An investigation on stereospecific fluorination at the 2′-arabino- position of a pyrimidine nucleoside: Radiosynthesis of 2′-deoxy-2′- [18F]fluoro-5-methyl-1-β-d-arabinofuranosyluracil

Nashaat Turkman; Vincenzo Paolillo; Juri G. Gelovani; Mian M. Alauddin

doi:10.1016/j.tet.2012.10.001

An investigation on stereospecific fluorination at the 2′-arabino- position of a pyrimidine nucleoside: Radiosynthesis of 2′-deoxy-2′- [¹⁸F]fluoro-5-methyl-1-β-d-arabinofuranosyluracil

Nashaat Turkman, Vincenzo Paolillo, Juri G. Gelovani, Mian M. Alauddin

Cancer Systems Imaging

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

3 Scopus citations

Abstract

Direct fluorination at the 2′-arabino-position of a pyrimidine nucleoside has been a long-standing challenge, yet we recently reported such a stereospecific fluorination for the first time in the synthesis of [ ¹⁸F]FMAU, albeit in low yields. Herein we report the results of an investigation on stereospecific fluorination on a variety of precursors for synthesis of [¹⁸F]FMAU. Several precursors were synthesized in multiple steps and fluorination was performed at the 2′-arabino-position using K[¹⁸F]/kryptofix 2.2.2. All precursors produced [ ¹⁸F]FMAU in low yields.

Original language	English (US)
Pages (from-to)	10326-10332
Number of pages	7
Journal	Tetrahedron
Volume	68
Issue number	50
DOIs	https://doi.org/10.1016/j.tet.2012.10.001
State	Published - Dec 16 2012

Keywords

Fluorine-18
PET
Pyrimidine nucleoside
Stereospecific fluorination

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

Access to Document

10.1016/j.tet.2012.10.001

Cite this

An investigation on stereospecific fluorination at the 2′-arabino- position of a pyrimidine nucleoside: Radiosynthesis of 2′-deoxy-2′- [¹⁸F]fluoro-5-methyl-1-β-d-arabinofuranosyluracil. / Turkman, Nashaat; Paolillo, Vincenzo; Gelovani, Juri G. et al.
In: Tetrahedron, Vol. 68, No. 50, 16.12.2012, p. 10326-10332.

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

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title = "An investigation on stereospecific fluorination at the 2′-arabino- position of a pyrimidine nucleoside: Radiosynthesis of 2′-deoxy-2′- [18F]fluoro-5-methyl-1-β-d-arabinofuranosyluracil",

abstract = "Direct fluorination at the 2′-arabino-position of a pyrimidine nucleoside has been a long-standing challenge, yet we recently reported such a stereospecific fluorination for the first time in the synthesis of [ 18F]FMAU, albeit in low yields. Herein we report the results of an investigation on stereospecific fluorination on a variety of precursors for synthesis of [18F]FMAU. Several precursors were synthesized in multiple steps and fluorination was performed at the 2′-arabino-position using K[18F]/kryptofix 2.2.2. All precursors produced [ 18F]FMAU in low yields.",

keywords = "Fluorine-18, PET, Pyrimidine nucleoside, Stereospecific fluorination",

author = "Nashaat Turkman and Vincenzo Paolillo and Gelovani, {Juri G.} and Alauddin, {Mian M.}",

note = "Funding Information: This work was supported by the Small Animal Imaging Core facility Grant ; U24 CA126577-01 , NIH/NCI , and the NCI CCSG Core Grant CA 106672-36 .",

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AU - Paolillo, Vincenzo

AU - Gelovani, Juri G.

AU - Alauddin, Mian M.

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AB - Direct fluorination at the 2′-arabino-position of a pyrimidine nucleoside has been a long-standing challenge, yet we recently reported such a stereospecific fluorination for the first time in the synthesis of [ 18F]FMAU, albeit in low yields. Herein we report the results of an investigation on stereospecific fluorination on a variety of precursors for synthesis of [18F]FMAU. Several precursors were synthesized in multiple steps and fluorination was performed at the 2′-arabino-position using K[18F]/kryptofix 2.2.2. All precursors produced [ 18F]FMAU in low yields.

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