Synthesis of .beta.-l-2'-deoxy nucleosides

Details Synthesis of .beta.-l-2'-deoxy nucleosides Synthesis of .beta.-l-2'-deoxy nucleosides

C - Chemistry, Metallurgy

07

H

C07H 19/00 (2006.01)

Patent

CA 2531412

An improved process for the preparation of 2'-modified nucleosides and 2'- deoxy-nucleosides, such as, .beta.-L-2'-deoxy-thymidine (LdT), is provided. In particular, the improved process is directed to the synthesis of a 2'- deoxynucleoside that may utilize different starting materials but that proceeds via a chloro-sugar intermediate or via a 2,2'~ anhydro-1-furanosyl- nucleobase intermediate. Where an 2,2'-anhydro-1-furanosyl base intermediate is utilized, a reducing agent, such as Red-Al, and a sequestering agent, such as 15-crown-5 ether, that cause an intramolecular displacement reaction and formation of the desired nucleoside product in good yields are employed. An alternative process of the present invention utilizes a 2,2'-anhydro-1- furanosyl base intermediate without a sequestering agent to afford 2'- deoxynucleosides in good yields. The compounds made according to the present invention may be used as intermediates in the preparation of other nucleoside analogues, or may be used directly as antiviral and/or antineoplastic agents.

Cette invention concerne une technique améliorée de préparation de nucléosides modifiés en 2' et de nucléosides 2'-désoxy, tels que la .szlig.-L-2'-désoxy-thymidine (LdT). Cette technique concerne en particulier la synthèse d'un nucléoside 2'-désoxy qui peut utiliser différents matériaux de départ, mais qui se fait via un intermédiaire de chloro-sucre ou un intermédiaire d'une nucléobase de 2,2'- anhydro-1-furanosyle. Dans le cas d'un intermédiaire d'une base de 2,2'-anhydro-1-furanosyle, on utilise un agent réducteur tel que Red-Al, et un agent séquestrant tel qu'un éther15-couronne-5 qui provoquent une réaction de déplacement intramoléculaire et la formation abondante du produit nucléosidique recherché. En variante, on peut utiliser un intermédiaire de base 2,2'-anhydro-1-furanosyle sans agent séquestrant pour obtenir de bons rendements de 2'-désoxy nucléosides. Les composés obtenus selon la présente invention peuvent être utilisés comme intermédiaires pour l'obtention d'autres analogues de nucléosides, ou bien directement en tant qu'agents antiviraux et/ou anti-néoplasiques.

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