3'-Deoxy-3'-fluorothymidine supplier

Name
3'-Deoxy-3'-fluorothymidine
EINECS
CAS No. 25526-93-6
Article Data26
CAS DataBase
Density 1.44 g/cm³
Solubility
Melting Point 176-178 °C(lit.)
Formula C₁₀H₁₃FN₂O₄
Boiling Point
Molecular Weight 244.223
Flash Point
Transport Information
Appearance Colourless solid
Safety 24/25
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms 1-(3'-Deoxy-3'-fluoro-b-D-pentofuranosyl)thymine;3'-Deoxy-3'-fluorothymidine;3'-Fluoro-3'-deoxythymidine;3'-Fluorodeoxythymidine;3'-Fluorothymidine;Alovudine;CL 184824;FLT;MIV 310;NSC 140025;thymidine, 3'-deoxy-3'-fluoro-;1-[(2R,4S,5R)-4-fluoro-5-(hydroxymethyl)oxolan-2-yl]-5-methylpyrimidine-2,4-dione;
PSA 84.32000
LogP -0.53710

Synthetic route

: 5'-O-(4,4'-dimethoxytrityl)-3'-deoxy-3'-fluorothymidine

: 25526-93-6
alovudine

Conditions

Conditions	Yield
With hydrogenchloride In acetonitrile at 45℃; for 0.166667h;	97%
With hydrogenchloride In water; dimethyl sulfoxide at 175℃; for 0.0166667h;
With hydrogenchloride In acetonitrile

: 145688-92-2
1-(2,3-dideoxy-3-fluoro-β-D-erythro-pentofuranosyl)-4-methoxy-5-methyl-2(1H)-pyrimidinone

: 25526-93-6
alovudine

Conditions

Conditions	Yield
With Dowex 50 In ethanol; water	93%

: 585540-19-8
1-(2-chloro-2,3-dideoxy-3-fluoro-β-D-ribofuranosyl)thymine

: 25526-93-6
alovudine

Conditions

Conditions	Yield
With azobisisobutyronitrile; tri-n-butyl-tin hydride In 1,4-dioxane for 2h; Heating;	90%

: 152711-06-3
Benzoic acid (2R,3S,5R)-3-fluoro-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester

: 25526-93-6
alovudine

Conditions

Conditions	Yield
With ammonia In methanol for 18h; Ambient temperature;	85%

: 51247-07-5
5'-O-Acetyl-3'-desoxy-3'-fluor-thymidin

: 25526-93-6
alovudine

Conditions

Conditions	Yield
With sodium methylate In methanol	85%

NaOMe powder: NaOMe powder

: 51247-07-5
5'-O-Acetyl-3'-desoxy-3'-fluor-thymidin

: 25526-93-6
alovudine

Conditions

Conditions	Yield
In methanol	85%

: 25442-42-6
5'-O-trityl-2,3'-anhydrothymidine

A: 135197-63-6
3'-Fluoro-5'-O-trityl-deoxythymidine

B: 25526-93-6
alovudine

Conditions

Conditions	Yield
With hydrogen fluoride; diethylaluminum fluoride In 1,2-dimethoxyethane; n-heptane at 65℃; for 4h;	A 65% B 44%

: 135197-63-6
3'-Fluoro-5'-O-trityl-deoxythymidine

: 25526-93-6
alovudine

Conditions

Conditions	Yield
With toluene-4-sulfonic acid In methanol; chloroform at 40℃; for 0.333333h;	64%
With acetic acid at 90℃;
With acetic acid at 25℃; for 3h;	1.28 g

: 585540-13-2
Benzoic acid (2R,3R,4S)-4-chloro-3-fluoro-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester

A: 116209-63-3
1-(2,3-dideoxy-3-fluoro-α-D-erythro-pentofuranosyl)-thymine

B: 25526-93-6
alovudine

Conditions

Conditions	Yield
Stage #1: Benzoic acid (2R,3R,4S)-4-chloro-3-fluoro-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester With azobisisobutyronitrile; tri-n-butyl-tin hydride In 1,4-dioxane for 2h; Heating; Stage #2: With ammonia In methanol at 20℃; for 24h;	A 27% B 55%

: 129468-52-6, 129468-53-7
1-<2,3-Dideoxy-3-fluoro-5-O-(4-phenylbenzoyl)-α/β-D-erythro-pentofuranosy>-5-methyl-2,4(1H,3H)-pyrimidinedione

