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Investigation on the Synthesis of α-glycosyl Thiols and the Se-acylation with N-acylbenzotriazoles

Author: JiangJunYan
Tutor: ZhuXiangMing；WangXiaoXia
School: Zhejiang Normal University
Course: Organic Chemistry
Keywords: alpha - glycosyl thiols 1,6 - levoglucosan Trimethylsilyl sulfide Passivation protecting group Ring-opening reaction Acyl benzotriazole Samarium diiodide Diselenide Selenium acylating reaction Selenoesters
CLC: O621.25
Type: Master's thesis
Year: 2011
Downloads: 33
Quote: 0
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Abstract


In this thesis, a novel step stereoselective synthesis of alpha - glycosyl thiol , acyl benzotriazole selenium acylation reaction . The paper is divided into three chapters: the first chapter is an introduction, consists of two parts . The first part introduces the importance of Progress in Synthesis of alpha - glycosyl thiols in the development of carbohydrate chemistry . Acyl benzotriazole of the second part of the application in organic synthesis . The development of a highly stereoselective synthesis of alpha - glycosyl thiol method : under the action of trimethylsilyl triflate ( TMSOTf ) , trimethyl silicon substrate using a commercially available sulfur ether ( TMS ) 2S ] 1,6 - levoglucosan open-loop , high yield and stereoselective a- sugar mercaptan . This chapter 1,6 - dehydrated ether protecting groups on the sugar ring containing passivation base reaction . At this time , the reaction rate and yield have been well reduced, but luckily all the the alpha configuration Sugar mercaptan , to avoid neighboring group participation from happening . Therefore , this method can be a simple and efficient step in the Direct Synthesis of alpha - sugar mercaptan , they can be used to synthesis of various alpha - S - connection of oligosaccharides and sugar conjugates . Chapter research acyl benzotriazole as the acylating agent , organic selenium anion selenium acylation reaction . In samarium diiodide role , reduction of fracture Diselenides the Se - Se bond formation the the selenium the Samarium salt ( RSeSmI2 ) , and the saturated acyl benzotriazole response to higher yield corresponding selenoesters . Acyl benzotriazole as alpha , beta - unsaturated acyl benzotriazole , alpha , beta - unsaturated to yield moderate selenoesters , mainly due to the occurrence of side effects of the double addition .

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CLC: > Mathematical sciences and chemical > Chemistry > Organic Chemistry > Organic Chemistry general issues > Properties of organic compounds > Chemical properties of organic reactions
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