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- Title
Sustainable Protocol for the Synthesis of 2′,3′-Dideoxynucleoside and 2′,3′-Didehydro-2′,3′-dideoxynucleoside Derivatives.
- Authors
Martín-Nieves, Virginia; Sanghvi, Yogesh S.; Fernández, Susana; Ferrero, Miguel
- Abstract
An improved protocol for the transformation of ribonucleosides into 2′,3′-dideoxynucleoside and 2′,3′-didehydro-2′,3′-dideoxynucleoside derivatives, including the anti-HIV drugs stavudine (d4T), zalcitabine (ddC) and didanosine (ddI), was established. The process involves radical deoxygenation of xanthate using environmentally friendly and low-cost reagents. Bromoethane or 3-bromopropanenitrile was the alkylating agent of choice to prepare the ribonucleoside 2′,3′-bisxanthates. In the subsequent radical deoxygenation reaction, tris(trimethylsilyl)silane and 1,1′-azobis(cyclohexanecarbonitrile) were used to replace hazardous Bu3SnH and AIBN, respectively. In addition, TBAF was substituted for camphorsulfonic acid in the deprotection step of the 5′-O-silyl ether group, and an enzyme (adenosine deaminase) was used to transform 2′,3′-dideoxyadenosine into 2′,3′-dideoxyinosine (ddI) in excellent yield.
- Subjects
ANTI-HIV agents; ADENOSINE deaminase; ALKYLATING agents; RIBONUCLEOSIDES; DEOXYGENATION; SILYL ethers; TENOFOVIR
- Publication
Molecules, 2022, Vol 27, Issue 13, p3993
- ISSN
1420-3049
- Publication type
Article
- DOI
10.3390/molecules27133993