Stereoselective glycosylation of hetercyclic bases

Details Stereoselective glycosylation of hetercyclic bases Stereoselective glycosylation of hetercyclic bases

1990-03-02

1992-12-29

Richter, Johann

Organic compounds -- part of the class 532-570 series

Organic compounds

Carbohydrates or derivatives

536 23, 536 24, C07H 1700, C07H 1906

Patent

active

051752670

ABSTRACT:
A method of preparation of 2',3'-dideoxy and 2',3'-dideoxy-2',3'-didehydronucleosides that includes the step of condensing a 1-O-activated-2-(aromatic or aliphatic)-selenenyl-5-O-protected ribose with a protected heterocyclic base in the presence of trimethylsilyl triflate or a Lewis acid to form a .beta.-anomeric nucleoside in high yield.

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Chu, C. K., Beach, J. W., Ullas, G. V. & Kosugi, Y. in Tetrahedron Lett. 29,5349 (1988).
Chu, et al. Nucleosides and Nucleotides 8(5&6), 903 (1989).
Okabe, M., et al, J. Org. Chem. 53,4780 (1988).
Farina, V., and Benigni, D. A., Tetrahedron Lett. 29,1239 (1988).
Niedballa, U. and Vorbruggen, H., J. Org. Chem. 39 (25) 1974.
Hanessian and Murray, Tetrahedron 43, 5055, (1987).
Jones, D. N., Mundy, D., and Whitehouse, R. D., J. Chem. Soc. Chem. Comm. 86 (1970).
Nozaki, K., and Oshima, K., Tetrahedron Lett. 29, 6125 (1988).

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