Oligoribonucleotide Synthesis. II. Preparation of 2′-<i>O</i>-tetrahydropyranyl Derivatives of Adenosine and Cytidine Necessary for Insertion in Stepwise Synthesis

DOI Web Site 被引用文献1件

書誌事項

公開日
1971-02-01
権利情報
  • http://www.nrcresearchpress.com/page/about/CorporateTextAndDataMining
DOI
  • 10.1139/v71-076
公開者
Canadian Science Publishing

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説明

<jats:p> The syntheses of N<jats:sup>6</jats:sup>-benzoyl-2′-O-tetrahydropyranyladenosine (2) and N<jats:sup>4</jats:sup>-benzoyl-2′-O-tetrahydropyranylcytidine (11) and their corresponding 5′-O-p-methoxytrityl derivatives, 3 and 12 respectively, are described. Compounds 2, 3, 11, and 12 are the protected derivatives of adenosine and cytidine required for insertion into a new oligoribonucleotide synthesis. Compound 2 was prepared from the known 2′-O-tetrahydropyranyladenosine by perbenzoylation followed by de-O-benzoylation. Compound 11 is prepared from cytidine by the following sequence: orthoacetate protection of the 2′- and 3′-hydroxyls; benzoylation of the 5′- and N<jats:sup>4</jats:sup>-positions; orthoacetate ring opening provided a mixture of the 2′- and 3′-monoacetates from which the major, 3′-O-acetyl-N<jats:sup>4</jats:sup>,5′-O-dibenzoylcytidine (7) was isolated; dihydropyran treatment on the 2′-hydroxyl of 7 and subsequent selective deacylation studies were carried out. Specific de-O-acylation gave 11. </jats:p>

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