: 25526-93-6
alovudine

Conditions

Conditions	Yield
With ammonia In methanol for 24h; Ambient temperature;	50%

: [(2R,3S)-3-Fluoro-5-(5-methyl-2,4-bis-trimethylsilanyloxy-2H-pyrimidin-1-yl)-tetrahydro-furan-2-yl]-methanol

A: 116209-63-3
1-(2,3-dideoxy-3-fluoro-α-D-erythro-pentofuranosyl)-thymine

B: 25526-93-6
alovudine

Conditions

Conditions	Yield
With tetrabutyl ammonium fluoride In tetrahydrofuran for 0.5h; Ambient temperature;	A 20% B 44%

: 15981-86-9
1-(2,3'-Anhydro-5'-O-methylsulfonyl-2-deoxy-β-D-threo-pentofuranosyl)thymine

A: 51247-06-4
3'-deoxy-3'-fluoro-5'-O-mesylthymidine

B: 25526-93-6
alovudine

Conditions

Conditions	Yield
With triethylamine tris(hydrogen fluoride) at 150℃; for 1.5h;	A 19% B 5%

: 15981-92-7
2,3'-anhydrothymidine

: 25526-93-6
alovudine

Conditions

Conditions	Yield
With hydrogen fluoride; diisobutylaluminium hydride In tetrahydrofuran; 1,2-dimethoxyethane at 65℃; for 4h;	17%

: (+)-trans-(5R,6R)-5-bromo-6-methoxy-5,6-dihydro-3'-fluoro-3'-deoxythymidine

: 25526-93-6
alovudine

Conditions

Conditions	Yield
With GLUTATHIONE In various solvent(s) at 37℃; for 0.5h; Mechanism; other 5-halo-6-methoxy(or azido)-5,6-dihydro-3'-fluoro-3'-deoxythymidines;	10%

: 134614-83-8, 134614-84-9
2,2-Dimethyl-propionic acid (2R,3S)-3-fluoro-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester

A: 116209-63-3
1-(2,3-dideoxy-3-fluoro-α-D-erythro-pentofuranosyl)-thymine

B: 25526-93-6
alovudine

Conditions

Conditions	Yield
With potassium hydroxide In ethanol Yield given. Yields of byproduct given;

: 15981-86-9
1-(2,3'-Anhydro-5'-O-methylsulfonyl-2-deoxy-β-D-threo-pentofuranosyl)thymine

: 25526-93-6
alovudine

Conditions

Conditions	Yield
With aluminum(III) fluoride; sodium hydroxide; hydrogen fluoride 1) DMF, 75 min, 100 deg C, 2) EtOH, 20 min, reflux; Yield given. Multistep reaction;
Multi-step reaction with 2 steps 1: 19 percent / trishydrogenefluoride triethylamine / 1.5 h / 150 °C 2: 0.1 N NaOCH3 / methanol View Scheme
Multi-step reaction with 2 steps 1: 29.5 percent / dimethylformamide / 1.25 h / 110 °C 2: 0.1 N NaOCH3 / methanol View Scheme

: 42214-24-4
1-(2-deoxy-3-O-methanesulfonyl-5-O-trityl-β-D-ribopentofuranosyl)thymine

A: 3056-17-5
stavudin

B: 25526-93-6
alovudine

Conditions

Conditions	Yield
With tetrabutyl ammonium fluoride; acetic acid 1.) THF, RT, 32 h, 2.) 110 deg C, 15 min; Yield given. Multistep reaction. Yields of byproduct given;
With diethylamino-sulfur trifluoride; acetic acid 1.) THF, benzene, 2 h, 2.) 100 deg C, 15 min; Yield given. Multistep reaction. Yields of byproduct given;

: 51247-06-4
3'-deoxy-3'-fluoro-5'-O-mesylthymidine

: 25526-93-6
alovudine

Conditions

Conditions	Yield
With sodium methylate In methanol Yield given;

: 1-[(2R,4S,5R)-4-Fluoro-5-(2-methyl-4-oxo-4H-benzo[1,3]dioxin-2-yloxymethyl)-tetrahydro-furan-2-yl]-5-methyl-1H-pyrimidine-2,4-dione

