Direct Synthesis of Unsaturated Sugars from Methyl Glycosides

Ji Cao; Masazumi Tamura; Yoshinao Nakagawa; Keiichi Tomishige

doi:10.1021/acscatal.9b00589

Direct Synthesis of Unsaturated Sugars from Methyl Glycosides

Ji Cao, Masazumi Tamura, Yoshinao Nakagawa, Keiichi Tomishige

ENG - Applied Chemistry

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

23 Citations (Scopus)

Abstract

Transformation of sugars without protection of the OH groups is an ideal method and a powerful tool for biomass utilization, and particularly, unsaturated sugars are a promising target because they can be transformed to versatile chemicals because of the olefin group. Herein, we demonstrated direct transformation of various methyl glycosides, which can be easily obtained from sugar derivatives, without protection of the OH groups to the corresponding unsaturated sugars with maintaining their original stereostructures in high selectivities and yields (up to 90%) using ReO_x-Au/CeO₂ catalyst at low H₂ pressure (≤1.2 MPa) by deoxydehydration.

Original language	English
Pages (from-to)	3725-3729
Number of pages	5
Journal	ACS Catalysis
Volume	9
Issue number	4
DOIs	https://doi.org/10.1021/acscatal.9b00589
Publication status	Published - 2019 Apr 5

Keywords

deoxydehydration
heterogeneous catalyst
rhenium
sugar conversion
unsaturated sugars

ASJC Scopus subject areas

Catalysis
Chemistry(all)

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10.1021/acscatal.9b00589

Cite this

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title = "Direct Synthesis of Unsaturated Sugars from Methyl Glycosides",

abstract = "Transformation of sugars without protection of the OH groups is an ideal method and a powerful tool for biomass utilization, and particularly, unsaturated sugars are a promising target because they can be transformed to versatile chemicals because of the olefin group. Herein, we demonstrated direct transformation of various methyl glycosides, which can be easily obtained from sugar derivatives, without protection of the OH groups to the corresponding unsaturated sugars with maintaining their original stereostructures in high selectivities and yields (up to 90%) using ReOx-Au/CeO2 catalyst at low H2 pressure (≤1.2 MPa) by deoxydehydration.",

keywords = "deoxydehydration, heterogeneous catalyst, rhenium, sugar conversion, unsaturated sugars",

author = "Ji Cao and Masazumi Tamura and Yoshinao Nakagawa and Keiichi Tomishige",

note = "Funding Information: This work was supported by Grant-in-Aid for Challenging Exploratory (18K18965) and partially supported by Grant-in-Aid for Scientific Research (S) (18H05247) from JSPS. Ji Cao thanks the China Scholarship Council for the financial support. Publisher Copyright: Copyright {\textcopyright} 2019 American Chemical Society.",

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T1 - Direct Synthesis of Unsaturated Sugars from Methyl Glycosides

AU - Cao, Ji

AU - Tamura, Masazumi

AU - Nakagawa, Yoshinao

AU - Tomishige, Keiichi

N1 - Funding Information: This work was supported by Grant-in-Aid for Challenging Exploratory (18K18965) and partially supported by Grant-in-Aid for Scientific Research (S) (18H05247) from JSPS. Ji Cao thanks the China Scholarship Council for the financial support. Publisher Copyright: Copyright © 2019 American Chemical Society.

PY - 2019/4/5

Y1 - 2019/4/5

N2 - Transformation of sugars without protection of the OH groups is an ideal method and a powerful tool for biomass utilization, and particularly, unsaturated sugars are a promising target because they can be transformed to versatile chemicals because of the olefin group. Herein, we demonstrated direct transformation of various methyl glycosides, which can be easily obtained from sugar derivatives, without protection of the OH groups to the corresponding unsaturated sugars with maintaining their original stereostructures in high selectivities and yields (up to 90%) using ReOx-Au/CeO2 catalyst at low H2 pressure (≤1.2 MPa) by deoxydehydration.

AB - Transformation of sugars without protection of the OH groups is an ideal method and a powerful tool for biomass utilization, and particularly, unsaturated sugars are a promising target because they can be transformed to versatile chemicals because of the olefin group. Herein, we demonstrated direct transformation of various methyl glycosides, which can be easily obtained from sugar derivatives, without protection of the OH groups to the corresponding unsaturated sugars with maintaining their original stereostructures in high selectivities and yields (up to 90%) using ReOx-Au/CeO2 catalyst at low H2 pressure (≤1.2 MPa) by deoxydehydration.

KW - deoxydehydration

KW - heterogeneous catalyst

KW - rhenium

KW - sugar conversion

KW - unsaturated sugars

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Direct Synthesis of Unsaturated Sugars from Methyl Glycosides

Abstract

Keywords

ASJC Scopus subject areas

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