Stereospecific fluorination of 1,3,5-tri-O-benzoyl-α-D-ribofuranose-2-sulfonate esters: Preparation of a versatile intermediate for synthesis of 2′-[ 18F ]-fluoro-arabinonucleosides

Mian M. Alauddin; Peter S. Conti; Thomas Mathew; John D. Fissekis; G. K. Surya Prakash; Kyoichi A. Watanabe

doi:10.1016/S0022-1139(00)00307-9

Stereospecific fluorination of 1,3,5-tri-O-benzoyl-α-D-ribofuranose-2-sulfonate esters: Preparation of a versatile intermediate for synthesis of 2′-[ ¹⁸F ]-fluoro-arabinonucleosides

Mian M. Alauddin, Peter S. Conti, Thomas Mathew, John D. Fissekis, G. K. Surya Prakash, Kyoichi A. Watanabe

Cancer Systems Imaging

Research output: Contribution to journal › Article › peer-review

23 Scopus citations

Abstract

A detailed investigation on fluorination of 1,3,5-tri-O-benzoyl-α-D-ribofuranose-2-sulphonate esters is reported. Various combinations of sulfonate esters, fluorinating agents and solvents were evaluated in this study. Organic ammonium fluoride, in particular n-Bu₄NF, was found to be better fluorinating agent than inorganic fluoride, and 1,3,5-tri-O-benzoyl-α-D-ribofuranose-2-trifluoromethylsulphonate ester appeared to be the best substrate. The developed method is suitable for stereospecific (arabino) incorporation of radiofluorine (¹⁸F) into the sugar moiety.

Original language	English (US)
Pages (from-to)	87-91
Number of pages	5
Journal	Journal of Fluorine Chemistry
Volume	106
Issue number	1
DOIs	https://doi.org/10.1016/S0022-1139(00)00307-9
State	Published - Oct 2000

Keywords

Fluorination
N-BuNF
Nucleophilic radiofluorine

ASJC Scopus subject areas

Biochemistry
Environmental Chemistry
Physical and Theoretical Chemistry
Organic Chemistry
Inorganic Chemistry

Access to Document

10.1016/S0022-1139(00)00307-9

Cite this

Alauddin, M. M., Conti, P. S., Mathew, T., Fissekis, J. D., Surya Prakash, G. K., & Watanabe, K. A. (2000). Stereospecific fluorination of 1,3,5-tri-O-benzoyl-α-D-ribofuranose-2-sulfonate esters: Preparation of a versatile intermediate for synthesis of 2′-[ ¹⁸F ]-fluoro-arabinonucleosides. Journal of Fluorine Chemistry, 106(1), 87-91. https://doi.org/10.1016/S0022-1139(00)00307-9

Stereospecific fluorination of 1,3,5-tri-O-benzoyl-α-D-ribofuranose-2-sulfonate esters: Preparation of a versatile intermediate for synthesis of 2′-[ ¹⁸F ]-fluoro-arabinonucleosides. / Alauddin, Mian M.; Conti, Peter S.; Mathew, Thomas et al.
In: Journal of Fluorine Chemistry, Vol. 106, No. 1, 10.2000, p. 87-91.

Research output: Contribution to journal › Article › peer-review

Alauddin, MM, Conti, PS, Mathew, T, Fissekis, JD, Surya Prakash, GK & Watanabe, KA 2000, 'Stereospecific fluorination of 1,3,5-tri-O-benzoyl-α-D-ribofuranose-2-sulfonate esters: Preparation of a versatile intermediate for synthesis of 2′-[ ¹⁸F ]-fluoro-arabinonucleosides', Journal of Fluorine Chemistry, vol. 106, no. 1, pp. 87-91. https://doi.org/10.1016/S0022-1139(00)00307-9

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title = "Stereospecific fluorination of 1,3,5-tri-O-benzoyl-α-D-ribofuranose-2-sulfonate esters: Preparation of a versatile intermediate for synthesis of 2′-[ 18F ]-fluoro-arabinonucleosides",

abstract = "A detailed investigation on fluorination of 1,3,5-tri-O-benzoyl-α-D-ribofuranose-2-sulphonate esters is reported. Various combinations of sulfonate esters, fluorinating agents and solvents were evaluated in this study. Organic ammonium fluoride, in particular n-Bu4NF, was found to be better fluorinating agent than inorganic fluoride, and 1,3,5-tri-O-benzoyl-α-D-ribofuranose-2-trifluoromethylsulphonate ester appeared to be the best substrate. The developed method is suitable for stereospecific (arabino) incorporation of radiofluorine (18F) into the sugar moiety.",

keywords = "Fluorination, N-BuNF, Nucleophilic radiofluorine",

author = "Alauddin, {Mian M.} and Conti, {Peter S.} and Thomas Mathew and Fissekis, {John D.} and {Surya Prakash}, {G. K.} and Watanabe, {Kyoichi A.}",

note = "Funding Information: The authors wish to thank Mr. Allan D. Kershaw for assisting with the NMR spectra. This work was supported by the National Cancer Institute Grant CA 72896. ",

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AU - Alauddin, Mian M.

AU - Conti, Peter S.

AU - Mathew, Thomas

AU - Fissekis, John D.

AU - Surya Prakash, G. K.

AU - Watanabe, Kyoichi A.

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KW - Fluorination

KW - N-BuNF

KW - Nucleophilic radiofluorine

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