A: 25526-93-6
alovudine

B: 51247-07-5
5'-O-Acetyl-3'-desoxy-3'-fluor-thymidin

Conditions

Conditions	Yield
With growth medium RPMI 1640 at 37℃; for 19h; Product distribution;

: 3-{5-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-fluoro-tetrahydro-furan-2-yl}-5-methyl-2,6-dioxo-3,6-dihydro-2H-pyrimidine-1-carboxylic acid tert-butyl ester

: 25526-93-6
alovudine

: 50-89-5
thymidine

: 25526-93-6
alovudine

Conditions

Conditions	Yield
Multistep reaction.;	39 mg

: 3-N-tert-butoxycarbonyl-(5'-O-(4,4'-dimethoxytriphenylmethyl)-2'-deoxy-3'-O-(4-nitrobenzenesulfonyl)-β-D-threo-pentofuranosyl)thymine

: 25526-93-6
alovudine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: potassium fluoride; Kryptofix / acetonitrile View Scheme

: 139212-95-6
5'-O-tert-butyldiphenylsilyl-3'-O-methanesulfonylthymidine

: 25526-93-6
alovudine

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: 70 percent / aq. sodium hydroxide / ethanol / 4 h / Heating 2: N,N-dimethylaminopyridine / dimethylformamide / 4 h / 50 °C 3: diethylaminosulfurtrifluoride / CH2Cl2 / 0 - 25 °C 4: 1.28 g / aq. AcOH / 3 h / 25 °C View Scheme

: 101527-40-6
5'-O-tert-butyldiphenylsilylthymidine

: 25526-93-6
alovudine

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: 9.65 g / 0 - 25 °C 2: 70 percent / aq. sodium hydroxide / ethanol / 4 h / Heating 3: N,N-dimethylaminopyridine / dimethylformamide / 4 h / 50 °C 4: diethylaminosulfurtrifluoride / CH2Cl2 / 0 - 25 °C 5: 1.28 g / aq. AcOH / 3 h / 25 °C View Scheme

: 16053-52-4
threothymidine

: 25526-93-6
alovudine

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: N,N-dimethylaminopyridine / dimethylformamide / 4 h / 50 °C 2: diethylaminosulfurtrifluoride / CH2Cl2 / 0 - 25 °C 3: 1.28 g / aq. AcOH / 3 h / 25 °C View Scheme

: 50-89-5
thymidine

o-xylyl halide: o-xylyl halide

: 25526-93-6
alovudine

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1: pyridine / 25 °C 2: 9.65 g / 0 - 25 °C 3: 70 percent / aq. sodium hydroxide / ethanol / 4 h / Heating 4: N,N-dimethylaminopyridine / dimethylformamide / 4 h / 50 °C 5: diethylaminosulfurtrifluoride / CH2Cl2 / 0 - 25 °C 6: 1.28 g / aq. AcOH / 3 h / 25 °C View Scheme

: 55612-11-8
5'-O-trityldeoxyxylothymidine

: 25526-93-6
alovudine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: diethylaminosulfurtrifluoride / CH2Cl2 / 0 - 25 °C 2: 1.28 g / aq. AcOH / 3 h / 25 °C View Scheme
Multi-step reaction with 2 steps 1: DAST; pyridine / CH2Cl2 2: aq. AcOH / 90 °C View Scheme
Multi-step reaction with 3 steps 1: 86 percent / pyridine / 1.) 22 h, 2.) rt, 3 h 2: 57 percent / KF, 18-crown-6 ether / dimethylformamide / 1 h / 100 °C 3: 64 percent / p-toluenesulfonic acid / CHCl3; methanol / 0.33 h / 40 °C View Scheme
Multi-step reaction with 2 steps 1: diethylamino sulfur trifluoride (DAST) / CH2Cl2 / 1 h / Ambient temperature 2: 64 percent / p-toluenesulfonic acid / CHCl3; methanol / 0.33 h / 40 °C View Scheme

: 133776-09-7
methyl 3-deoxy-5-O-benzoyl-3-fluoro-2-O-tosyl-β-D-arabinofuranoside

