Transient Protection. 2. One-Flask Synthesis of 6- O -[ (4-Nitrophenyl)ethyl]-2‘-deoxyguanosine Nucleosides

Xiaolian Gao, Barbara L. Gaffney, Susan Hadden, Roger A. Jones

Research output: Contribution to journalArticlepeer-review

26 Scopus citations

Abstract

Transient protection of both the 3’- and 5’-hydroxyl groups of la or of the 3’-hydroxyl group of lb, followed by Mitsunobu alkylation with 2-(4-nitrophenyl)ethanol gave the 06-protected nucleosides 4a or 4b in good yield in a one-flask procedure. Similar reactions with 3-hydroxypropionitrile or 2-(phenylsulfonyl) ethanol, however, were unsuccessful. Reaction of lb without 3’-hydroxyl protection led to formation of a stable N3 → 3’ cyclonucleoside, 7a.

Original languageEnglish (US)
Pages (from-to)755-758
Number of pages4
JournalJournal of Organic Chemistry
Volume51
Issue number5
DOIs
StatePublished - 1986

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

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