Nucleophilic Deprotection of p-Methoxybenzyl Ethers Using Heterogeneous Oxovanadium Catalyst

Ikeda, Rei; Nishio, Tomoya; Kanomata, Kyohei; Akai, Shuji

doi:https://doi.org/10.1248/cpb.c23-00897

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

アクセス数:65件（2025-04-10 08:45 集計）

固定URL: https://hdl.handle.net/11094/94660

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タイトル	Nucleophilic Deprotection of p-Methoxybenzyl Ethers Using Heterogeneous Oxovanadium Catalyst
著者	著者名 Ikeda, Rei
	著者名 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 著者名 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 著者名 Akai, Shuji
キーワード等	flow reaction
	heterogeneous catalysis
	mesoporous silica
	oxovanadium catalyst
	p-methoxybenzyl ether
	p-methoxyphenylmethyl ether
内容	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.
抄録	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.
出版者	Pharmaceutical Society of Japan
収録物名	Chemical and Pharmaceutical Bulletin
巻(号)	72(2)
ページ	213-219
刊行年月	2024-01-01
言語	英語
ハンドルURL	https://hdl.handle.net/11094/94660
PISSN	00092363
eISSN	13475223
関連情報 (isIdenticalTo)	DOI (出版社版) https://doi.org/10.1248/cpb.c23-00897
アクセス権	open access
権利情報	© 2024 The Pharmaceutical Society of Japan.
出版タイプ	Version of Record
カテゴリ	学術雑誌論文 Journal Article

資源タイプ	学術雑誌論文
ローカル資源タイプ	学術雑誌論文
DCMI資源タイプ	text
DCTERMS.bibliographicCitation	Chemical and Pharmaceutical Bulletin. 2024, 72(2), p. 213-219
DC.title	Nucleophilic Deprotection of p-Methoxybenzyl Ethers Using Heterogeneous Oxovanadium Catalyst
DC.creator	Ikeda, Rei
	Nishio, Tomoya
	Kanomata, Kyohei
	Akai, Shuji
DC.publisher	Pharmaceutical Society of Japan
DC.language' scheme='DCTERMS.RFC1766	英語
DC.type' scheme='DCTERMS.DCMIType	text
DCTERMS.issued' scheme='DCTERMS.W3CDTF	2024-01-01
DC.identifier	https://doi.org/10.1248/cpb.c23-00897
DC.subject	flow reaction
	heterogeneous catalysis
	mesoporous silica
	oxovanadium catalyst
	p-methoxybenzyl ether
	p-methoxyphenylmethyl ether
DC.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.
DCTERMS.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.
DC.rights	© 2024 The Pharmaceutical Society of Japan.
DC.format	94660
citation_title	Nucleophilic Deprotection of p-Methoxybenzyl Ethers Using Heterogeneous Oxovanadium Catalyst
citation_author	Ikeda, Rei
	Nishio, Tomoya
	Kanomata, Kyohei
	Akai, Shuji
citation_publisher	Pharmaceutical Society of Japan
citation_language	英語
citation_date	2024-01-01
citation_journal_title	Chemical and Pharmaceutical Bulletin
citation_volume	72
citation_issue	2
citation_firstpage	213
citation_lastpage	219
citation_doi	https://doi.org/10.1248/cpb.c23-00897
citation_public_url	https://hdl.handle.net/11094/94660

Nucleophilic Deprotection of p-Methoxybenzyl Ethers Using Heterogeneous Oxovanadium Catalyst

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