: 25526-93-6
alovudine

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: 72 percent / LiCl / dimethylsulfoxide / 2 h / Heating 2.1: trimethylsilyl triflate 2.2: 49 percent / acetonitrile / 5 h / Heating 3.1: tributyltin hydride; α,α'-azobisisobutyronitrile / dioxane / 2 h / Heating 3.2: 55 percent / NH3 / methanol / 24 h / 20 °C View Scheme
Multi-step reaction with 4 steps 1.1: 72 percent / LiCl / dimethylsulfoxide / 2 h / Heating 2.1: trimethylsilyl triflate 2.2: 49 percent / acetonitrile / 5 h / Heating 3.1: 55 percent / NH3 / methanol / 24 h / 20 °C 4.1: 90 percent / tributyltin hydride; α,α'-azobisisobutyronitrile / dioxane / 2 h / Heating View Scheme

: 126716-24-3
methyl 5-O-benzyl-2-O-tosyl-3-fluoro-3-deoxy-β-D-arabino-furanoside

: 25526-93-6
alovudine

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1.1: 55 percent / LiCl / dimethylsulfoxide / 2 h / Heating 2.1: H2 / Pd/C / ethanol / 18 h / 20 °C 3.1: 0.42 g / pyridine / 18 h / 20 °C 4.1: trimethylsilyl triflate 4.2: 49 percent / acetonitrile / 5 h / Heating 5.1: tributyltin hydride; α,α'-azobisisobutyronitrile / dioxane / 2 h / Heating 5.2: 55 percent / NH3 / methanol / 24 h / 20 °C View Scheme
Multi-step reaction with 6 steps 1.1: 55 percent / LiCl / dimethylsulfoxide / 2 h / Heating 2.1: H2 / Pd/C / ethanol / 18 h / 20 °C 3.1: 0.42 g / pyridine / 18 h / 20 °C 4.1: trimethylsilyl triflate 4.2: 49 percent / acetonitrile / 5 h / Heating 5.1: 55 percent / NH3 / methanol / 24 h / 20 °C 6.1: 90 percent / tributyltin hydride; α,α'-azobisisobutyronitrile / dioxane / 2 h / Heating View Scheme
Multi-step reaction with 4 steps 1.1: H2 / Pd/C / ethanol / 18 h / 20 °C 1.2: 71 percent / pyridine / 18 h / 20 °C 2.1: 72 percent / LiCl / dimethylsulfoxide / 2 h / Heating 3.1: trimethylsilyl triflate 3.2: 49 percent / acetonitrile / 5 h / Heating 4.1: tributyltin hydride; α,α'-azobisisobutyronitrile / dioxane / 2 h / Heating 4.2: 55 percent / NH3 / methanol / 24 h / 20 °C View Scheme
Multi-step reaction with 5 steps 1.1: H2 / Pd/C / ethanol / 18 h / 20 °C 1.2: 71 percent / pyridine / 18 h / 20 °C 2.1: 72 percent / LiCl / dimethylsulfoxide / 2 h / Heating 3.1: trimethylsilyl triflate 3.2: 49 percent / acetonitrile / 5 h / Heating 4.1: 55 percent / NH3 / methanol / 24 h / 20 °C 5.1: 90 percent / tributyltin hydride; α,α'-azobisisobutyronitrile / dioxane / 2 h / Heating View Scheme

: C19H26BN2O4(1+)*CF3O3S(1-)

: 25526-93-6
alovudine

: C25H32BFN2O8

Conditions

Conditions	Yield
With dmap In tetrahydrofuran for 16h; Inert atmosphere; Reflux;	99%

: 124482-92-4
2-cyanoethyl-N,N-(diisopropylamino)chlorophosphine

: 25526-93-6
alovudine

: 161006-80-0
3'-fluoro-3'-deoxythymidine-5'-(2-cyanoethyl diisopropylamino) phosphoramidite

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In dichloromethane for 1h; Ambient temperature;	96%

: 25526-93-6
alovudine

: 3'-fluoro-3'-deoxythymidine 5'-fluorophosphoridate

Conditions

Conditions	Yield
With pyridine; bis(tri-n-butylammonium) phosphorofluoridate; 1-(mesitylene-2-sulfonyl)-3-nitro-1H-1,2,4-triazole In N,N-dimethyl-formamide at 20℃; for 0.25h;	91%
With 2,4,6-triisopropylphenylsulfonyl chloride; fluorophosphoric acid tri-n-butylammonium salt In pyridine; N,N-dimethyl-formamide for 0.333333h; Ambient temperature;	62%

: 1365246-87-2
N-myristoyl-Glu(OtBu)-OH

: 25526-93-6
alovudine

: 1365246-88-3
N-myristoyl-Glu(OtBu)-OFLT

Conditions

Conditions	Yield
With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 6h;	91%
With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 6h;	91%

