Simplified synthesis of 2′-O-alkyl ribopyrimidines

Richard P. Hodge, Nanda D. Sinha

Research output: Contribution to journalArticle

17 Citations (Scopus)

Abstract

Direct 2′-hydroxyl alkylation (R = methyl, ethyl, propyl, pentyl or allyl) of 5′-dimethoxytrityl-N-(t-butylphenoxyacetyl or benzoyl)-cytidine 1 was achieved by reaction in the presence of silver I oxide and a catalytic amount of pyridine with excess alkyl halide. At 0°C alkylation of the 2′-hydroxyl was found to be highly selective; less than 10% di (2′3′)-O-alkylated or 3′-O-alkylated side products were detected in most cases. Quantitative deamination of 2′-O-alkylated cytidines to 2′-O-alkylated uridines were performed by refluxing in 4M aq. LiOH solution. This method simplifies access to various 2′-O-alkylated ribopyrimidines using readily available starting materials in one or two steps.

Original languageEnglish (US)
Pages (from-to)2933-2936
Number of pages4
JournalTetrahedron Letters
Volume36
Issue number17
DOIs
StatePublished - Apr 24 1995
Externally publishedYes

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Cytidine
Alkylation
Hydroxyl Radical
Deamination
Uridine
Silver
Oxides
pyridine
disilver oxide

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Simplified synthesis of 2′-O-alkyl ribopyrimidines. / Hodge, Richard P.; Sinha, Nanda D.

In: Tetrahedron Letters, Vol. 36, No. 17, 24.04.1995, p. 2933-2936.

Research output: Contribution to journalArticle

Hodge, Richard P. ; Sinha, Nanda D. / Simplified synthesis of 2′-O-alkyl ribopyrimidines. In: Tetrahedron Letters. 1995 ; Vol. 36, No. 17. pp. 2933-2936.
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