22423-25-2Relevant academic research and scientific papers
Synthesis of beta-L-2'-deoxy nucleosides
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Page/Page column 43; 44, (2010/02/11)
An improved process for the preparation of 2′-modified nucleosides and 2′-deoxy-nucleosides, such as, β-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.
Synthesis of 2'-Azido-2',3'-didehydro-2',3'-dideoxythymidine
Mikhailopulo, Igor A.,Zaitseva, Galina V.,Vaaks, Elena V.,Balzarini, Jan,Clercq, Eric De,et al.
, p. 513 - 520 (2007/10/02)
Compound 15 - the 2'-azido analog of the anti-HIV compound 2',3'-didehydro-2',3'-dideoxythymidine - was synthesized.Treatment of 5'-O-trityl-β-D-ribofuranosylthymine (1) with DAST or MSTF gave the 2,2'-anhydro derivative 2.The latter and its 3'-O-benzoate
