168787-13-1Relevant academic research and scientific papers
Synthesis of hydantoin analogues of 3'-fluoro-3'-deoxythymidine (FLT)
Abdel-Bary, Hamed M.,El-Barbary, Ahmed A.,Khodair, Ahmed I.,Megied, Ahmed Es Abdel,Pedersen, Erik B.,Nielsen, Claus
, p. 149 - 155 (2007/10/02)
Reaction of methyl 2-deoxy-5-O-(4-phenylbenzoyl)-β-D-erythro-pentofuranoside 2 with diethylaminosulfur trifluoride (DAST) in a 1:10 molar ratio in CH2Cl2 at room temperature for 5 d afforded methyl 2,3-dideoxy-3-fluoro-5-O-(4-phenylbenzoyl)-β-D-erythro-pentafuranoside 4 in 57percent yield, while the α-anomer 3 under the same reaction conditions yielded the 3-fluoro-α-D-erythro derivative 10 in 14percent yield together with the 5-fluoro-D-α--threo derivative 11 in 22percent yield. (Z)-5-Benzylidene-, (E)-ethylidene- and 5,5-dimethylhydantoin nucleosides were obtained by condensation of the appropriate silylated nucleobases with 4.The protected nucleosides were in all cases deblocked by treatment with sodium methoxide in methanol.The (Z)-ethylidene group isomerized to the E configuration during the nucleoside synthesis. - Key words: hydantoin / 3'-fluoro-3'-deoxythymidine / methyl 2,3-dideoxy-3-fluoro-β-D-erythro-pentofuranoside
