A simple and highly efficient deprotecting method for methoxymethyl and methoxyethoxymethyl ethers and methoxyethoxymethyl esters

被引:0
|
作者
Lee, ASY [1 ]
Hu, YJ [1 ]
Chu, SF [1 ]
机构
[1] Tamkang Univ, Dept Chem, Tamsui 25137, Taiwan
关键词
MEM-esters; MOM-ethers; deprotection;
D O I
暂无
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A series of methoxyethoxymethyl (MEM)- and methoxymethyl (MOM)-ethers and MEM-esters were hydrolyzed to their corresponding alcohols and carboxylic acids by a catalytic amount of CBr4 (10%) in iPrOH under refluxing reaction condition. The chemoselective hydrolysis between R3Si- and MEM-protected alcohols can be achieved by using different steric bulkness solvents such as MeOH or iPrOH. (C) 2001 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:2121 / 2126
页数:6
相关论文
共 50 条
  • [1] AN EFFICIENT DEPROTECTIVE METHOD FOR ALLYLIC ALCOHOLS PROTECTED AS METHOXYETHOXYMETHYL (MEM) AND METHOXYMETHYL (MOM) ETHERS
    MONTI, H
    LEANDRI, G
    KLOSRINGUET, M
    CORRIOL, C
    SYNTHETIC COMMUNICATIONS, 1983, 13 (12) : 1021 - 1026
  • [2] An efficient and selective deprotecting method for methoxymethyl ethers
    Peng, YG
    Ji, CY
    Chen, YC
    Huang, CZ
    Jiang, YZ
    SYNTHETIC COMMUNICATIONS, 2004, 34 (23) : 4325 - 4330
  • [3] A highly efficient, mild, and selective cleavage of β-methoxyethoxymethyl (MEM) ethers by cerium(III) chloride in acetonitrile
    Sabitha, G
    Babu, RS
    Rajkumar, M
    Srividya, R
    Yadav, JS
    ORGANIC LETTERS, 2001, 3 (08) : 1149 - 1151
  • [4] MILD DEPROTECTION OF METHOXYMETHYL ESTERS, METHYLTHIOMETHYL ESTERS, METHOXYETHOXYMETHYL ESTERS, AND BETA-(TRIMETHYLSILYL)ETHOXYMETHYL ESTERS WITH MAGNESIUM BROMIDE IN ETHER
    KIM, S
    PARK, YH
    KEE, IS
    TETRAHEDRON LETTERS, 1991, 32 (26) : 3099 - 3100
  • [5] SHIKIMATE DERIVED METABOLITES .9. A COMMENT ON THE REACTIVITY OF METHOXYMETHYL (MOM) AND BETA-METHOXYETHOXYMETHYL (MEM) ESTERS
    YOUNG, SD
    COBLENS, KE
    GANEM, B
    TETRAHEDRON LETTERS, 1981, 22 (49) : 4887 - 4888
  • [6] A LEWIS ACID-CATALYZED PROCEDURE FOR THE CONVERSION OF 2-METHOXYETHOXYMETHYL ETHERS TO CARBOXYLIC ESTERS
    GROSS, RS
    WATT, DS
    SYNTHETIC COMMUNICATIONS, 1987, 17 (15) : 1749 - 1760
  • [7] An efficient and highly selective deprotecting method for β-(trimethylsilyl)ethoxymethyl ethers
    Chen, MY
    Lee, ASY
    JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (04): : 1384 - 1387
  • [8] Synthesis of Ionic Liquids Equipped with 2-Methoxyethoxymethyl/Methoxymethyl Groups Using a Simple Microreactor System
    Nokami, Toshiki
    Matsumoto, Kuninobu
    Itoh, Taka-aki
    Fukaya, Yukinobu
    Itoh, Toshiyuki
    ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2014, 18 (11) : 1367 - 1371
  • [9] MILD DEPROTECTION OF METHYL, BENZYL, METHOXYMETHYL, METHYLTHIOMETHYL, METHOXYETHOXYMETHYL, AND BETA-(TRIMETHYLSILYL)ETHOXYMETHYL ESTERS WITH ALCL3-N,N-DIMETHYLANILINE
    AKIYAMA, T
    HIROFUJI, H
    HIROSE, A
    OZAKI, S
    SYNTHETIC COMMUNICATIONS, 1994, 24 (15) : 2179 - 2185
  • [10] Highly efficient and convenient deprotection of methoxymethyl ethers and esters using bismuth triflate in an aqueous medium
    Reddy, SV
    Rao, RJ
    Kumar, US
    Rao, JM
    CHEMISTRY LETTERS, 2003, 32 (11) : 1038 - 1039