Process for preparing 2'-cyano pyrimidine nucleoside compounds

Details Process for preparing 2'-cyano pyrimidine nucleoside compounds Process for preparing 2'-cyano pyrimidine nucleoside compounds

1995-06-01

1997-08-05

Wilson, James O.

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

Organic compounds

Carbohydrates or derivatives

536 281, 536 282, 536 284, 536 285, 536 2852, 536 2853, 536 2854, C07H 1906, C07H 1909

Patent

active

056544200

ABSTRACT:
A process for preparing a compound of the formula: ##STR1## wherein R.sup.1 is a hydroxyl or an amino which may optionally be substituted; R.sup.2 is a hydrogen or a C.sub.1 -C.sub.4 alkyl; and R.sup.4a and R.sup.5a together represent a group of the formula: --R.sup.6 R.sup.7 Si--O--SiR.sup.6' R.sup.7', wherein R.sup.6, R.sup.7, R.sup.6' and R.sup.7' are the same or different and each is a C.sub.1 -C.sub.4 alkyl, which process comprises reacting a reducing agent and a cyanolating agent with a compound of the formula: ##STR2## wherein R.sup.9 is an alkoxythiocarbonyl having a C.sub.1 -C.sub.4 alkyl or an arylthiocarbonyl having a C.sub.6 -C.sub.10 aryl.

REFERENCES:
Dieter Habich, et al, "Synthesis of 3'-Cyano-3'-deoxy-.beta.-D-arabino-nucleosides", 1988, pp. 943-947, Synthesis.
Dong Yu et al, "Synthesis of 3'-Cyano-2', 3'-dideoyadenosine and 2', 3'-Dideoxy-3'-formyladenosine", 1989, pp. 3240-3342, J. Org. Chem.
Matsuda et al, Chemical Abstracts, "Synthesis of a New Patent Antitumor Nucleoside-2'-C-cyano-2'-deoxy-1-.beta.-D-arabinofuransyl-cytosine", 115 (3): 29817a (1991).
A. Matsuda et al, "Nucleosides and Nucleotides. 100.2'-C-Cyano-2'-deoxy-1-.beta.-D-arabinofuransyl-cytosine (CNDAE): Design of a Potential Mechanism-Based DNA-Srrand Breaking Antineoplastic Nucleoside", J. Med. Chem., vol. 34 (9), 2917-2919, Sep. 1991.
T. Beardsley, "A War Not Won", Scientific American, (Jan. 1994), vol. 270, No. 1, 130-138.

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