Utilization of tetrabutylammonium triphenyldifluorosilicate (TBAT) in the synthesis of 6-fluoropurine nucleosides

Vadim Gurvich, Hye Young Kim, Richard P. Hodge, Constance M. Harris, Thomas M. Harris

Research output: Contribution to journalArticle

10 Citations (Scopus)

Abstract

Tetrabutylammonium triphenydifluorosilicate (TBAT) has been found to be a useful reagent for the conversion of 6-chloropurine nucleosides to 6- fluoropurine derivatives. The 6-chloropurine nucleosides were reacted with trimethylamine to form quaternary trimethylammonium salts which were treated in situ with TBAT in DMF to effect conversion to the 6-fluoro derivatives in yields of 59-72%.

Original languageEnglish (US)
Pages (from-to)2327-2333
Number of pages7
JournalNucleosides and Nucleotides
Volume18
Issue number10
StatePublished - 1999
Externally publishedYes

Fingerprint

Nucleosides
Derivatives
Salts
6-fluoropurine
6-chloropurine
tetrabutylammonium triphenyldifluorosilicate
tetrabutylammonium
trimethylamine

ASJC Scopus subject areas

  • Biochemistry
  • Genetics

Cite this

Gurvich, V., Kim, H. Y., Hodge, R. P., Harris, C. M., & Harris, T. M. (1999). Utilization of tetrabutylammonium triphenyldifluorosilicate (TBAT) in the synthesis of 6-fluoropurine nucleosides. Nucleosides and Nucleotides, 18(10), 2327-2333.

Utilization of tetrabutylammonium triphenyldifluorosilicate (TBAT) in the synthesis of 6-fluoropurine nucleosides. / Gurvich, Vadim; Kim, Hye Young; Hodge, Richard P.; Harris, Constance M.; Harris, Thomas M.

In: Nucleosides and Nucleotides, Vol. 18, No. 10, 1999, p. 2327-2333.

Research output: Contribution to journalArticle

Gurvich, V, Kim, HY, Hodge, RP, Harris, CM & Harris, TM 1999, 'Utilization of tetrabutylammonium triphenyldifluorosilicate (TBAT) in the synthesis of 6-fluoropurine nucleosides', Nucleosides and Nucleotides, vol. 18, no. 10, pp. 2327-2333.
Gurvich, Vadim ; Kim, Hye Young ; Hodge, Richard P. ; Harris, Constance M. ; Harris, Thomas M. / Utilization of tetrabutylammonium triphenyldifluorosilicate (TBAT) in the synthesis of 6-fluoropurine nucleosides. In: Nucleosides and Nucleotides. 1999 ; Vol. 18, No. 10. pp. 2327-2333.
@article{0a7d41d84b1e4c9f856ee5a09d660fcf,
title = "Utilization of tetrabutylammonium triphenyldifluorosilicate (TBAT) in the synthesis of 6-fluoropurine nucleosides",
abstract = "Tetrabutylammonium triphenydifluorosilicate (TBAT) has been found to be a useful reagent for the conversion of 6-chloropurine nucleosides to 6- fluoropurine derivatives. The 6-chloropurine nucleosides were reacted with trimethylamine to form quaternary trimethylammonium salts which were treated in situ with TBAT in DMF to effect conversion to the 6-fluoro derivatives in yields of 59-72{\%}.",
author = "Vadim Gurvich and Kim, {Hye Young} and Hodge, {Richard P.} and Harris, {Constance M.} and Harris, {Thomas M.}",
year = "1999",
language = "English (US)",
volume = "18",
pages = "2327--2333",
journal = "Nucleosides, Nucleotides and Nucleic Acids",
issn = "1525-7770",
publisher = "Marcel Dekker Inc.",
number = "10",

}

TY - JOUR

T1 - Utilization of tetrabutylammonium triphenyldifluorosilicate (TBAT) in the synthesis of 6-fluoropurine nucleosides

AU - Gurvich, Vadim

AU - Kim, Hye Young

AU - Hodge, Richard P.

AU - Harris, Constance M.

AU - Harris, Thomas M.

PY - 1999

Y1 - 1999

N2 - Tetrabutylammonium triphenydifluorosilicate (TBAT) has been found to be a useful reagent for the conversion of 6-chloropurine nucleosides to 6- fluoropurine derivatives. The 6-chloropurine nucleosides were reacted with trimethylamine to form quaternary trimethylammonium salts which were treated in situ with TBAT in DMF to effect conversion to the 6-fluoro derivatives in yields of 59-72%.

AB - Tetrabutylammonium triphenydifluorosilicate (TBAT) has been found to be a useful reagent for the conversion of 6-chloropurine nucleosides to 6- fluoropurine derivatives. The 6-chloropurine nucleosides were reacted with trimethylamine to form quaternary trimethylammonium salts which were treated in situ with TBAT in DMF to effect conversion to the 6-fluoro derivatives in yields of 59-72%.

UR - http://www.scopus.com/inward/record.url?scp=0032695350&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0032695350&partnerID=8YFLogxK

M3 - Article

VL - 18

SP - 2327

EP - 2333

JO - Nucleosides, Nucleotides and Nucleic Acids

JF - Nucleosides, Nucleotides and Nucleic Acids

SN - 1525-7770

IS - 10

ER -