Synthesis and Resolution of a Chiral Open-Chain Host Having a Partial Structure of p-tert-Butylsulfinylcalix[4]arene

Atsuya Sakamoto; Gekko Patria Budiutama; Yoshihiro Takayama; Naoya Morohashi; Tetsutaro Hattori

doi:10.1246/bcsj.20210438

Synthesis and Resolution of a Chiral Open-Chain Host Having a Partial Structure of p-tert-Butylsulfinylcalix[4]arene

Atsuya Sakamoto, Gekko Patria Budiutama, Yoshihiro Takayama, Naoya Morohashi, Tetsutaro Hattori

ENG - Biomolecular Engineering

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

1 Citation (Scopus)

Abstract

An open-chain carboxylic acid host with a chiral sulfinyl group (4) was synthesized from 3,3¤-thiobis[(5-tert-butyl-2-hydroxyphenyl)acetic acid] (2) by oxidation of the epithio linkage with mCPBA, followed by acid-catalyzed monoesterification with propan-1-ol. The monoester was resolved via diastereomeric salt formation using quinidine as a resolving agent. The absolute configuration of (+)-4 was assigned to be (R) by X-ray analysis.

Original language	English
Pages (from-to)	440-442
Number of pages	3
Journal	Bulletin of the Chemical Society of Japan
Volume	95
Issue number	3
DOIs	https://doi.org/10.1246/bcsj.20210438
Publication status	Published - 2022

Keywords

Chiral host
Nanoporous molecular crystal
Optical resolution

ASJC Scopus subject areas

Chemistry(all)

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10.1246/bcsj.20210438

Cite this

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title = "Synthesis and Resolution of a Chiral Open-Chain Host Having a Partial Structure of p-tert-Butylsulfinylcalix[4]arene",

abstract = "An open-chain carboxylic acid host with a chiral sulfinyl group (4) was synthesized from 3,3¤-thiobis[(5-tert-butyl-2-hydroxyphenyl)acetic acid] (2) by oxidation of the epithio linkage with mCPBA, followed by acid-catalyzed monoesterification with propan-1-ol. The monoester was resolved via diastereomeric salt formation using quinidine as a resolving agent. The absolute configuration of (+)-4 was assigned to be (R) by X-ray analysis.",

keywords = "Chiral host, Nanoporous molecular crystal, Optical resolution",

author = "Atsuya Sakamoto and Budiutama, {Gekko Patria} and Yoshihiro Takayama and Naoya Morohashi and Tetsutaro Hattori",

note = "Funding Information: The authors wish to thank Prof. K. Asai for courteous permission to use instruments. The present work was supported by JSPS KAKENHI Grant Numbers 19K05415. Publisher Copyright: {\textcopyright} 2022 Chemical Society of Japan. All rights reserved.",

year = "2022",

doi = "10.1246/bcsj.20210438",

language = "English",

volume = "95",

pages = "440--442",

journal = "Bulletin of the Chemical Society of Japan",

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T1 - Synthesis and Resolution of a Chiral Open-Chain Host Having a Partial Structure of p-tert-Butylsulfinylcalix[4]arene

AU - Sakamoto, Atsuya

AU - Budiutama, Gekko Patria

AU - Takayama, Yoshihiro

AU - Morohashi, Naoya

AU - Hattori, Tetsutaro

N1 - Funding Information: The authors wish to thank Prof. K. Asai for courteous permission to use instruments. The present work was supported by JSPS KAKENHI Grant Numbers 19K05415. Publisher Copyright: © 2022 Chemical Society of Japan. All rights reserved.

PY - 2022

Y1 - 2022

N2 - An open-chain carboxylic acid host with a chiral sulfinyl group (4) was synthesized from 3,3¤-thiobis[(5-tert-butyl-2-hydroxyphenyl)acetic acid] (2) by oxidation of the epithio linkage with mCPBA, followed by acid-catalyzed monoesterification with propan-1-ol. The monoester was resolved via diastereomeric salt formation using quinidine as a resolving agent. The absolute configuration of (+)-4 was assigned to be (R) by X-ray analysis.

AB - An open-chain carboxylic acid host with a chiral sulfinyl group (4) was synthesized from 3,3¤-thiobis[(5-tert-butyl-2-hydroxyphenyl)acetic acid] (2) by oxidation of the epithio linkage with mCPBA, followed by acid-catalyzed monoesterification with propan-1-ol. The monoester was resolved via diastereomeric salt formation using quinidine as a resolving agent. The absolute configuration of (+)-4 was assigned to be (R) by X-ray analysis.

KW - Chiral host

KW - Nanoporous molecular crystal

KW - Optical resolution

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SP - 440

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JO - Bulletin of the Chemical Society of Japan

JF - Bulletin of the Chemical Society of Japan

IS - 3

ER -

Synthesis and Resolution of a Chiral Open-Chain Host Having a Partial Structure of p-tert-Butylsulfinylcalix[4]arene

Abstract

Keywords

ASJC Scopus subject areas

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