Lewis Acid Promoted Deprotection of Benzylidene Acetals and p-Methoxybenzyl Ethers with Mercaptoacid Acid as Scavenger

被引：2
|
作者：
Greve, Rasmus D. [1 ]
Jensen, Henrik H. [1 ]
机构：
[1] Aarhus Univ, DK-8000 Aarhus, Denmark
来源：
ORGANIC LETTERS | 2023年 / 25卷 / 20期
关键词：
BY-PRODUCTS; CLEAVAGE; REMOVAL; NAP; PHASE;
D O I：
10.1021/acs.orglett.3c00958
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
We demonstrate a new and high-yieldingmethod for removalof benzylideneacetals and para-methoxybenzyl ethers under catalyticconditions (BF3:OEt2 orFeCl(3), 10mol%) with mercaptoacetic acid as a scavenger. The reaction coproductsare converted to water-soluble molecules, which can be removed byaqueous extraction, thereby bypassing the need for chromatographicpurification. The reaction was demonstrated on both multimilligramand multigram scale.
引用
收藏
页码：3628 / 3632
页数：5
相关论文
共 50 条
  • [1] Lewis acid-catalyzed deprotection of p-methoxybenzyl ether
    Bouzide, A
    Sauve, G
    SYNLETT, 1997, (10) : 1153 - &
  • [2] Regioselective deprotection of p-methoxybenzyl ethers of furanose derivatives
    Bouzide, A
    Sauvé, G
    TETRAHEDRON LETTERS, 1999, 40 (15) : 2883 - 2886
  • [3] Oxidative Deprotection of p-Methoxybenzyl Ethers by a Nitroxyl Radical Catalyst
    Hamada, Shohei
    YAKUGAKU ZASSHI-JOURNAL OF THE PHARMACEUTICAL SOCIETY OF JAPAN, 2021, 141 (10): : 1147 - 1154
  • [4] Nucleophilic Deprotection of p-Methoxybenzyl Ethers Using Heterogeneous Oxovanadium Catalyst
    Ikeda, Rei
    Nishio, Tomoya
    Kanomata, Kyohei
    Akai, Shuji
    CHEMICAL & PHARMACEUTICAL BULLETIN, 2024, 72 (02) : 213 - 219
  • [5] Silver(I)-Catalyzed Deprotection of p-Methoxybenzyl Ethers: A Mild and Chemoselective Method
    Kern, Nicolas
    Dombray, Thomas
    Blanc, Aurelien
    Weibel, Jean-Marc
    Pale, Patrick
    JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (20): : 9227 - 9235
  • [6] Deprotection of benzyl and p-methoxybenzyl ethers by chlorosulfonyl isocyanate-sodium hydroxide
    Kim, JD
    Han, G
    Zee, OP
    Jung, YH
    TETRAHEDRON LETTERS, 2003, 44 (04) : 733 - 735
  • [7] P-METHOXYBENZYL ETHERS AS ACID-LABILE PROTECTING GROUPS IN OLIGOSACCHARIDE SYNTHESIS
    YAN, L
    KAHNE, D
    SYNLETT, 1995, (05) : 523 - 524
  • [8] Oxidative Deprotection of p-Methoxybenzyl Ethers via Metal-Free Photoredox Catalysis
    Ahn, Deok Kyun
    Kang, Young Woo
    Woo, Sang Kook
    JOURNAL OF ORGANIC CHEMISTRY, 2019, 84 (06): : 3612 - 3623
  • [9] Deprotection of benzyl and p-methoxybenzyl ethers by chlorosulfonyl isocyanate-sodium hydroxide.
    Kim, JD
    Han, GH
    Zee, OP
    Jung, YH
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2002, 224 : U227 - U227
  • [10] p-methoxybenzyl group as a protecting group of the nitrogen in indole derivatives: Deprotection by DDQ or trifluoroacetic acid
    Miki, Y
    Hachiken, H
    Kashima, Y
    Sugimura, W
    Yanase, N
    HETEROCYCLES, 1998, 48 (01) : 1 - 4
12345