Floxuridine supplier | CasNO.50-91-9

Name
Floxuridine
EINECS 200-072-5
CAS No. 50-91-9
Article Data50
CAS DataBase
Density 1.64 g/cm³
Solubility soluble in water
Melting Point 148 °C(lit.)
Formula C₉H₁₁FN₂O₅
Boiling Point 150 °C
Molecular Weight 246.195
Flash Point
Transport Information UN 2811 6.1/PG 3
Appearance white solid
Safety 22-36/37/39-26
Risk Codes 68-36/37/38-40-20/21/22
Molecular Structure
Hazard Symbols Xn,T,Xi
Synonyms 1-(2-Deoxy-b-D-ribofuranosyl)-5-fluorouracil;5-Fluoro-2'-deoxy-b-uridine;5-Fluoro-2'-deoxyuridine;5-Fluorodeoxyuridine;5-Fluorouracil 2'-deoxyriboside;5-Fluorouracil deoxyriboside;Floxuridin;NSC 26740;NSC 27640;2'-Deoxy-5-fluorouridine;
PSA 104.55000
LogP -1.68360

Synthetic route

: 1384553-43-8
5-fluoro-1-(3',5'-di-O-p-methoxybenzoyl-2'-deoxy-D-ribofuranosyl)uracil

: 50-91-9
5-Fluoro-2'-deoxyuridine

Conditions

Conditions	Yield
With sodium methylate In methanol at 20℃; for 3h;	98%

: 1582-79-2
3',5'-di-O-(p-chlorobenzoyl)-5-fluoro-2'-deoxy-β-uridine

: 50-91-9
5-Fluoro-2'-deoxyuridine

Conditions

Conditions	Yield
With methanol; ammonia at 10 - 25℃;	86.2%
With ammonia In methanol at 30℃; for 16h;
With methanol; barium methoxide

: 51-21-8
5-fluorouracil

: 7-methyl-2′-deoxyguanosine hydroiodide

: 50-91-9
5-Fluoro-2'-deoxyuridine

Conditions

Conditions	Yield
With potassium dihydrogenphosphate; Escherichia coli thymidine phosphorylase; Escherichia coli purine nucleoside phosphorylase In aq. buffer at 20℃; for 20h; pH=7.5; Enzymatic reaction;	81%

: 51-21-8
5-fluorouracil

: 951-78-0
2'-deoxyuridine

: 50-91-9
5-Fluoro-2'-deoxyuridine

Conditions

Conditions	Yield
at 37℃; for 16h; alginate gel-entrapped cells of auxotrophic thymine-dependent strain of E. coli, ammonium acetate buffer pH 5.8;	62%
With purine nucleoside phosphorylase; uridine phosphorylase In aq. phosphate buffer; dimethyl sulfoxide at 80℃; for 3h; Enzymatic reaction;

: 51-21-8
5-fluorouracil

: 50-89-5
thymidine

: 50-91-9
5-Fluoro-2'-deoxyuridine

Conditions

Conditions	Yield
With Lactobacillus animalis ATCC 35046 2’-N-deoxyribosyltransferase immobilized in DEAE-Sepharose In aq. buffer at 30℃; pH=7; Concentration; Reagent/catalyst; Green chemistry; Enzymatic reaction;	35%
With thymidine phosphorylase In aq. phosphate buffer at 37℃; for 0.2h; pH=6.8; Enzymatic reaction;
With ammonium dihydrogen phosphate; ammonia In water at 45 - 55℃; for 45h; pH=6.6; Large scale; Enzymatic reaction;
With recobinant purine nucleoside phosphorylase from Escherichia coli In aq. phosphate buffer pH=6.8; Heating; Enzymatic reaction;

: 51-21-8
5-fluorouracil

: 1463-10-1
5-Methyluridine

: 50-91-9
5-Fluoro-2'-deoxyuridine

Conditions

Conditions	Yield
With lactobacillus animalis ATCC 35046 at 30℃; for 0.5h; pH=7; aq. buffer; Enzymatic reaction;	22%

