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Name 5-Fluorodeoxyuridine;Doxifluridine;5-DFUR;Ro-21-9738;Furtulon
Chemical Name 5-Deoxy-5-fluorouridine
CAS 3094-09-5
Related CAS
Formula C9H11FN2O5
Structure
Formula Weight 246.19682
Stage 上市-1987
Company Chugai (Originator), Roche (Originator)
Activity/Mechanism Oncolytic Drugs, Apoptosis Inducers, Pyrimidine Antagonists, Thymidylate Synthase Inhibitors
Syn. Route 2
Route 1
the condensation of bis(trimethylsilyl)fluorouracil (i) with 5-deoxy-1,2,3-tri-o-acetyl-d-ribofuranose (ii) in the presence of trimethylsilyl trifluoromethanesulfonate (iii) gives the fully protected compound (iv), which is finally deprotected by the usual methods.
List of intermediates No.
4-chloro-5-(2-ethoxyethyl)-6-phenyl-2-pyrimidinylformamide (ii)
1-allyl 4-((2s,3r,6s,8r,9s)-3-butyl-2-([[tert-butyl(diphenyl)silyl]oxy]methyl)-8-[2-[(4-methoxybenzyl)oxy]ethyl]-9-methyl-1,7-dioxaspiro[5.5]undec-3-yl) succinate (i)
1-allyl 4-((2s,3r,6r,8r,9s)-3-butyl-2-([[tert-butyl(diphenyl)silyl]oxy]methyl)-8-[2-[(4-methoxybenzyl)oxy]ethyl]-9-methyl-1,7-dioxaspiro[5.5]undec-3-yl) succinate (iii)
1-allyl 4-((2r,3r,6s,8r,9s)-3-butyl-2-formyl-8-[2-[(4-methoxybenzyl)oxy]ethyl]-9-methyl-1,7-dioxaspiro[5.5]undec-3-yl) succinate (iv)
Reference 1:
    dsouza, r.; arnold, w.; van koeveringe, j.a.; kiss, j.; stereospecific synthesis of the anticancer agent 5-deoxy-5-fluorouridine (5-dfur) and its 5-deuterated derivatives. helv chim acta 1982, 65, 5, 1522.

Route 2
this compound can be prepared by several different ways:1) the reaction of 5-fluorouridine (i) with 2,2-dimethoxypropane (a) by means of p-toluenesulfonic acid gives 2,3-isopropylidene-5-fluorouridine (iii), which is treated with triphenylphosphite methiodide in dmf to afford 5-deoxy-5-iodo-2,3-isopropylidene-5-fluorouridine (iv). the reduction of (iv) with h2 over pd/c in methanol-triethyl-amine yields 5-deoxy-2,3-isopropylidene-5-fluorouridine (v), which is finally hydrolyzed with aqueous trifluoroacetic acid.2) the hydrolysis of compound (iv) with aqueous trifluoroacetic acid as before gives 5-deoxy-5-iodouridine (ii), which is finally reduced with h2 over pd/c as before.3) compound (ii) can also be obtained by reaction of (i) with triphenyl phosphite methiodide as before.4) it can also be prepared via reduction of the 5-chloro intermediate with tributyltin hydride.
List of intermediates No.
(2r,3s,4r,5r)-2-(hydroxymethyl)-5-[6-[[2-(methylsulfanyl)ethyl]amino]-2-[(3,3,3-trifluoropropyl)sulfanyl]-9h-purin-9-yl]tetrahydro-3,4-furandiol (a)
1,3-thiazolidine-2,4-dione (i)
5-(4-[[6-(methoxymethoxy)-2,5,7,8-tetramethyl-3,4-dihydro-2h-chromen-2-yl]methoxy]benzyl)-1,3-thiazolidine-2,4-dione (ii)
3-ethyl-7-methyl-3,7-diazabicyclo[3.3.1]nonan-9-one (iii)
3-ethyl-7-methyl-3,7-diazabicyclo[3.3.1]nonan-9-ol (iv)
3-ethyl-7-methyl-3,7-diazabicyclo[3.3.1]nonan-9-ol (v)
Reference 1:
    beranek, j.; hrebabecky, h.; analogs of nucleosides. xvi. 5-halo-2,3-sulfites in the synthesis of 2,5-dideoxy-5-fluorouridine and related analogs. coll czech chem commun 1978, 43, 15, 3268-78.
Reference 2:
    cook, a.f.; et al.; fluorinated pyrimidine nucleosides. 3. synthesis and antitumor activity of a series of 5-deoxy-5-fluoropyrimidine nucleosides. j med chem 1979, 22, 11, 1330-35.
Reference 3:
    cook, a.f. (hoffmann-la roche, inc.); 5-deoxy-5-fluoropyrimidine nucleosides. de 2756653; es 471584; fr 2374334; gb 1589688; jp 53095982; us 4071680 .
Reference 4:
    castaner, j.; albonico, s.m.; serradell, m.n.; blancafort, p.; doxifluridine. drugs fut 1981, 6, 2, 80.

来源:药化网

作者:药化小编

摘要:本文合成路线介绍的是药物中文名去氧氟尿苷;英文名5-Fluorodeoxyuridine;Doxifluridine;5-DFUR;Ro-21-9738;Furtulon;CAS[3094-09-5]

 
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