Boron-Wittig Reaction in Carbohydrate Chemistry

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Mini symposium: Glycobiology at the LUMC and beyond

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Boron-Wittig Reaction in Carbohydrate Chemistry

Jakub Zýka 1 , Kamil Parkan 1

1 UCT Prague, Prague 6, Czech Republic

Currently, there is a growing interest in studying carbohydrates and their interactions in organisms, because their recognition could answer many questions about intercellular communication[1,2], which takes part in a wide variety of processes[3,4] such as infection, inflammation, metastasis or immune responses. Understanding and simulating molecular mechanisms of these cellular processes could help to diagnose and treat serious diseases.

O-glycosidic bond of natural oligosaccharides is not suitable for further research and therapeutic use because of its hydrolytic lability. There is therefore an effort to develop and optimize the synthesis of glycosides and oligosaccharides with a stable C-glycosidic bond, which offers better hydrolytic stability, through which they can be used in the research of cellular processes.

Our new universal synthesis of carbohydrate precursors for the preparation of stable C-glycosides or C-oligosaccharides is based on the boron-Wittig reaction[5] of bis[(pinacolato)boryl]methane with appropriately protected carbohydrate aldehydes or ketones 1. The potential of these pinacol-boronates 3 was verified by further transformation to one carbon-extended aldehydes or iodides. Another great potential of these compounds is their use for the sp²-sp² Suzuki-Miyaura reaction[6].

General scheme of Boron-Wittig reaction

Lam, S. K.; Ng, T. B. Appl. Microbiol. Biotechnol. 2011, 89, 45–55.

Ghazarian, H.; Idoni, B. Acta Histochem. 2011, 113 (3), 236–247.

Liu, B.; Bian, H.; Bao, J. Cancer Lett. 2010, 287 (1), 1–12.

Kilpatrick, D. C. Biochem. Biophys. Acta 2002, 1572, 187–197.

Matteson, D. S.; Moody, R. J.; Jesthi, P. K., J. Am. Chem. Soc. 1975, 97, 5608-5609.

Miyaura, N.; Yamada, K.; Suzuki, A., Tetrahedron Lett. 1979, 20, 3437-3440.

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