4-Nitrobenzyl group for protection of hydroxyl functions

Koichi Kukase; Hideo Tanaka; Sigeru Toriib; Shoichi Kusumoto

doi:10.1016/S0040-4039(00)94562-3

4-Nitrobenzyl group for protection of hydroxyl functions

Koichi Kukase, Hideo Tanaka, Sigeru Toriib, Shoichi Kusumoto

Faculty of Engineering

Research output: Contribution to journal › Article › peer-review

36 Citations (Scopus)

Abstract

Versatile use of 4-nitrobenzyl group for protection of hydroxyl functions is described. It can be removed selectively in the presence of other benzyl-type protecting groups such as benzyl and 4-methoxybenzyl via reduction into 4-aminobenzyl group followed by electrochemical oxidation. Very clean oxidative cleavage of 4-aminobenzyl group could also be effected with 2,3-dichloro-5,6-dicyanobenzoquinone after N-acetylation.

Original language	English
Pages (from-to)	389-392
Number of pages	4
Journal	Tetrahedron Letters
Volume	31
Issue number	3
DOIs	https://doi.org/10.1016/S0040-4039(00)94562-3
Publication status	Published - 1990

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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title = "4-Nitrobenzyl group for protection of hydroxyl functions",

abstract = "Versatile use of 4-nitrobenzyl group for protection of hydroxyl functions is described. It can be removed selectively in the presence of other benzyl-type protecting groups such as benzyl and 4-methoxybenzyl via reduction into 4-aminobenzyl group followed by electrochemical oxidation. Very clean oxidative cleavage of 4-aminobenzyl group could also be effected with 2,3-dichloro-5,6-dicyanobenzoquinone after N-acetylation.",

author = "Koichi Kukase and Hideo Tanaka and Sigeru Toriib and Shoichi Kusumoto",

note = "Funding Information: This work was dedicated on the occasion of Prof. Haruaki Yajima{\textquoteright}s retirement from Kyoto University. A part of this work was supported by Grand-in-Aid for Scientific Research (No. 01470028) from the Ministry of Education, Science and Culture.",

year = "1990",

doi = "10.1016/S0040-4039(00)94562-3",

language = "English",

volume = "31",

pages = "389--392",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier Limited",

number = "3",

}

TY - JOUR

T1 - 4-Nitrobenzyl group for protection of hydroxyl functions

AU - Kukase, Koichi

AU - Tanaka, Hideo

AU - Toriib, Sigeru

AU - Kusumoto, Shoichi

N1 - Funding Information: This work was dedicated on the occasion of Prof. Haruaki Yajima’s retirement from Kyoto University. A part of this work was supported by Grand-in-Aid for Scientific Research (No. 01470028) from the Ministry of Education, Science and Culture.

PY - 1990

Y1 - 1990

N2 - Versatile use of 4-nitrobenzyl group for protection of hydroxyl functions is described. It can be removed selectively in the presence of other benzyl-type protecting groups such as benzyl and 4-methoxybenzyl via reduction into 4-aminobenzyl group followed by electrochemical oxidation. Very clean oxidative cleavage of 4-aminobenzyl group could also be effected with 2,3-dichloro-5,6-dicyanobenzoquinone after N-acetylation.

AB - Versatile use of 4-nitrobenzyl group for protection of hydroxyl functions is described. It can be removed selectively in the presence of other benzyl-type protecting groups such as benzyl and 4-methoxybenzyl via reduction into 4-aminobenzyl group followed by electrochemical oxidation. Very clean oxidative cleavage of 4-aminobenzyl group could also be effected with 2,3-dichloro-5,6-dicyanobenzoquinone after N-acetylation.

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UR - http://www.scopus.com/inward/citedby.url?scp=0025157115&partnerID=8YFLogxK

U2 - 10.1016/S0040-4039(00)94562-3

DO - 10.1016/S0040-4039(00)94562-3

M3 - Article

AN - SCOPUS:0025157115

VL - 31

SP - 389

EP - 392

JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

IS - 3

ER -

4-Nitrobenzyl group for protection of hydroxyl functions

Abstract

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