: 58479-61-1
tert-butylchlorodiphenylsilane

: 25526-93-6
alovudine

: 116195-70-1
3'-fluoro-5'-O-tert-butyldiphenylsilyl-3'-deoxythymidine

Conditions

Conditions	Yield
With pyridine at 25℃;	90%

: 2,5-dioxopyrrolidin-1-yl 7-(trifluoromethyl)quinoline-3-carboxylate

: 25526-93-6
alovudine

: ((2R,3S,5R)-3-fluoro-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-2-yl)methyl 7-(trifluoromethyl)-quinoline-3-carboxylate

Conditions

Conditions	Yield
With triethylamine In acetonitrile at 20℃; Inert atmosphere;	87%

: 25526-93-6
alovudine

: 1314761-18-6
3'-fluoro-3'-deoxythymidine-5'-O-β-triphosphate

Conditions

Conditions	Yield
Stage #1: alovudine With C15H26N4O6P3Pol; 5-(ethylthio)-1H-tetrazole In tetrahydrofuran; dimethyl sulfoxide Stage #2: With tert.-butylhydroperoxide In tetrahydrofuran Further stages;	85%

: 2,5-dioxopyrrolidin-1-yl 7-methoxyquinoline-3-carboxylate

: 25526-93-6
alovudine

: ((2R,3S,5R)-3-fluoro-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-2-yl)methyl 7-methoxyquinoline-3-carboxylate

Conditions

Conditions	Yield
With triethylamine In acetonitrile at 80℃; for 72h; Inert atmosphere;	82%

: 25526-93-6
alovudine

: 25520-83-6
phosphoric acid mono[3-fluoro-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)tetrahyrofuran-2-ylmethyl] ester

Conditions

Conditions	Yield
With tris(p-nitrophenyl)phosphate at 50℃; Erwina herbicola 47/3 cells;	81%
With trimethyl phosphite; trichlorophosphate

: 543-20-4
succinoyl dichloride

: 25526-93-6
alovudine

: di[5′-O-(3'-fluoro-2′,3′-dideoxythymidinyl)] 1,4-succinate

Conditions

Conditions	Yield
With dmap In benzene at 20℃;	80%

: 1571-13-7
3,4,5,6-tetrachlorophthalimide

: 25526-93-6
alovudine

: 5'-(4,5,6,7-tetrachloroisoindole-1,3-dione-2-yl)-5',3'-dideoxy-3'-fluorothymidine

Conditions

Conditions	Yield
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 20℃; for 96h; Inert atmosphere;	80%

: Tributyl-amine; compound with difluoromethyl-phosphonic acid

: 25526-93-6
alovudine

: Difluoromethyl-phosphonic acid mono-[(2R,3S,5R)-3-fluoro-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl] ester

Conditions

Conditions	Yield
With pyridine; 2,4,6-triisopropylphenylsulfonyl chloride In N,N-dimethyl-formamide for 0.5h; Ambient temperature;	78%

: 127369-50-0
2,5-dioxopyrrolidin-1-yl quinoline-3-carboxylate

: 25526-93-6
alovudine

: ((2R,3S,5R)-3-fluoro-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-2-yl)methyl quinoline-3-carboxylate

Conditions

Conditions	Yield
With triethylamine In acetonitrile at 80℃; for 24h; Inert atmosphere;	77%

: Tributyl-amine; compound with fluoromethyl-phosphonic acid

: 25526-93-6
alovudine

: Fluoromethyl-phosphonic acid mono-[(2R,3S,5R)-3-fluoro-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl] ester

Conditions

Conditions	Yield
With pyridine; 2,4,6-triisopropylphenylsulfonyl chloride In N,N-dimethyl-formamide for 0.5h; Ambient temperature;	76%

: Tributyl-amine; compound with iodomethyl-phosphonic acid

: 25526-93-6
alovudine

: Iodomethyl-phosphonic acid mono-[(2R,3S,5R)-3-fluoro-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl] ester

Conditions

Conditions	Yield
With pyridine; 2,4,6-triisopropylphenylsulfonyl chloride In N,N-dimethyl-formamide for 0.5h; Ambient temperature;	76%

