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A linear synthesis of gemcitabine

A linear synthesis of gemcitabine
A linear synthesis of gemcitabine
Gemcitabine, 2’-deoxy-2’,2’-difluorocytidine, is currently prescribed against a number of cancers. Here we report a linear synthesis of gemcitabine with a high-yielding direct conversion of 3,5-di-O-benzoyl-2-deoxy-2,2-difluororibose into the corresponding glycosyl urea as the key step, followed by conventional conversion to the cytosine base via the uracil derivative. The process proceeded with modest anomeric selectivity.
gemcitabine, glycosyl urea, fluorinated nucleoside, linear nucleoside introduction
0008-6215
71-75
Brown, Kylie
feabbf9e-76ff-4d6e-9ec1-1c14507bfa59
Weymouth-Wilson, Alex
a25a6ccc-864f-45be-bbd3-016286c5f563
Linclau, Bruno
19b9cacd-b8e8-4c65-af36-6352cade84ba
Brown, Kylie
feabbf9e-76ff-4d6e-9ec1-1c14507bfa59
Weymouth-Wilson, Alex
a25a6ccc-864f-45be-bbd3-016286c5f563
Linclau, Bruno
19b9cacd-b8e8-4c65-af36-6352cade84ba

Brown, Kylie, Weymouth-Wilson, Alex and Linclau, Bruno (2015) A linear synthesis of gemcitabine. Carbohydrate Research, 406, 71-75. (doi:10.1016/j.carres.2015.01.001).

Record type: Article

Abstract

Gemcitabine, 2’-deoxy-2’,2’-difluorocytidine, is currently prescribed against a number of cancers. Here we report a linear synthesis of gemcitabine with a high-yielding direct conversion of 3,5-di-O-benzoyl-2-deoxy-2,2-difluororibose into the corresponding glycosyl urea as the key step, followed by conventional conversion to the cytosine base via the uracil derivative. The process proceeded with modest anomeric selectivity.

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Accepted/In Press date: 6 January 2015
Published date: 14 January 2015
Keywords: gemcitabine, glycosyl urea, fluorinated nucleoside, linear nucleoside introduction

Identifiers

Local EPrints ID: 373347
URI: https://eprints.soton.ac.uk/id/eprint/373347
ISSN: 0008-6215
PURE UUID: ae83c572-6b16-46e9-9a3c-8c9ffc947902
ORCID for Bruno Linclau: ORCID iD orcid.org/0000-0001-8762-0170

Catalogue record

Date deposited: 15 Jan 2015 16:45
Last modified: 31 Jul 2019 00:46

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