: 7585-89-9
5-fluoro-O3',O5'-bis-(4-methyl-benzoyl)-2'-deoxy-uridine

: 50-91-9
5-Fluoro-2'-deoxyuridine

Conditions

Conditions	Yield
With methanol; barium methoxide
With methanol; barium methoxide

: 951-78-0
2'-deoxyuridine

: 78948-09-1
acetyl hypofluorite

A: 3180-64-1, 13964-07-3, 119180-46-0, 119180-47-1
(5S,6R)-5-Fluoro-6-hydroxy-1-((2R,4S,5R)-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-dihydro-pyrimidine-2,4-dione

B: 3180-64-1, 13964-07-3, 119180-46-0, 119180-47-1
(5R,6S)-5-Fluoro-6-hydroxy-1-((2R,4S,5R)-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-dihydro-pyrimidine-2,4-dione

C: 119003-28-0, 119068-00-7
Acetic acid (4R,5S)-5-fluoro-3-((2R,4S,5R)-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-2,6-dioxo-hexahydro-pyrimidin-4-yl ester

D: 119003-28-0, 119068-00-7
Acetic acid (4S,5R)-5-fluoro-3-((2R,4S,5R)-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-2,6-dioxo-hexahydro-pyrimidin-4-yl ester

E: 50-91-9
5-Fluoro-2'-deoxyuridine

Conditions

Conditions	Yield
In acetic acid Product distribution; different solvents (AcOH,H2O), various nucleosides;	A n/a B n/a C n/a D n/a E 5 % Chromat.

...Expand

: 951-78-0
2'-deoxyuridine

: 78948-09-1
acetyl hypofluorite

A: 3180-64-1, 13964-07-3, 119180-46-0, 119180-47-1
(5R,6S)-5-Fluoro-6-hydroxy-1-((2R,4S,5R)-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-dihydro-pyrimidine-2,4-dione

B: 119003-28-0, 119068-00-7
Acetic acid (4R,5S)-5-fluoro-3-((2R,4S,5R)-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-2,6-dioxo-hexahydro-pyrimidin-4-yl ester

C: 119003-28-0, 119068-00-7
Acetic acid (4S,5R)-5-fluoro-3-((2R,4S,5R)-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-2,6-dioxo-hexahydro-pyrimidin-4-yl ester

D: 50-91-9
5-Fluoro-2'-deoxyuridine

Conditions

Conditions	Yield
In acetic acid Yield given. Further byproducts given. Yields of byproduct given;

...Expand

: 951-78-0
2'-deoxyuridine

A: 3180-64-1, 13964-07-3, 119180-46-0, 119180-47-1
(5S,6R)-5-Fluoro-6-hydroxy-1-((2R,4S,5R)-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-dihydro-pyrimidine-2,4-dione

B: 119003-28-0, 119068-00-7
Acetic acid (4R,5S)-5-fluoro-3-((2R,4S,5R)-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-2,6-dioxo-hexahydro-pyrimidin-4-yl ester

C: 119003-28-0, 119068-00-7
Acetic acid (4S,5R)-5-fluoro-3-((2R,4S,5R)-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-2,6-dioxo-hexahydro-pyrimidin-4-yl ester

D: 50-91-9
5-Fluoro-2'-deoxyuridine

Conditions

Conditions	Yield
With acetyl hypofluorite In water Yield given. Further byproducts given;	A n/a B n/a C n/a D 5 % Chromat.

...Expand

: 951-78-0
2'-deoxyuridine

A: 3180-64-1, 13964-07-3, 119180-46-0, 119180-47-1
(5R,6S)-5-Fluoro-6-hydroxy-1-((2R,4S,5R)-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-dihydro-pyrimidine-2,4-dione

B: 119003-28-0, 119068-00-7
Acetic acid (4R,5S)-5-fluoro-3-((2R,4S,5R)-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-2,6-dioxo-hexahydro-pyrimidin-4-yl ester

C: 119003-28-0, 119068-00-7
Acetic acid (4S,5R)-5-fluoro-3-((2R,4S,5R)-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-2,6-dioxo-hexahydro-pyrimidin-4-yl ester

