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

Synlett, Table of Contents

CC BY ND NC 4.0 · Synlett 2019; 30(04): 397-400
DOI: 10.1055/s-0037-1611643

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

Seiji Masui

^aDepartment of Chemistry, Graduate School of Science, Osaka University, 1-1 Machikaneyama-cho, Toyonaka, Osaka 560-0043, Japan Email: koichi@chem.sci.osaka-u.ac.jp

,

Yoshiyuki Manabe

^aDepartment of Chemistry, Graduate School of Science, Osaka University, 1-1 Machikaneyama-cho, Toyonaka, Osaka 560-0043, Japan Email: koichi@chem.sci.osaka-u.ac.jp

^bCore for Medicine and Science Collaborative Research and Education, Project Research Center for Fundamental Sciences, Osaka University, 1-1 Machikaneyama-cho, Toyonaka, Osaka 560-0043, Japan

,

Kohtaro Hirao

,

Atsushi Shimoyama

^aDepartment of Chemistry, Graduate School of Science, Osaka University, 1-1 Machikaneyama-cho, Toyonaka, Osaka 560-0043, Japan Email: koichi@chem.sci.osaka-u.ac.jp

^bCore for Medicine and Science Collaborative Research and Education, Project Research Center for Fundamental Sciences, Osaka University, 1-1 Machikaneyama-cho, Toyonaka, Osaka 560-0043, Japan

,

Takahide Fukuyama

^cDepartment of Chemistry, Graduate School of Science, Osaka Prefecture University, Sakai, Osaka 599-8531, Japan

,

Ilhyong Ryu

^cDepartment of Chemistry, Graduate School of Science, Osaka Prefecture University, Sakai, Osaka 599-8531, Japan

,

Koichi Fukase *

^aDepartment of Chemistry, Graduate School of Science, Osaka University, 1-1 Machikaneyama-cho, Toyonaka, Osaka 560-0043, Japan Email: koichi@chem.sci.osaka-u.ac.jp

^bCore for Medicine and Science Collaborative Research and Education, Project Research Center for Fundamental Sciences, Osaka University, 1-1 Machikaneyama-cho, Toyonaka, Osaka 560-0043, Japan

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Abstract

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Published as part of the 30 Years SYNLETT – Pearl Anniversary Issue

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.

Key words

Fischer glycosidation - flow chemistry - furanosides - supported catalysis - carbohydrate - kinetically controlled reaction

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References

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26 General Procedure A flow reactor system consisting of syringe pump, column (φ 4.0 mm × 50 mm, filled with HO-SAS (350 mg, 0.9–1.0 mmol/g loading of SO₃H), backpressure regulator and tubes (inner diameter φ = 50 μm, length L1 = 40 cm, L2 = 10 cm, L3 = 20 cm) was used. A solution of glucose (1, 90 mg, 0.5 mmol) in methanol (5 mL, 0.10 M glucose solution) was filled in the syringe. The syringe was pumped using the syringe pump at flow rates of 0.1 mL/min (residence time = 5 min), and the reaction solution was passed through the column filled with HO-SAS. After the reaction solution came out, the solution was send to the waste for 3 min (priming time = 3 min). Then, the solution was collected for 10 min. After concentration in vacuo, the crude mixture was analyzed by NMR spectroscopy. New HO-SAS was packed each experiments except for the experiments in Scheme 2.

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