Acylation of pyrazofurin

Details Acylation of pyrazofurin Acylation of pyrazofurin

1976-02-23

1977-10-11

Moyer, Donald B.

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

Organic compounds

Carbohydrates or derivatives

C07D23138, C07D23140, C07H 706, C07H 1302

Patent

active

040536980

ABSTRACT:
A process for preparing new compounds which are N- and O-acylates of pyrazofurin comprises first selective mono-N-acylation under non-basic conditions in an organic solvent. The mono-N-acylate so formed is further acylated under mild basic conditions to provide a tetra-acylated or penta-acylated pyrazofurin derivative, depending upon the duration of reaction. Mild solvolysis of either a tetra-acylate or a penta-acylate provides a tri-acylated pyrazofurin derivative. In the presence of a strong base, the mono-N-acylate is further acylated to provide different tetra-acylates or penta-acylates of pyrazofurin, again depending upon the duration of reaction. Pyrazofurin acylates are useful as antiviral, antipsoriatic, and antifungal agents, as well as intermediates for new C-nucleosides.

REFERENCES:
gutcho, "Nucleotides and Nucleosides" (1970) published by Noyes Data Corp., N.J., pp. 5-15, 18, 19 & 174-178.

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