D: 50-91-9
5-Fluoro-2'-deoxyuridine

Conditions

Conditions	Yield
With acetyl hypofluorite In acetic acid Further byproducts given. Yields of byproduct given;	A n/a B n/a C n/a D 5 % Chromat.
With acetyl hypofluorite In water Yield given. Further byproducts given. Yields of byproduct given;

...Expand

: 3415-69-8
3',5'-O-dicaproyl-floxuridine

A: 123739-84-4
3'-O-caproyl-floxuridine

B: 50-91-9
5-Fluoro-2'-deoxyuridine

Conditions

Conditions	Yield
With phosphate buffer In N,N-dimethyl-formamide at 25℃; for 18h; enzym: Subtilisin;	A 22 % Chromat. B 71 % Chromat.

: 3415-69-8
3',5'-O-dicaproyl-floxuridine

A: 123739-84-4
3'-O-caproyl-floxuridine

B: 123739-81-1
5'-O-caproyl-floxuridine

C: 50-91-9
5-Fluoro-2'-deoxyuridine

Conditions

Conditions	Yield
porcine liver esterase In water at 37℃; Rate constant; pH=7.00; enzyme concentration dependence;

...Expand

: 3415-69-8
3',5'-O-dicaproyl-floxuridine

A: 123739-81-1
5'-O-caproyl-floxuridine

B: 50-91-9
5-Fluoro-2'-deoxyuridine

Conditions

Conditions	Yield
With phosphate buffer In N,N-dimethyl-formamide at 25℃; for 18h; enzym: Pseudomonas fluorescens;	A 74 % Chromat. B 26 % Chromat.

: 3343-22-4
3',5'-di-O-butanoyl-5-fluoro-2'-deoxyuridine

A: 7207-60-5
3'-O-butanoyl-5-fluoro-2'-deoxyuridine

B: 7207-61-6
5'-O-butanoyl-5-fluoro-2'-deoxyuridine

C: 50-91-9
5-Fluoro-2'-deoxyuridine

Conditions

Conditions	Yield
porcine liver esterase In water at 37℃; Rate constant; pH=7.00; enzyme concentration dependence;

...Expand

: 3415-70-1
3',5'-O-dioctanoyl-floxuridine

A: 86977-19-7
3'-O-octanoyl-floxuridine

B: 118694-10-3
5'-O-octanoyl-floxuridine

C: 50-91-9
5-Fluoro-2'-deoxyuridine

Conditions

Conditions	Yield
porcine liver esterase In water at 37℃; Rate constant; pH=7.00; enzyme concentration dependence;

...Expand

: 7207-65-0
3',5'-O-didecanoyl-floxuridine

A: 118694-11-4
3'-O-decanoyl-floxuridine

B: 118694-12-5
5'-O-decanoyl-floxuridine

C: 50-91-9
5-Fluoro-2'-deoxyuridine

Conditions

Conditions	Yield
porcine liver esterase In water at 37℃; Rate constant; pH=7.00; enzyme concentration dependence;

...Expand

: 7207-66-1
3',5'-O-dilauroyl-floxuridine

A: 118694-13-6
3'-O-lauroyl-floxuridine

B: 118694-14-7
5'-O-lauroyl-floxuridine

C: 50-91-9
5-Fluoro-2'-deoxyuridine

Conditions

Conditions	Yield
porcine liver esterase In water at 37℃; Rate constant; pH=7.00; enzime concentration dependence;

...Expand

: 119003-28-0, 119068-00-7
Acetic acid (4R,5S)-5-fluoro-3-((2R,4S,5R)-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-2,6-dioxo-hexahydro-pyrimidin-4-yl ester

: 50-91-9
5-Fluoro-2'-deoxyuridine

Conditions

Conditions	Yield
In triethylamine at 70℃; for 0.5h;

: 119003-28-0, 119068-00-7
Acetic acid (4S,5R)-5-fluoro-3-((2R,4S,5R)-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-2,6-dioxo-hexahydro-pyrimidin-4-yl ester

