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Hierarchical and Programmable One-Pot Oligosaccharide Synthesis
Published on: September 6, 2019
A One-Pot Method for Removal of Thioacetyl Group via Desulfurization under Ultraviolet Light To Synthesize
Jian-Tao Ge1,2, Lang Zhou1, Tao Luo1
1Key laboratory of Material Chemistry for Energy Conversion and Storage, Ministry of Education, Hubei Key Laboratory of Bioinorganic Chemistry & Materia Medica, School of Chemistry & Chemical Engineering , Huazhong University of Science & Technology , Luoyu Road 1037 , Wuhan , 430074 , P. R. China.
Abstract:
We herein developed an efficient method for removing thioacetyl to synthesize acylated deoxy glycosides in a one-pot reaction, where the thioacetyl was selectively deacetylated by hydrazine hydrate in DMF within 2-5 min at room temperature, followed by desulfurization under UV light for 1-2 h in the presence of TCEP·HCl. The method was then used to synthesize 2-deoxy glycosides with absolute α/β-configuration via stereoselective control of C-2 thioacetate in glycosylation.
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