Total synthesis and proof of structure of a human breast tumor (Globo-H) antigen

…, JT Randolph, O Kwon, SJ Danishefsky

Index: Park, Tae Kyo; Kim, In Jong; Hu, Shuanghua; Bilodeau, Mark T.; Randolph, John T.; Kwon, Ohyun; Danishefsky, Samuel J. Journal of the American Chemical Society, 1996 , vol. 118, # 46 p. 11488 - 11500

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Citation Number: 96

Abstract

The total synthesis of the Hakomori MBr1 antigen, heavily expressed on human breast tumors, is related. The construction involved the assembly of four glycals:(17 (twice), 18, 20, and 26) and an l-fucose derivative, 34. The sensitivity of the stereochemistry of sulfonamido galactosylation by a terminal galactose ring as a function of the state of protection status of its C4 alcohol was exploited in a key step.(See the formation of compound 51.) The ...