The synthesis of gemcitabine
The synthesis of gemcitabine
Gemcitabine is a fluorinated nucleoside currently administered against a number of cancers. It consists of a cytosine base and a 2-deoxy-2,2-difluororibose sugar. The synthetic challenges associated with the introduction of the fluorine atoms, as well as with nucleobase introduction of 2,2-difluorinated sugars, combined with the requirement to have an efficient process suitable for large scale synthesis, have spurred significant activity towards the synthesis of gemcitabine exploring a wide variety of synthetic approaches. In addition, many methods have been developed for selective crystallisation of diastereomeric (including anomeric) mixtures. In that regard, the 2-deoxy-2,2-difluororibose sugar is one of the most investigated fluorinated carbohydrates in terms of its synthesis. The versatility of synthetic methods employed is illustrative of the current state of the art of fluorination methodology for the synthesis of CF2-containing carbohydrates, and involves the use of fluorinated building blocks, as well as nucleophilic and electrophilic fluorination of sugar precursors.
gemcitabine, fluorinated nucleoside, fluorosugar, fluorination, nucleobase introduction
59-73
Brown, Kylie
feabbf9e-76ff-4d6e-9ec1-1c14507bfa59
Dixey, Michael
8922b06c-46d9-4eaf-9baf-dcde71e9d64e
Weymouth-Wilson, Alex
a25a6ccc-864f-45be-bbd3-016286c5f563
Linclau, Bruno
19b9cacd-b8e8-4c65-af36-6352cade84ba
31 March 2014
Brown, Kylie
feabbf9e-76ff-4d6e-9ec1-1c14507bfa59
Dixey, Michael
8922b06c-46d9-4eaf-9baf-dcde71e9d64e
Weymouth-Wilson, Alex
a25a6ccc-864f-45be-bbd3-016286c5f563
Linclau, Bruno
19b9cacd-b8e8-4c65-af36-6352cade84ba
Brown, Kylie, Dixey, Michael, Weymouth-Wilson, Alex and Linclau, Bruno
(2014)
The synthesis of gemcitabine.
Carbohydrate Research, 387, .
(doi:10.1016/j.carres.2014.01.024).
Abstract
Gemcitabine is a fluorinated nucleoside currently administered against a number of cancers. It consists of a cytosine base and a 2-deoxy-2,2-difluororibose sugar. The synthetic challenges associated with the introduction of the fluorine atoms, as well as with nucleobase introduction of 2,2-difluorinated sugars, combined with the requirement to have an efficient process suitable for large scale synthesis, have spurred significant activity towards the synthesis of gemcitabine exploring a wide variety of synthetic approaches. In addition, many methods have been developed for selective crystallisation of diastereomeric (including anomeric) mixtures. In that regard, the 2-deoxy-2,2-difluororibose sugar is one of the most investigated fluorinated carbohydrates in terms of its synthesis. The versatility of synthetic methods employed is illustrative of the current state of the art of fluorination methodology for the synthesis of CF2-containing carbohydrates, and involves the use of fluorinated building blocks, as well as nucleophilic and electrophilic fluorination of sugar precursors.
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e-pub ahead of print date: 10 February 2014
Published date: 31 March 2014
Keywords:
gemcitabine, fluorinated nucleoside, fluorosugar, fluorination, nucleobase introduction
Identifiers
Local EPrints ID: 362690
URI: http://eprints.soton.ac.uk/id/eprint/362690
ISSN: 0008-6215
PURE UUID: 1be100f9-3f93-4544-8e48-fb50a570aa54
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Date deposited: 03 Mar 2014 16:28
Last modified: 15 Mar 2024 03:05
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Author:
Kylie Brown
Author:
Michael Dixey
Author:
Alex Weymouth-Wilson
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