ;
Kim, KW ;
Kim, JW ;
Hong, CI .
SYNTHETIC COMMUNICATIONS, 1999, 29 (20) :3533-3540
[7]   KINETICS AND MECHANISM OF SULFOXIDE-SILANE REACTION [J].
CHAN, TH ;
MELNYK, A .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1970, 92 (12) :3718-&
[8]   Proton-exchanged montmorillonite-mediated reactions of methoxybenzyl esters and ethers [J].
Chen, Dongyin ;
Xu, Chang ;
Deng, Jie ;
Jiang, Chunhuan ;
Wen, Xiaoan ;
Kong, Lingyi ;
Zhang, Ji ;
Sun, Hongbin .
TETRAHEDRON, 2014, 70 (11) :1975-1983
[9]   A Synthesis of 3,5-Disubstituted Phenols [J].
Davidson, James P. ;
Sarma, Keshab ;
Fishlock, Dan ;
Welch, Michael H. ;
Sukhtankar, Sunil ;
Lee, Gary M. ;
Martin, Michael ;
Cooper, Gary F. .
ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2010, 14 (02) :477-480
[10]   THE SYNTHESIS AND ABSOLUTE-CONFIGURATION OF THE NOVEL ICHTHYOTOXIC DIACYLGLYCEROLS, UMBRACULUMIN-A AND UMBRACULUMIN-C [J].
DEMEDEIROS, EF ;
HERBERT, JM ;
TAYLOR, RJK .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1991, (11) :2725-2730
1234