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Borinic Acid-Catalyzed Sulfation and Boronic Acid-Promoted Esterification of Carbohydrates

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Borinic Acid-Catalyzed Sulfation and Boronic Acid-Promoted Esterification of Carbohydrates Borinic Acid-Catalyzed Sulfation and Boronic Acid-Promoted Esterification of Carbohydrates by Yu Chen Lin A thesis submitted in conformity with the requirements for the degree of Master of Science Department of Chemistry University of Toronto © Copyright by Yu Chen Lin 2017 Borinic Acid-Catalyzed Sulfation and Boronic Acid-Promoted Esterification of Carbohydrates Yu Chen Lin Master of Science Department of Chemistry University of Toronto 2017 Abstract Carbohydrates and their O-sulfates play important roles in biological functions, including cellular recognition and adhesion, neural processes, fibrosis, growth factor regulation, cancer metastasis, and cellular entry of viruses. However, preparation of sulfated carbohydrates remains a synthetic challenge with conventional methods requiring lengthy protection and deprotection steps. Described herein is our work toward the development of a method for the regioselective sulfation of fully unprotected carbohydrates using a borinic acid catalyst. Via an activated 1,2-cis-borinate intermediate, our method was shown to be robust in the sulfation of a range of substrates, including the synthesis of a sulfated galactosylceramide found in mammalian nervous systems. In addition, work on utilizing boronic acids as protective groups for the preparation of sugar fatty acid ester surfactants is also discussed. ii Acknowledgments I would like to thank my supervisor, Professor Mark Taylor, for the opportunity to join his lab, and his continued support in my studies, research, and pursuits. I am also very grateful to all the Taylor lab members whom I’ve had the pleasure of meeting and working together with. You have all made me feel so at home here, and although it has only been a year, the great memories I’ve had here will stay with me long after. Furthermore, I’d like to give a shout out to my friends in and around the Department for every laughter and drink we’ve shared. Lastly, I would like to thank my family for their unconditional love and support throughout the years and during my degree. iii Table of Contents Acknowledgments .................................................................................................................... iii Table of Contents ..................................................................................................................... iv List of Tables ........................................................................................................................... vi List of Figures ......................................................................................................................... vii List of Abbreviations ............................................................................................................... ix Chapter 1 Introduction ........................................................................................................1 1.1 Sulfated carbohydrates ...................................................................................................1 1.2 Direct, regioselective synthesis of sulfated carbohydrates ............................................4 1.3 Synthesis of sulfated carbohydrates via masked sulfates ............................................11 1.4 Organoboron compounds in carbohydrate chemistry ..................................................18 1.5 Scope of Thesis ............................................................................................................20 Chapter 2 Regioselective, catalytic sulfation of unprotected carbohydrates ....................21 2.1 Sulfation of carbohydrates with 2,2,2-trichloroethyl chlorosulfate .............................21 2.2 Sulfation of carbohydrates with alkyl and aryl 1,2-dimethylimidazolium salt ............22 2.3 Sulfation of carbohydrates with sulfur trioxide amine complexes ..............................29 2.4 Summary and future work ...........................................................................................32 2.5 Experimental ................................................................................................................33 2.5.1. General Information .........................................................................................33 2.5.2. General Procedure A ........................................................................................34 2.5.3. Preparation of catalyst and carbohydrate substrates ........................................34 2.5.4. Synthesis and characterization of compounds .................................................36 Chapter 3 Boronic acid-promoted Fischer esterification ..................................................47 3.1 Introduction ..................................................................................................................47 3.2 Chemical synthesis of sugar fatty acid esters ..............................................................49 3.3 Summary ......................................................................................................................51 3.4 Experimental ................................................................................................................51 3.4.1 General Information .........................................................................................51 3.4.2 General Procedure B ........................................................................................52 3.4.3 Synthesis and characterization of compounds .................................................52 Appendices ...............................................................................................................................58 A1. NMR spectra of reported compounds ..........................................................................58 v List of Tables Table 01. Optimization of methyl 6-O-TBS-α-D-mannopyranoside sulfation with 2,2,2-TCE chlorosulfate ..................................................................................................................................22 Table 02. Optimization of methyl α-L-rhamnopyranoside sulfation with TCE-sulfuryl 1,2- dimethylimidazolium triflate .........................................................................................................24 Table 03. Solvent screen of methyl α-L-rhamnopyranoside sulfation with TCE-sulfuryl 1,2- dimethylimidazolium triflate .........................................................................................................25 Table 04. Boronic acid/Lewis base co-catalyst for sulfation of methyl α-L-rhamnopyranoside ....26 Table 05. Optimization of methyl α-L-rhamnopyranoside sulfation with arylsulfuryl 1,2- dimethylimidazolium triflate .........................................................................................................28 Table 06. Optimization of methyl α-D-mannopyranoside sulfation with sulfur trioxide amine complex .........................................................................................................................................30 Table 07. Optimization of n-octyl α-D-galactopyranoside sulfation with sulfur trioxide amine complex .........................................................................................................................................31 Table 08. Substrate scope of carbohydrate sulfation with SO3-Me3N ...........................................32 Table 09. Substrate scope for fatty acid and sugar alcohol esterification .......................................50 vi List of Figures Figure 01. Structure of select naturally occurring sulfated carbohydrates .......................................2 Figure 02. Structure of the major tri-sulfated disaccharide repeat unit in heparin ...........................3 Figure 03. Structure of heparin derivatives .....................................................................................4 Figure 04. Conventional routes to access various patterns of carbohydrate sulfation ......................5 Figure 05. Transient boronate ester protection in the regioselective sulfation of steroids ...............6 Figure 06. Temperature-dependent regioselective sulfation of galactoside ....................................7 Figure 07. Effect of SO3-amine complexes in the sulfation of trimethylsilyl cellulose ...................8 Figure 08. Regioselective sulfation with dibutyltin oxide of 1,2-cis-diol and 1,2-cis-dioxy ...........9 Figure 09. Regioselective sulfation with dibutyltin oxide of 1,3-cis-diol ......................................10 Figure 10. Regioselective sulfation with dibutyltin oxide in the absence of 1,2-cis-diol ...............10 Figure 11. Routes of nucleophilic attack on a carbohydrate sulfate diester ...................................11 Figure 12. Preparation and unmasking of phenyl sulfate diesters ..................................................12 Figure 13. Preparation and unmasking of alkyl sulfate diesters, a) sulfation with iBu/nP chlorosulfate, b) unmasking of iBu sulfate diesters, c) unmasking of nP sulfate diesters ...............13 Figure 14. Preparation and unmasking of trifluoroethyl sulfate diesters .......................................14 Figure 15. Stability of TFE-masked sulfate diester to further functionalizations ..........................15 Figure 16. Deprotection of TFE-masked sulfate diesters ..............................................................16 Figure 17. Preparation and unmasking of trichloroethyl sulfate diesters .......................................17 Figure 18. Regioselective TCE-masked sulfation of unprotected
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