: 50-91-9
5-Fluoro-2'-deoxyuridine

Conditions

Conditions	Yield
In triethylamine at 70℃; for 0.5h;

: 110238-43-2
2'-deoxy-5-fluoro-5'-O-(1,3-dithian-2-yl)uridine

: 50-91-9
5-Fluoro-2'-deoxyuridine

Conditions

Conditions	Yield
In methanol; water Product distribution; Mechanism; Ambient temperature; Irradiation; other 5'-O-substituted 2'-deoxy-5-fluorouridine, var. solvents (saturated or no with nitrous oxide);

: 110238-48-7
3-dimethylsulfoxyimidyl-5-fluorouridine

: 50-91-9
5-Fluoro-2'-deoxyuridine

Conditions

Conditions	Yield
In methanol; water at 20℃; Product distribution; Mechanism; Irradiation; other 3-substituted 5-fluorouridine and 2'-deoxy-5-fluorouridine, var. solvents saturated with oxygen or nitrogen;

: 111245-27-3
3'-(7-carboxyheptanoyl)-5-fluoro-2'-deoxyuridine

: 50-91-9
5-Fluoro-2'-deoxyuridine

Conditions

Conditions	Yield
With esterase (porcine liver) at 37.5℃; for 2h; Product distribution; In vitro drug release studies: enzymatic and nonenzymatic processes; var. reaction cond.;

: 5'-(Cortisol-21-phosphoryl)-5-fluoro-2'-deoxyuridine ammonium salt

A: 3863-59-0
hydrocortisone 21-phosphate

B: 50-91-9
5-Fluoro-2'-deoxyuridine

Conditions

Conditions	Yield
With barium dihydroxide at 90 - 95℃; for 0.25h; Product distribution;

: 4564-21-0
5-fluoro-O3',O5'-dipropionyl-2'-deoxy-uridine

A: Propionic acid (2R,3S,5R)-5-(5-fluoro-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2-hydroxymethyl-tetrahydro-furan-3-yl ester

B: Propionic acid (2R,3S,5R)-5-(5-fluoro-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-3-hydroxy-tetrahydro-furan-2-ylmethyl ester

C: 50-91-9
5-Fluoro-2'-deoxyuridine

Conditions

Conditions	Yield
porcine liver esterase In water at 37℃; Rate constant; pH=7.00; enzyme concentration dependence;

...Expand

: 110522-47-9, 7207-56-9
1-(2'-deoxy-3',5'-tri-O-acetyl-β-D-ribofuranosyl)-5-fluorouracil

A: 2823-52-1
5'-O-acetyl-floxuridine

B: 2059-38-3
3′-O-acetyl-5-fluoro-2′-deoxyuridine

C: 50-91-9
5-Fluoro-2'-deoxyuridine

Conditions

Conditions	Yield
porcine liver esterase In water at 37℃; Rate constant; pH=7.00; enzyme concentration dependence;

...Expand

: 2691-71-6
3',5'-di-O-benzoyl-5-fluoro-2'-deoxyuridine

: 50-91-9
5-Fluoro-2'-deoxyuridine

Conditions

Conditions	Yield
With sodium methylate In methanol Ambient temperature;
With sodium hydroxide In methanol at 20 - 30℃; Large scale;

: Carbonic acid 4,5-dimethoxy-2-nitro-benzyl ester (2R,3S,5R)-5-(5-fluoro-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-3-hydroxy-tetrahydro-furan-2-ylmethyl ester

A: 124-38-9
carbon dioxide

B: 119137-07-4
4,5-dimethoxy-2-nitrosobenzaldehyde

C: 50-91-9
5-Fluoro-2'-deoxyuridine

Conditions

Conditions	Yield
With sodium phosphate buffer at 4℃; Product distribution; Irradiation; var. times;

...Expand

: 287731-60-6
2-((S)-2-Formylamino-4-methylsulfanyl-butyrylamino)-2-methyl-propionic acid (2R,3S,5R)-5-(5-fluoro-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-3-hydroxy-tetrahydro-furan-2-ylmethyl ester

