THE AMINO SUGARS: THE CHEMISTRY AND BIOLOGY OF COMPOUNDS CONTAINING AMINO SUGARS

By MATTHEW ROBINSON

CONTENTS APPLICATIONS OF FLUOROUS TAG METHODOLOGY IN CARBOHYDRATE SYNTHESIS 1 INTRODUCTION 2 WHY USE F-TAGS IN CARBOHYDRATE SYNTHESIS? 3 REDUCING SUGAR ANOMERIC FLUOROUS TAGS AND PONYTAILS 4 TERMINAL PROTECTING GROUP FLUOROUS TAGS 5 LATE-STAGE PROTECTING GROUP FLUOROUS TAGS 6 ITERATIVE PROTECTING GROUP FLUOROUS TAGS 7 ACTIVATABLE FLUOROUS THIOGLYCOSIDE GROUPS 8 N-PROTECTING GROUPS 9 PHOSPHATE PROTECTING GROUPS 10 CONCLUSIONS AND FUTURE DEVELOPMENTS NOTE REFERENCES RECENT PROGRESS IN THE GLYCOSYLATION OF LUPANES 2 GLYCOSYLATION WITH GLYCOSYL HALIDES AND ORTHOESTERS 3 GLYCALS AS GLYCOSYL DONORS 4 GLYCOSYL TRICHLOROACETIMIDATES AS GLYCOSYL DONORS 5 SYNTHESIS OF LUPANE BIDESMOSIDES 6 MISCELLANEOUS GLYCOSYLATION METHODS 7 ACYL MIGRATION AND REARRANGEMENTS DURING THE SYNTHESIS OF LUPANE SAPONINS 8 CYTOTOXIC ACTIVITY OF LUPANE SAPONINS 9 CONCLUSIONS ACKNOWLEDGEMENTS SYNTHETIC ROUTES TARGETING AGROCINOPINES, BACTERIAL CARBOHYDRATE PHOSPHODIESTERS, AND THEIR ANALOGUES 2 SYNTHETIC APPROACHES TOWARDS AGROCINOPINES AND ANALOGUES 3 CONCLUSIONS ADDITION AT THE PROOF STAGE GLYCOSYLATION IN THE GREEN CHEMISTRY ERA 1 WHAT IS GREEN CHEMISTRY? 2 BIOLOGICAL IMPORTANCE OF GLYCOSYLATION 3 GENERAL ASPECTS OF GLYCOSYLATION CHEMISTRY 4 CHEMICAL GLYCOSYLATION 5 SYNTHESIS OF GLYCOSIDES IN ENVIRONMENTALLY BENIGN SOLVENTS 6 DEVELOPMENT OF GLYCOSYL DONOR CHEMISTRY 7 ENZYMATIC GLYCOSYLATIONS 8 ELECTROCHEMICAL GLYCOSYLATIONS 9 PHOTOCHEMICAL GLYCOSYLATIONS 10 SUMMARY SONOGASHIRA CROSS-COUPLING ON CARBOHYDRATE TEMPLATES 2 CARBOHYDRATE-CONNECTED MEDIUM-SIZE CYCLES AND MACROCYCLES 3 CLUSTERS/DENDRIMERS CONTAINING CARBOHYDRATE UNITS 4 SYNTHESIS OF NATURAL PRODUCTS COMPRISING A CARBOHYDRATE MOIETY 5 FUNCTIONALIZED GLYCALS 6 C-GLYCOSIDES 7 FINAL CONSIDERATIONS