A novel glycosylation of inactive glycosyl donors using an ionic liquid containing a protic acid under reduced pressure conditions

Yasutaka Kuroiwa; Maiko Sekine; Satoshi Tomono; Daisuke Takahashi; Kazunobu Toshima

doi:10.1016/j.tetlet.2010.09.108

A novel glycosylation of inactive glycosyl donors using an ionic liquid containing a protic acid under reduced pressure conditions

Yasutaka Kuroiwa, Maiko Sekine, Satoshi Tomono, Daisuke Takahashi, Kazunobu Toshima

Department of Applied Chemistry

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

12 Citations (Scopus)

Abstract

The glycosylation of inactive glycosyl donors, such as methyl glycosides and 1-hydroxy sugars with nearly stoichiometric amounts of various alcohols (1.1 equiv) in an ionic liquid containing a protic acid (acid-IL) under reduced pressure conditions proceeded effectively to give the corresponding glycosides in good to high yields. Furthermore, the acid-IL could be reused for additional glycosylations without the loss of efficiency.

Original language	English
Pages (from-to)	6294-6297
Number of pages	4
Journal	Tetrahedron Letters
Volume	51
Issue number	48
DOIs	https://doi.org/10.1016/j.tetlet.2010.09.108
Publication status	Published - 2010 Dec 1

Keywords

Glycosylation
Green chemistry
Inactive sugar
Ionic liquids
Reduced pressure

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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title = "A novel glycosylation of inactive glycosyl donors using an ionic liquid containing a protic acid under reduced pressure conditions",

abstract = "The glycosylation of inactive glycosyl donors, such as methyl glycosides and 1-hydroxy sugars with nearly stoichiometric amounts of various alcohols (1.1 equiv) in an ionic liquid containing a protic acid (acid-IL) under reduced pressure conditions proceeded effectively to give the corresponding glycosides in good to high yields. Furthermore, the acid-IL could be reused for additional glycosylations without the loss of efficiency.",

keywords = "Glycosylation, Green chemistry, Inactive sugar, Ionic liquids, Reduced pressure",

author = "Yasutaka Kuroiwa and Maiko Sekine and Satoshi Tomono and Daisuke Takahashi and Kazunobu Toshima",

note = "Funding Information: This research was supported by the High-Tech Research Center Project for Private Universities: Matching Fund Subsidy, 2006–2011, from the Ministry of Education, Culture, Sports, Science and Technology of Japan (MEXT) . ",

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doi = "10.1016/j.tetlet.2010.09.108",

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T1 - A novel glycosylation of inactive glycosyl donors using an ionic liquid containing a protic acid under reduced pressure conditions

AU - Kuroiwa, Yasutaka

AU - Sekine, Maiko

AU - Tomono, Satoshi

AU - Takahashi, Daisuke

AU - Toshima, Kazunobu

N1 - Funding Information: This research was supported by the High-Tech Research Center Project for Private Universities: Matching Fund Subsidy, 2006–2011, from the Ministry of Education, Culture, Sports, Science and Technology of Japan (MEXT) .

PY - 2010/12/1

Y1 - 2010/12/1

N2 - The glycosylation of inactive glycosyl donors, such as methyl glycosides and 1-hydroxy sugars with nearly stoichiometric amounts of various alcohols (1.1 equiv) in an ionic liquid containing a protic acid (acid-IL) under reduced pressure conditions proceeded effectively to give the corresponding glycosides in good to high yields. Furthermore, the acid-IL could be reused for additional glycosylations without the loss of efficiency.

AB - The glycosylation of inactive glycosyl donors, such as methyl glycosides and 1-hydroxy sugars with nearly stoichiometric amounts of various alcohols (1.1 equiv) in an ionic liquid containing a protic acid (acid-IL) under reduced pressure conditions proceeded effectively to give the corresponding glycosides in good to high yields. Furthermore, the acid-IL could be reused for additional glycosylations without the loss of efficiency.

KW - Glycosylation

KW - Green chemistry

KW - Inactive sugar

KW - Ionic liquids

KW - Reduced pressure

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ER -

A novel glycosylation of inactive glycosyl donors using an ionic liquid containing a protic acid under reduced pressure conditions

Abstract

Keywords

ASJC Scopus subject areas

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