Sulfoxides, glycosides synthesis

Glycosides, synthesis of, 64, 2 Glycosylating agents, 68, 2 Glycosylation on polymer supports, 68, 2 Glycosylation, with sulfoxides and sulfinates, 64, 2... 

Successful examples were demonstrated for transesterilication, perhydrolysis and ammonolysis (using lipases, esterases, and proteases), amide/peptide synthesis (using proteases), epoxide hydrolysis (using epoxide hydrolases), and glycoside synthesis (using glycosidases). Even redox-transformations, such as carbonyl reduction and sulfoxidation were possible [113-119]. 

The use of sulfoxides as leaving groups in glycoside synthesis is less common, but compound 92 has been employed to couple with a secondary alcohol in the synthesis of hikizimycin (See Chapter 20). 

The crown jewel in the application of the sulfoxide method to the assembly of natural products is the synthesis of a pentasaccharide from the antibiotic moeno-mycin A, wherein each glycosidic bond was formed in a stereocontrolled manner by one variant or another by the sulfoxide method (Scheme 4.63) [373],... 

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