A: (S)-3,3-Dimethyl-6-(2-methylsulfanyl-ethyl)-piperazine-2,5-dione

B: 50-91-9
5-Fluoro-2'-deoxyuridine

Conditions

Conditions	Yield
With phosphate buffer; peptide deformylase from E. coli pH=7.4; Enzyme kinetics; deformylation; intramolecular cyclization;

: 14470-28-1
mono-4-methoxytrityl chloride

: 50-91-9
5-Fluoro-2'-deoxyuridine

: 103767-37-9
5'-O-(4-monomethoxytrityl)-2'-deoxy-5-fluorouridine

Conditions

Conditions	Yield
With pyridine for 48h; Ambient temperature;	100%
With pyridine at 20℃; for 5h;	94%
In pyridine for 24h; Ambient temperature;	86%

: 3896-58-0
vinyl oleate

: 50-91-9
5-Fluoro-2'-deoxyuridine

A: 143767-53-7
5'-O-oleoyl-FUdR

B: 3'-O-oleoyl-FUdR

C: 7207-70-7
3',5'-dioleoyl floxuridine

Conditions

Conditions	Yield
With PSL-C; 1-n-butyl-2,3-dimethylimidazolium hexafluorophosphate In tetrahydrofuran at 40℃; for 9h; regioselective reaction;	A n/a B 99% C n/a

...Expand

: 108-24-7
acetic anhydride

: 50-91-9
5-Fluoro-2'-deoxyuridine

: 110522-47-9, 7207-56-9
1-(2'-deoxy-3',5'-tri-O-acetyl-β-D-ribofuranosyl)-5-fluorouracil

Conditions

Conditions	Yield
With pyridine at 20℃; for 8h;	97%
With dmap In pyridine
With pyridine at 0℃; for 5h;
With dmap; triethylamine In dichloromethane at -10 - 5℃; Large scale;

: 3958-60-9
2-nitrophenylmethyl bromide

: 50-91-9
5-Fluoro-2'-deoxyuridine

: 98653-16-8
3-(o-nitrobenzyl)-2'-deoxy-5-fluorouridine

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide for 2h; Ambient temperature;	97%

: 18162-48-6
tert-butyldimethylsilyl chloride

: 50-91-9
5-Fluoro-2'-deoxyuridine

: 150109-68-5
1-((2R,4S,5R)-4-((tert-butyldimethylsilyl)oxy)-5-(((tert-butyldimethylsilyl)oxy)methyl)tetrahydrofuran-2-yl)-5-fluoropyrimidine-2,4(1H,3H)dione

Conditions

Conditions	Yield
Stage #1: tert-butyldimethylsilyl chloride With 1H-imidazole In dichloromethane at 0℃; Inert atmosphere; Stage #2: 5-Fluoro-2'-deoxyuridine In dichloromethane at 20℃; Inert atmosphere;	97%
Stage #1: 5-Fluoro-2'-deoxyuridine With 1H-imidazole In N,N-dimethyl-formamide at 20℃; for 0.0833333h; Stage #2: tert-butyldimethylsilyl chloride In N,N-dimethyl-formamide at 20℃; for 2h;	91%
With 1H-imidazole; dmap In N,N-dimethyl-formamide at 25℃; for 1h;
Stage #1: 5-Fluoro-2'-deoxyuridine With 1H-imidazole In dichloromethane for 0.5h; Inert atmosphere; Cooling with ice; Stage #2: tert-butyldimethylsilyl chloride In dichloromethane at 20℃; for 1h; Inert atmosphere;

: 3377-92-2
vinyl pivalate

: 50-91-9
5-Fluoro-2'-deoxyuridine

A: 1072440-12-0
3'-O-pivaloyl-FUdR

B: 107036-58-8
1-<2'-deoxy-5'-O-(trimethylacetyl)-β-D-ribofuranosyl>-5-fluorouracil

Conditions

Conditions	Yield
With PSL-C; 1-n-butyl-2,3-dimethylimidazolium hexafluorophosphate In tetrahydrofuran at 50℃; for 66h; Reactivity; Temperature; Time; regioselective reaction;	A 96% B n/a

