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- W2949271335 abstract "A versatile total synthesis of sialylgalactosylgloboside (SGG, 1), carrying the stage-specific embryonic antigen 4 (SSEA-4) is reported, illustrating a more general strategy for the synthesis of complex globo-series glycosphingolipids. Starting from readily available building blocks 7, 8, and 10, two different approaches to the synthesis of the key tetrasaccharide 6 have been developed in a highly convergent manner. Further glycosylations with galactosyl trichloroacetimidate (5) and sialyl phosphite (2) donors successively afforded the penta- and hexasaccharides 3 and 11. The latter was finally converted into the target molecule (SGG, 1) with the help of a azidosphingosine glycosylation procedure, favored in this case by the stereocontrolling properties of the 2a-O-pivaloyl protecting group. Valuable intermediates 6 and 3, having the oligosaccharidic skeletons of Gb4 and Gb5 (SSEA-3), respectively, were obtained in the course of the synthesis." @default.
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- W2949271335 date "2010-08-04" @default.
- W2949271335 modified "2023-09-26" @default.
- W2949271335 title "ChemInform Abstract: Total Synthesis of Sialylgalactosylgloboside: Stage-Specific Embryonic Antigen 4." @default.
- W2949271335 cites W2024348183 @default.
- W2949271335 doi "https://doi.org/10.1002/chin.199709180" @default.
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