Synthesis of 1- and 1,2,2′-Deuteriated Deoxyribose and Incorporation into Deoxyribonucleosides

Richard P. Hodge, Charles K. Brush, Constance M. Harris, Thomas M. Harris

    Research output: Contribution to journalArticle

    40 Scopus citations

    Abstract

    Thymidine, deoxycytidine, deoxyadenosine, and deoxyguanosine have been prepared with deuterium substitution at position 1′ and at positions 1′, 2′, and 2″ from deuteriated deoxyribose. The synthetic strategy involved reduction of the bis(tert-butyldimethylsilyl) derivative 4a of 2-deoxyribonolactone (3a) with Dibal-D followed by deprotection (HCl/MeOH and tetrabutylammonium fluoride) to give 1-deuterio methyl glycoside 7a which was converted to the 1-deuterio 3,5-ditoluoyl methyl glycoside 8a. Preliminary exchange of 2-deoxyribonolactone with NaOMe/MeOD brought about 2,2′-dideuteriation; treatment as above gave the 1,2,2′-trideuterio 3,5-ditoluoyl methyl glycoside 8b. 8a and 8b were condensed with heterocyclic bases via α-chloro derivatives 9a and 9b to form deoxynucleosides. New methods were utilized for preparation of deoxycytidine and deoxyguanosine which are improvements over published procedures.

    Original languageEnglish (US)
    Pages (from-to)1553-1564
    Number of pages12
    JournalJournal of Organic Chemistry
    Volume56
    Issue number4
    DOIs
    StatePublished - Feb 1 1991

    ASJC Scopus subject areas

    • Organic Chemistry

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