Globo H

M. Adinolfi, A. Iadonisi, A. Ravida, and M. Schiattarella, Versatile use of ytterbium(III) triflate and acid washed molecular sieves in the activation of glycosyl trifluoroacetimidate donors. Assemblage of a biologically relevant tetrasaccharide sequence of Globo H, J. Org. Chem., 70 (2005) 5316-5319. 

SOLID-PHASE SYNTHESIS OF THE HEXASACCHARIDE GLOBO-H ANTIGEN PROGRESS AND LIMITATIONS... 

Scheme 2.18 Solid-phase synthesis of the globo-H trisaccharide antigen.

Scheme 10.3 Preparation of the tumor-associated antigen globo-H by a two-direction...

Slovin SF, Ragupathi G, Adluri S, et al. Carbohydrate vaccines in cancer immunogenicity of a fully synthetic globo H hexasaccharide conjugate in man. Proc Natl Acad Sci USA 1999 96 5710-5715. 

SCHEME 3.28 Programmable one-pot synthesis of Globo-H. CIBn, o-chlorobcnz.yl NBz,... 

Some gangliosides of the globo series (Globo-H, sLcx hexasaccharyl ceramide, etc.) are useful cancer cell markers because they are elevated in the membranes of certain types of tumor cells such as melanomas and metastatic brain tumors. A number of GSLs play a role as tumor-associated carbohydrate antigens (TACAs)... 

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

SCHEME 12.9 Danishefsky s second-generation synthesis of Globo-H. DMF, /V,/V-dimcth-ylformamide DTBP, 2,6-di-tert-butylpyridine IDCP, iodonium di-.vym-collidinc perchlorate LHMDS, lithium bis(trimethylsilyl)amide. 

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