title: A linear synthesis of gemcitabine.
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.
authors: Chemistry, University of Southampton, Highfield, Southampton SO17 1BJ, UK; Dextra Laboratories Ltd, The Science and Technology Centre, Earley Gate, Whiteknights Road, Reading RG6 6BZ, UK.
authors: Kylie
authors: K
authors: Brown
authors: Dextra Laboratories Ltd, The Science and Technology Centre, Earley Gate, Whiteknights Road, Reading RG6 6BZ, UK.
authors: Alex
authors: A
authors: Weymouth-Wilson
authors: Chemistry, University of Southampton, Highfield, Southampton SO17 1BJ, UK. Electronic address: bruno.linclau@soton.ac.uk.
authors: Bruno
authors: B
authors: Linclau
mesh_terms: D000215:Acylation; D000964:Antimetabolites, Antineoplastic / Q000138:chemical synthesis*; D002384:Catalysis; D003500:Cyclization; D003841:Deoxycytidine / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D014508:Urea / Q000737:chemistry; D000093542:Gemcitabine
chemical_list: D000964:Antimetabolites, Antineoplastic; D003841:Deoxycytidine; D014508:Urea; D000093542:Gemcitabine
keywords: Fluorinated nucleoside; Gemcitabine; Glycosyl urea; Linear nucleoside introduction