Nucleophilic Deprotection of p-Methoxybenzyl Ethers Using Heterogeneous Oxovanadium Catalyst

Ikeda, Rei; Nishio, Tomoya; Kanomata, Kyohei et al.

Chemical and Pharmaceutical Bulletin, 2024, 72(2), 213-219

Number of Access:555（2025-08-17 20:36 Counts）

Identifier to cite or link to this item: https://hdl.handle.net/11094/94660

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Title
Nucleophilic Deprotection of p-Methoxybenzyl Ethers Using Heterogeneous Oxovanadium Catalyst
Creator
CreatorName
Ikeda, Rei
CreatorName
Nishio, Tomoya
NRID
1000030880447 1000030880447
ORCID
0000-0002-2251-4665 0000-0002-2251-4665
researchmap permalink
kyohei_kanomata kyohei_kanomata
Scopus Author ID
39861733600 39861733600
CreatorName
Kanomata, Kyohei
NRID
1000060192457 1000060192457
researchmap permalink
shuji_akai shuji_akai
Scopus Author ID
7006001526 7006001526
ORCID
0000-0001-9149-8745 0000-0001-9149-8745
CreatorName
Akai, Shuji
Subject
flow reaction
heterogeneous catalysis
mesoporous silica
oxovanadium catalyst
p-methoxybenzyl ether
p-methoxyphenylmethyl ether
Description
Ikeda R., Nishio T., Kanomata K., et al. Nucleophilic Deprotection of p-Methoxybenzyl Ethers Using Heterogeneous Oxovanadium Catalyst. Chemical and Pharmaceutical Bulletin 72, 213 (2024); https://doi.org/10.1248/cpb.c23-00897.
Abstract
Nucleophilic deprotection of p-methoxybenzyl (PMB) [p-methoxyphenylmethyl (MPM)] ethers was developed using a heterogeneous oxovanadium catalyst V-MPS4 and a thiol nucleophile. The deprotection method had a wide reaction scope, including PMB ethers of primary, secondary, and tertiary alcohols bearing various functional groups. In addition, the PMB ether of an oxidation-labile natural product was successfully removed by V-MPS4 catalysis, while a common oxidative method of PMB deprotection afforded a complex mixture. The V-MPS4 catalyst was reusable up to six times without a significant loss in the product yield. The advantages of using the heterogeneous catalyst were further demonstrated by conducting the deprotection reaction in a continuous flow process, which resulted in a 2.7-fold higher catalyst turnover number and 60-fold higher turnover frequency compared to those of the corresponding batch reaction.
Publisher
Pharmaceutical Society of Japan
Source Title
Chemical and Pharmaceutical Bulletin
Volume (Issue)
72(2)
Page
213-219
Date of Issued
2024-01-01
Language
English
Handle URL
https://hdl.handle.net/11094/94660
PISSN
00092363
eISSN
13475223
Relation.isIdenticalTo
DOI (Publisher Version)
https://doi.org/10.1248/cpb.c23-00897
Access Rights
open access
CopyRight
© 2024 The Pharmaceutical Society of Japan.
oaire:version
Version of Record
Category
学術雑誌論文 Journal Article