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Article

Total Synthesis and Proof of Structure of a Human Breast Tumor (Globo-H) Antigen

Supporting Info

Tae Kyo Park,^† In Jong Kim,^† Shuanghua Hu,^† Mark T. Bilodeau,^† John T. Randolph,^† Ohyun Kwon,^†^‡ and Samuel J. Danishefsky*^†^‡

Contribution from the Laboratory for Bioorganic Chemistry, Sloan-Kettering Institute for Cancer Research, 1275 York Avenue, New York, New York 10021, and Department of Chemistry, Columbia University, Havemeyer Hall, New York, New York 10027

J. Am. Chem. Soc., 1996, 118 (46), pp 11488–11500

DOI: 10.1021/ja962048b

Publication Date (Web): November 20, 1996

†

Sloan-Kettering Institute for Cancer Research.

‡

Columbia University.

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

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 synthesis served to confirm the Hakomori assignment of structure, and paves the way for immunoconjugation. (See compound 64.)

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