Reaction of Cytidine with Cyanopropargylic Alcohols: Synthesis of Functionalized Cytidine Cyclic Ketals

Valentina V. Nosyreva; Anastasiya G. Mal’kina; Olga G. Volostnykh; Alexander I. Albanov; Boris A. Trofimov

doi:10.1055/s-0033-1338539

Synthesis, Inhaltsverzeichnis

Synthesis 2013; 45(23): 3263-3268
DOI: 10.1055/s-0033-1338539

paper

Reaction of Cytidine with Cyanopropargylic Alcohols: Synthesis of Functionalized Cytidine Cyclic Ketals

Valentina V. Nosyreva

A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, 1 Favorsky Str., 664033 Irkutsk, Russian Federation Fax: +7(3952)419346 eMail: boris_trofimov@irioch.irk.ru

,

Anastasiya G. Mal’kina

A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, 1 Favorsky Str., 664033 Irkutsk, Russian Federation Fax: +7(3952)419346 eMail: boris_trofimov@irioch.irk.ru

,

Olga G. Volostnykh

A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, 1 Favorsky Str., 664033 Irkutsk, Russian Federation Fax: +7(3952)419346 eMail: boris_trofimov@irioch.irk.ru

,

Alexander I. Albanov

A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, 1 Favorsky Str., 664033 Irkutsk, Russian Federation Fax: +7(3952)419346 eMail: boris_trofimov@irioch.irk.ru

,

Boris A. Trofimov*

A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, 1 Favorsky Str., 664033 Irkutsk, Russian Federation Fax: +7(3952)419346 eMail: boris_trofimov@irioch.irk.ru

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Abstract

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Abstract

Cytidine reacts with one or two molecules of cyanopropargylic alcohols under mild conditions (K₂CO₃, DMF, 20–25 °C, 10–48 h) by the hydroxy groups of the ribose moiety to afford representatives of the two novel families of cytidine cyclic ketals. The first ones (53–76% yields) are formed with participation of the two vicinal hydroxyl groups (at 2′,3′-cis-positions) only. The second ones (7–21% yields) represent the adducts of cytidine with two molecules of cyanopropargylic alcohols involving all the three hydroxyl groups.

Key words

cytidine - cyanopropargylic alcohols - nucleophilic addition - cyclization - cyclic ketals

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