Kinetically Controlled Fischer Glycosidation under Flow Conditions: A New Method for Preparing Furanosides

Seiji Masui; Yoshiyuki Manabe; Kohtaro Hirao; Atsushi Shimoyama; Takahide Fukuyama; Ilhyong Ryu; Koichi Fukase

doi:10.1055/s-0037-1611643

Kinetically Controlled Fischer Glycosidation under Flow Conditions: A New Method for Preparing Furanosides

Seiji Masui, Yoshiyuki Manabe, Kohtaro Hirao, Atsushi Shimoyama, Takahide Fukuyama, Ilhyong Ryu, Koichi Fukase^*

^*Corresponding author for this work

Department of Applied Chemistry

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

18 Scopus citations

Abstract

Kinetically controlled Fischer glycosidation was achieved under flow conditions. β-Hydroxy-substituted sulfonic acid functionalized silica (HO-SAS) was used as an acid catalyst. This reaction directly converted aldohexoses into kinetically favored furanosides to enable the practical synthesis of furanosides. After optimization of the reaction temperature and residence time, glucofuranosides, galactofuranosides, and mannofuranosides were synthesized in good yields.

Original language	English
Pages (from-to)	397-400
Number of pages	4
Journal	Synlett
Volume	30
Issue number	4
DOIs	https://doi.org/10.1055/s-0037-1611643
State	Published - 2019

Keywords

Fischer glycosidation
carbohydrate
flow chemistry
furanosides
kinetically controlled reaction
supported catalysis

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10.1055/s-0037-1611643

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title = "Kinetically Controlled Fischer Glycosidation under Flow Conditions: A New Method for Preparing Furanosides",

abstract = "Kinetically controlled Fischer glycosidation was achieved under flow conditions. β-Hydroxy-substituted sulfonic acid functionalized silica (HO-SAS) was used as an acid catalyst. This reaction directly converted aldohexoses into kinetically favored furanosides to enable the practical synthesis of furanosides. After optimization of the reaction temperature and residence time, glucofuranosides, galactofuranosides, and mannofuranosides were synthesized in good yields.",

keywords = "Fischer glycosidation, carbohydrate, flow chemistry, furanosides, kinetically controlled reaction, supported catalysis",

author = "Seiji Masui and Yoshiyuki Manabe and Kohtaro Hirao and Atsushi Shimoyama and Takahide Fukuyama and Ilhyong Ryu and Koichi Fukase",

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T1 - Kinetically Controlled Fischer Glycosidation under Flow Conditions

T2 - A New Method for Preparing Furanosides

AU - Masui, Seiji

AU - Manabe, Yoshiyuki

AU - Hirao, Kohtaro

AU - Shimoyama, Atsushi

AU - Fukuyama, Takahide

AU - Ryu, Ilhyong

AU - Fukase, Koichi

N1 - Publisher Copyright: © Georg Thieme Verlag.

PY - 2019

Y1 - 2019

N2 - Kinetically controlled Fischer glycosidation was achieved under flow conditions. β-Hydroxy-substituted sulfonic acid functionalized silica (HO-SAS) was used as an acid catalyst. This reaction directly converted aldohexoses into kinetically favored furanosides to enable the practical synthesis of furanosides. After optimization of the reaction temperature and residence time, glucofuranosides, galactofuranosides, and mannofuranosides were synthesized in good yields.

AB - Kinetically controlled Fischer glycosidation was achieved under flow conditions. β-Hydroxy-substituted sulfonic acid functionalized silica (HO-SAS) was used as an acid catalyst. This reaction directly converted aldohexoses into kinetically favored furanosides to enable the practical synthesis of furanosides. After optimization of the reaction temperature and residence time, glucofuranosides, galactofuranosides, and mannofuranosides were synthesized in good yields.

KW - Fischer glycosidation

KW - carbohydrate

KW - flow chemistry

KW - furanosides

KW - kinetically controlled reaction

KW - supported catalysis

UR - http://www.scopus.com/inward/record.url?scp=85061899197&partnerID=8YFLogxK

U2 - 10.1055/s-0037-1611643

DO - 10.1055/s-0037-1611643

M3 - Article

AN - SCOPUS:85061899197

SN - 0936-5214

VL - 30

SP - 397

EP - 400

JO - Synlett

JF - Synlett

IS - 4

ER -

Kinetically Controlled Fischer Glycosidation under Flow Conditions: A New Method for Preparing Furanosides

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Keywords

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