Photo-induced glycosylation using a diaryldisulfide as an organo-Lewis photoacid catalyst

Naoto Iibuchi; Takahiro Eto; Manabu Aoyagi; Reiji Kurinami; Hayato Sakai; Taku Hasobe; Daisuke Takahashi; Kazunobu Toshima

doi:10.1039/c9ob02674f

Photo-induced glycosylation using a diaryldisulfide as an organo-Lewis photoacid catalyst

Naoto Iibuchi, Takahiro Eto, Manabu Aoyagi, Reiji Kurinami, Hayato Sakai, Taku Hasobe, Daisuke Takahashi, Kazunobu Toshima

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

9 Citations (Scopus)

Abstract

Photo-induced glycosylations of several acceptors with trichloroacetimidate donors using bis(2-naphthyl)disulfide as an organo-Lewis photoacid (LPA) catalyst proceeded effectively to give the corresponding glycosides in good to high yields. In addition, the ground and excited state absorption spectra of bis(2-naphthyl)disulfide with or without NEt₃ suggested the Lewis acidity of bis(2-naphthyl)disulfide upon photo-irradiation.

Original language	English
Pages (from-to)	851-855
Number of pages	5
Journal	Organic and Biomolecular Chemistry
Volume	18
Issue number	5
DOIs	https://doi.org/10.1039/c9ob02674f
Publication status	Published - 2020

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

Access to Document

10.1039/c9ob02674f

Cite this

@article{32a3e0fc1ea74a70b17e41a160c1e526,

title = "Photo-induced glycosylation using a diaryldisulfide as an organo-Lewis photoacid catalyst",

abstract = "Photo-induced glycosylations of several acceptors with trichloroacetimidate donors using bis(2-naphthyl)disulfide as an organo-Lewis photoacid (LPA) catalyst proceeded effectively to give the corresponding glycosides in good to high yields. In addition, the ground and excited state absorption spectra of bis(2-naphthyl)disulfide with or without NEt3 suggested the Lewis acidity of bis(2-naphthyl)disulfide upon photo-irradiation.",

author = "Naoto Iibuchi and Takahiro Eto and Manabu Aoyagi and Reiji Kurinami and Hayato Sakai and Taku Hasobe and Daisuke Takahashi and Kazunobu Toshima",

note = "Funding Information: This research was supported in part by a grant for Scientific Research (B) (No. JP19H02724) from the Ministry of Education, Culture, Sports, Science and Technology of Japan (MEXT). Publisher Copyright: {\textcopyright} 2020 The Royal Society of Chemistry.",

year = "2020",

doi = "10.1039/c9ob02674f",

language = "English",

volume = "18",

pages = "851--855",

journal = "Organic and Biomolecular Chemistry",

issn = "1477-0520",

publisher = "Royal Society of Chemistry",

number = "5",

}

TY - JOUR

T1 - Photo-induced glycosylation using a diaryldisulfide as an organo-Lewis photoacid catalyst

AU - Iibuchi, Naoto

AU - Eto, Takahiro

AU - Aoyagi, Manabu

AU - Kurinami, Reiji

AU - Sakai, Hayato

AU - Hasobe, Taku

AU - Takahashi, Daisuke

AU - Toshima, Kazunobu

N1 - Funding Information: This research was supported in part by a grant for Scientific Research (B) (No. JP19H02724) from the Ministry of Education, Culture, Sports, Science and Technology of Japan (MEXT). Publisher Copyright: © 2020 The Royal Society of Chemistry.

PY - 2020

Y1 - 2020

N2 - Photo-induced glycosylations of several acceptors with trichloroacetimidate donors using bis(2-naphthyl)disulfide as an organo-Lewis photoacid (LPA) catalyst proceeded effectively to give the corresponding glycosides in good to high yields. In addition, the ground and excited state absorption spectra of bis(2-naphthyl)disulfide with or without NEt3 suggested the Lewis acidity of bis(2-naphthyl)disulfide upon photo-irradiation.

AB - Photo-induced glycosylations of several acceptors with trichloroacetimidate donors using bis(2-naphthyl)disulfide as an organo-Lewis photoacid (LPA) catalyst proceeded effectively to give the corresponding glycosides in good to high yields. In addition, the ground and excited state absorption spectra of bis(2-naphthyl)disulfide with or without NEt3 suggested the Lewis acidity of bis(2-naphthyl)disulfide upon photo-irradiation.

UR - http://www.scopus.com/inward/record.url?scp=85079018713&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85079018713&partnerID=8YFLogxK

U2 - 10.1039/c9ob02674f

DO - 10.1039/c9ob02674f

M3 - Article

C2 - 31939472

AN - SCOPUS:85079018713

VL - 18

SP - 851

EP - 855

JO - Organic and Biomolecular Chemistry

JF - Organic and Biomolecular Chemistry

SN - 1477-0520

IS - 5

ER -

Photo-induced glycosylation using a diaryldisulfide as an organo-Lewis photoacid catalyst

Abstract

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this