Mild debenzylation of aryl benzyl ether with BCl3 in the presence of pentamethylbenzene as a non-lewis-basic cation scavenger

Kentaro Okano; Kei Ichiro Okuyama; Tohru Fukuyama; Hidetoshi Tokuyama

doi:10.1055/S-2008-1077980

Mild debenzylation of aryl benzyl ether with BCl₃ in the presence of pentamethylbenzene as a non-lewis-basic cation scavenger

Kentaro Okano, Kei Ichiro Okuyama, Tohru Fukuyama, Hidetoshi Tokuyama

PHA - Molecular Pharmaceutical Science

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

73 Citations (Scopus)

Abstract

Scope and limitations of the debenzylation conditions for aryl benzyl ether, which was developed during our synthetic studies on yatakemycin, were investigated. The chemoselective debenzylation proceeds at low temperature with a combination of BCl₃ and pentamethylbenzene as a cation scavenger in the presence of various functional groups.

Original language	English
Pages (from-to)	1977-1980
Number of pages	4
Journal	Synlett
Issue number	13
DOIs	https://doi.org/10.1055/S-2008-1077980
Publication status	Published - 2008 Aug 1

Keywords

Aryl benzyl ethers
Debenzylation
Phenols
Protecting groups
Total synthesis

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10.1055/S-2008-1077980

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abstract = "Scope and limitations of the debenzylation conditions for aryl benzyl ether, which was developed during our synthetic studies on yatakemycin, were investigated. The chemoselective debenzylation proceeds at low temperature with a combination of BCl3 and pentamethylbenzene as a cation scavenger in the presence of various functional groups.",

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AU - Okano, Kentaro

AU - Okuyama, Kei Ichiro

AU - Fukuyama, Tohru

AU - Tokuyama, Hidetoshi

PY - 2008/8/1

Y1 - 2008/8/1

N2 - Scope and limitations of the debenzylation conditions for aryl benzyl ether, which was developed during our synthetic studies on yatakemycin, were investigated. The chemoselective debenzylation proceeds at low temperature with a combination of BCl3 and pentamethylbenzene as a cation scavenger in the presence of various functional groups.

AB - Scope and limitations of the debenzylation conditions for aryl benzyl ether, which was developed during our synthetic studies on yatakemycin, were investigated. The chemoselective debenzylation proceeds at low temperature with a combination of BCl3 and pentamethylbenzene as a cation scavenger in the presence of various functional groups.

KW - Aryl benzyl ethers

KW - Debenzylation

KW - Phenols

KW - Protecting groups

KW - Total synthesis

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JF - Synlett

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ER -

Mild debenzylation of aryl benzyl ether with BCl₃ in the presence of pentamethylbenzene as a non-lewis-basic cation scavenger

Abstract

Keywords

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