: 25526-93-6
alovudine

: 1983-26-2
chloromethylphosphonic dichloride

: 3'-fluoro-3'-deoxythymidine-5'-chloromethylphosphonate

Conditions

Conditions	Yield
With triethyl phosphate at 0℃;	76%

: 1262015-14-4
4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl 1H-imidazole-1-carboxylate

: 25526-93-6
alovudine

: C24H30BFN2O8

Conditions

Conditions	Yield
With dmap In tetrahydrofuran for 3.5h; Inert atmosphere; Reflux;	75%

: 821-38-5
1,14-tetradecanedioic acid

: 25526-93-6
alovudine

: 3'-fluoro-2′,3′-dideoxy-5'-O-(13-carboxyltridecanoate)thymidine

Conditions

Conditions	Yield
With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 4h;	75%

: Tributyl-amine; compound with vinyl-phosphonic acid

: 25526-93-6
alovudine

: Vinyl-phosphonic acid mono-[(2R,3S,5R)-3-fluoro-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl] ester

Conditions

Conditions	Yield
With pyridine; 2,4,6-triisopropylphenylsulfonyl chloride In N,N-dimethyl-formamide for 0.5h; Ambient temperature;	72%

: C12H27N*C3H7O5P

: 25526-93-6
alovudine

: C13H18FN2O8P

Conditions

Conditions	Yield
With pyridine; 2,4,6-triisopropylphenylsulfonyl chloride In N,N-dimethyl-formamide for 0.333333h; Ambient temperature;	70%

: 108-30-5
succinic acid anhydride

: 25526-93-6
alovudine

: 1099829-97-6
5'-O-(succinate)-3'-fluoro-2',3'-dideoxythymidine

Conditions

Conditions	Yield
With pyridine at 20℃;	70%
With pyridine

: Tributyl-amine; compound with acetic acid phosphonomethyl ester

: 25526-93-6
alovudine

: Acetic acid [(2R,3S,5R)-3-fluoro-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethoxy]-hydroxy-phosphorylmethyl ester

Conditions

Conditions	Yield
With pyridine; 2,4,6-triisopropylphenylsulfonyl chloride In N,N-dimethyl-formamide for 0.333333h; Ambient temperature;	69%

: 762-49-2
2-fluoroethyl bromide

: 25526-93-6
alovudine

: 887113-64-6
C12H16F2N2O4

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 20℃;	69%

3'-Deoxy-3'-fluorothymidine Specification

The 3'-Deoxy-3'-fluorothymidine, with the CAS registry number 25526-93-6, has the IUPAC name of 1-[(2R,4S,
5R)-4-fluoro-5-(hydroxymethyl)oxolan-2-yl]-5-methylpyrimidine-2,4-dione. And the molecular formula of this chemical is C₁₀H₁₃FN₂O₄. It is a kind of colorless solid, and belongs to the following product categories: API; Bases & Related Reagents; Carbohydrates & Derivatives; Nucleotides; Nucleosides; Oligonucleotide Synthesis; Specialty Synthesis. What's more, it is used as an antiviral agent.

The physical properties of 3'-Deoxy-3'-fluorothymidine are as following: (1)ACD/LogP: -0.52; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -0.52; (4)ACD/LogD (pH 7.4): -0.53; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 12.39; (8)ACD/KOC (pH 7.4): 12.21; (9)#H bond acceptors: 6; (10)#H bond donors: 2; (11)#Freely Rotating Bonds: 3; (12)Polar Surface Area: 59.08 Å²; (13)Index of Refraction: 1.565; (14)Molar Refractivity: 55.03 cm³; (15)Molar Volume: 168.8 cm³; (16)Polarizability: 21.81×10^-24cm³; (17)Surface Tension: 55.3 dyne/cm; (18)Density: 1.44 g/cm³.

You can still convert the following datas into molecular structure:
(1)SMILES: O=C/1NC(=O)N(\C=C\1C)[C@@H]2O[C@@H]([C@@H](F)C2)CO
(2)InChI: InChI=1/C10H13FN2O4/c1-5-3-13(10(16)12-9(5)15)8-2-6(11)7(4-14)17-8/h3,6-8,14H,2,4H2,1H3,(H,12,15,16)/t6-,7+,8+/m0/s1
(3)InChIKey: UXCAQJAQSWSNPQ-XLPZGREQBJ

Product Name

3'-Deoxy-3'-fluorothymidine

Synthetic route

3'-Deoxy-3'-fluorothymidine Specification

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