Title of article
Synergistic solvent effect in 1,2-cis-glycoside formation
Author/Authors
Akihiro Ishiwata، نويسنده , , Yuichi Munemura، نويسنده , , Yukishige Ito، نويسنده ,
Issue Information
هفته نامه با شماره پیاپی سال 2008
Pages
11
From page
92
To page
102
Abstract
Construction of three continuous 1,2-cis-α-glucosidic linkages was achieved in optimized solvent system. High-throughput optimization was conducted, by using substrates protected by perdeuterated benzyl (Bn-d7) groups. It enabled facile evaluation of yield and stereoselectivity with 1H NMR and MALDI-TOF MS, respectively. We found that CHCl3 and ethereal solvent had a synergetic effect to enhance the α-selectivity. The optimized solvent systems in CHCl3/CPME and CHCl3/Et2O were applied to the linear synthesis of Glcα1→2Glcα1→3Glcα1→3Man (Glc3Man1), which was achieved in 86% overall stereoselectivity.
Keywords
?-Glucoside , Stereoselective , 1 , 2-cis-Glycosylation , Solvent effect
Journal title
Tetrahedron
Serial Year
2008
Journal title
Tetrahedron
Record number
1093599
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