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
a  Department 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
a  Department 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
b  Core 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
a  Department 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
b  Core 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
c  Department of Chemistry, Graduate School of Science, Osaka Prefecture University, Sakai, Osaka 599-8531, Japan
,
Ilhyong Ryu
c  Department of Chemistry, Graduate School of Science, Osaka Prefecture University, Sakai, Osaka 599-8531, Japan
,
a  Department 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
b  Core 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
› Author Affiliations

This work was financially supported in part by JSPS KAKENHI Grant Number 15H05836 in Middle Molecular Strategy, JSPS KAKENHI Grant Number 16H01885, JSPS KAKENHI Grant Number 16H05924, and JSPS KAKENHI Grant Number 18H04620.
Further Information

Publication History

Received: 28 September 2018

Accepted after revision: 03 December 2018

Publication Date:
07 January 2019 (eFirst)

  

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.

Supporting Information

 
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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.