Synthesis of Globo- and Isoglobo-Series GSLs

SCHEME 12.1 Ogawa s synthesis of Gb. Cer. DAST, AW-diethylaminosulfur trifluoride Tf, triflyl. 

SCHEME 12.2 Nicolaou s synthesis of Gb3Cer. DMAP, 4-dimethylaminopyridine NBS, A-bromosuccinimide TBAF, tetrabutylammonium fluoride. 

Xin-Shan Ye and coworkers [62] carried out the one-pot synthesis of Gb3 and iGb3 using thioglycoside donors with A-(phenylthio)-e-caprolactam (20) and Tf20 as 

SCHEME 12.7 Wang s synthesis of iGb3Cer. DBU, l,8-diazabicyclo[5.4.0]undec-7-ene EDC, l-ethyl-3-(3-dimethylaminopropyl)carbodiimide. 

SCHEME 12.8 Danishefsky s first-generation total synthesis of Globo-H ceramide. DMDO, dimethyldioxirane TIPS, triisopropylsilyl. 

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