Stereoselective Chemical 1,2-cis O-Glycosylation: From ‘Sugar Ray’ to Modern Techniques of the 21st Century

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Abstract
The aim of this account is to discuss the accomplishments made in the area of the stereoselective O-glycosidic bond formation. Particularly, the account is focused on glycosylation methods for the synthesis of 1,2-cis glycosides. 1 Introduction 2 Historical Development 3 Anomeric Effect 4 Mechanistic Considerations 5 Factors Influencing the Stereoselectivity of Glycosylation 6 Anomeric Halides as Glycosyl Donors 6.1 Chlorides, Bromides, and Iodides 6.2 Fluorides 7 1-O Derivatives as Glycosyl Donors 7.1 Hemiacetals 7.2 O-Acyl, O-Carbonyl and Related Compounds 7.3 O-Imidates 7.4 Phosphites, Phosphates and Other O-P Derivatives 7.5 O-Sulfonyl Derivatives 7.6 Anomeric Transglycosylation 8 1-S Derivatives as Glycosyl Donors 8.1 Thioalkyl and Thioaryl Glycosides 8.2 2-Thiopyridyl and Related Cyclic 2-Thioimidates 8.3 Sulfoxides, Sulfimides, and Sulfones 8.4 Xanthates and Related Derivatives 8.5 Thiocyanates and Other Thio Derivatives 9 Miscellaneous and Indirect Methods 9.1 Miscellaneous Glycosyl Donors 9.2 Indirect Approaches 10 Conclusion

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