Stereoselective and Divergent Aza-Adenosine and Aza-Guanosine Syntheses from Xylofuranose, the Key Fragments of a STING Cyclic Dinucleotide Agonist.

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  • Additional Information
    • Source:
      Publisher: American Chemical Society Country of Publication: United States NLM ID: 2985193R Publication Model: Print-Electronic Cited Medium: Internet ISSN: 1520-6904 (Electronic) Linking ISSN: 00223263 NLM ISO Abbreviation: J Org Chem Subsets: MEDLINE
    • Publication Information:
      Publication: Columbus Oh : American Chemical Society
      Original Publication: Easton, Pa. [etc.]
    • Subject Terms:
      Adenosine* ; Nucleosides*; Guanosine
    • Abstract:
      The stereoselective and divergent synthesis of two aza-nucleosides is reported. Starting from xylofuranose 9 , aza-adenosine 2 was prepared in 13 steps and 7% overall yield, and aza-guanosine 3 was prepared in 13 steps and 7.8% overall yield. Compared to the original syntheses, some advantages of these new routes are significant yield improvement, overall step-count reduction, an optimized protecting group strategy, the development of a versatile platform for nitrogenous base incorporation, and the elimination of hazardous reagents (e.g., benzyl isocyanate, Et 3 N·HF).
    • Accession Number:
      0 (Nucleosides)
      12133JR80S (Guanosine)
      K72T3FS567 (Adenosine)
    • Publication Date:
      Date Created: 20210714 Date Completed: 20220221 Latest Revision: 20220221
    • Publication Date:
      20231215
    • Accession Number:
      10.1021/acs.joc.1c00984
    • Accession Number:
      34259509