Electron-deficient benzotriazoles for the selective N-acetylation of nucleosides

Andrew K. Reid, C.J. McHugh, Graham Richie, D. Graham

Research output: Contribution to journalArticle

14 Citations (Scopus)

Abstract

The use of an acetylated benzotriazole for the selective protection of the amino groups of cytidine and 2′-deoxycytidine is reported. The use of the acetyl group is of considerable interest industrially in this role, and a single-step protection strategy advantageous in bulk production. 1-Acetyl-4-nitrobenzotriazole was found to readily acetylate the amine of cytidine preferentially over the exposed alcohol functionalities. With adaptation of the protocol, 2′-deoxycytidine was protected using the same reagent. A similar approach was attempted for the benzoylation of adenosine but was found to be unsuitable.
LanguageEnglish
Pages4201-4203
Number of pages2
JournalTetrahedron Letters
Volume47
Issue number25
DOIs
Publication statusPublished - 19 Jun 2006

Fingerprint

Acetylation
Cytidine
Deoxycytidine
Nucleosides
Electrons
Adenosine
Amines
Alcohols
benzotriazole
5-carboxy-methylaminomethyl-2'-O-methyluridine

Keywords

  • electron
  • benzotriazoles
  • N-acetylation
  • nucleosides

Cite this

Reid, Andrew K. ; McHugh, C.J. ; Richie, Graham ; Graham, D. / Electron-deficient benzotriazoles for the selective N-acetylation of nucleosides. In: Tetrahedron Letters. 2006 ; Vol. 47, No. 25. pp. 4201-4203.
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Electron-deficient benzotriazoles for the selective N-acetylation of nucleosides. / Reid, Andrew K.; McHugh, C.J.; Richie, Graham; Graham, D.

In: Tetrahedron Letters, Vol. 47, No. 25, 19.06.2006, p. 4201-4203.

Research output: Contribution to journalArticle

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T1 - Electron-deficient benzotriazoles for the selective N-acetylation of nucleosides

AU - Reid, Andrew K.

AU - McHugh, C.J.

AU - Richie, Graham

AU - Graham, D.

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KW - electron

KW - benzotriazoles

KW - N-acetylation

KW - nucleosides

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