Process for preparing 2-deoxynucleosides

Details Process for preparing 2-deoxynucleosides Process for preparing 2-deoxynucleosides

1989-04-21

1990-05-29

Brown, Johnnie R.

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

Organic compounds

Carbohydrates or derivatives

536 24, C07H 19073, C07H 19173

Patent

active

049297236

ABSTRACT:
An O-, S-, or N-silyl- or O-, S-, or N-alkylpyrimidine is reacted with a protected 1-halo-, 1-alkoxy-, or 1-acyloxy-2-deoxy sugar in the presence of cuprous iodide and a halohydrocarbon solvent to prepare a nucleoside having an improved beta-anomer/alpha-anomer ratio. In a preferred embodiment of the invention, 2,4-bis(trimethylsilyloxy)-5-methylpyrimidine or 2,4-bis(trimethylsilyloxy)-5-ethylpyrimidine is reacted with 2-deoxy-3,5-di-O-p-toluyl-D-erythro-ribofuranosyl chloride in the presence of cuprous iodide and chloroform.

REFERENCES:
patent: 3748320 (1973-07-01), Vorbruggen et al.
patent: 4121037 (1978-10-01), Nakamura et al.
Nehring et al., Agnew Chem 82: 449 (1970).
Niedballa et al., J. of Org. Chem. 39, pp. 3654-3660 (1974).
Morrison et al., Organic Chemistry, Fourth Edition, Allyn and Bacon, Inc.; Boston, 1983, p. 1088.
Moore, Walter J., Physical Chemistry, Third Edition, Prentice-Hall, Inc.; Englewood Cliffs, N.J. 1962, pp. 309-311.

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