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

Radiology

University of Texas Health Science Center at Houston

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
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

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10.1016/j.tet.2012.10.001

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@article{dc61c52cc4c249a1b5051f54b5b710af,

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.\}",

year = "2012",

month = dec,

day = "16",

doi = "10.1016/j.tet.2012.10.001",

language = "English",

volume = "68",

pages = "10326--10332",

journal = "Tetrahedron",

issn = "0040-4020",

number = "50",

}

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

TY - JOUR

T1 - An investigation on stereospecific fluorination at the 2′-arabino- position of a pyrimidine nucleoside

T2 - Radiosynthesis of 2′-deoxy-2′- [18F]fluoro-5-methyl-1-β-d-arabinofuranosyluracil

AU - Turkman, Nashaat

AU - Paolillo, Vincenzo

AU - Gelovani, Juri G.

AU - Alauddin, Mian M.

PY - 2012/12/16

Y1 - 2012/12/16

N2 - 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.

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.

KW - Fluorine-18

KW - PET

KW - Pyrimidine nucleoside

KW - Stereospecific fluorination

UR - https://www.scopus.com/pages/publications/84869093735

U2 - 10.1016/j.tet.2012.10.001

DO - 10.1016/j.tet.2012.10.001

M3 - Article

AN - SCOPUS:84869093735

SN - 0040-4020

VL - 68

SP - 10326

EP - 10332

JO - Tetrahedron

JF - Tetrahedron

IS - 50

ER -

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

Keywords

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