...Expand

: 76-83-5
trityl chloride

: 124-63-0
methanesulfonyl chloride

: 50-91-9
5-Fluoro-2'-deoxyuridine

: 101039-89-8
1-(2-deoxy-3-O-methanesulfonyl-5-O-trityl-β-D-ribopentofuranosyl)-5-fluorouracil

Conditions

Conditions	Yield
Stage #1: trityl chloride; 5-Fluoro-2'-deoxyuridine With pyridine at 100℃; for 0.5h; Stage #2: methanesulfonyl chloride at 20℃; for 2h;	95%

...Expand

: 40615-36-9
4,4'-dimethoxytrityl chloride

: 50-91-9
5-Fluoro-2'-deoxyuridine

: 104495-48-9
1-((2R,4S,5R)-5-((bis(4-methoxyphenyl)(phenyl)methoxy)methyl)-4-hydroxytetrahydrofuran-2-yl)-5-fluoropyrimidine-2,4(1H,3H)-dione

Conditions

Conditions	Yield
With dmap In pyridine for 4h; Ambient temperature;	94%
With pyridine at 20℃; Inert atmosphere;	92%
With pyridine; triethylamine at 20℃; for 20h;	87%

chloromethyl ester: chloromethyl ester

: 50-91-9
5-Fluoro-2'-deoxyuridine

: 3-n-butoxybutyryloxymethyl-2'-deoxy-5-fluorouridine

Conditions

Conditions	Yield
With sodium iodide; potassium carbonate	92.2%

: 98-59-9
p-toluenesulfonyl chloride

: 50-91-9
5-Fluoro-2'-deoxyuridine

: 10054-41-8
2'-deoxy-5-fluoro-5'-O-<(4-methylphenyl)sulfonyl>uridine

Conditions

Conditions	Yield
With pyridine; triethylamine at 0 - 20℃; for 24h;	90%
With pyridine at 0 - 5℃; for 48h;	65%
With pyridine at 4℃; for 4h;	63%

: 3958-57-4
1-bromomethyl-3-nitrobenzene

: 50-91-9
5-Fluoro-2'-deoxyuridine

: 98653-17-9
3-(m-nitrobenzyl)-2'-deoxy-5-fluorouridine

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide for 2h; Ambient temperature;	90%

: 65-85-0
benzoic acid

: 50-91-9
5-Fluoro-2'-deoxyuridine

: 507232-12-4
2,3'-anhydro-5'-O-benzoyl-5-fluoro-2'-deoxyuridine

Conditions

Conditions	Yield
With di-isopropyl azodicarboxylate; triphenylphosphine In N,N-dimethyl-formamide at 25℃; for 1.5h; Mitsunobu reaction;	90%

: 108-30-5
succinic acid anhydride

: 50-91-9
5-Fluoro-2'-deoxyuridine

: 99194-70-4
3',5'-bis(3-carboxypropionyl)-5-fluoro-2'-deoxyuridine

Conditions

Conditions	Yield
With dmap In pyridine for 12h; Ambient temperature;	88%

: 769-78-8
vinyl benzoate

: 50-91-9
5-Fluoro-2'-deoxyuridine

A: 1006381-74-3
5'-O-benzoyl-FUdR

B: 1995-83-1
(2R,3S,5R)-5-(5-fluoro-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-2-(hydroxymethyl)tetrahydrofuran-3-yl benzoate

C: 2691-71-6
3',5'-di-O-benzoyl-5-fluoro-2'-deoxyuridine

Conditions

Conditions	Yield
With PSL-C; 1-n-butyl-2,3-dimethylimidazolium hexafluorophosphate In tetrahydrofuran at 50℃; for 66h; Reactivity; Time; Temperature; regioselective reaction;	A n/a B 88% C n/a

...Expand

: 91-01-0
1,1-Diphenylmethanol

: 50-91-9
5-Fluoro-2'-deoxyuridine

: 1454883-43-2
3',5'-di-O-benzhydryl-5-fluoro-2'-deoxyuridine

Conditions

Conditions	Yield
With palladium dichloride In 1,2-dichloro-ethane at 85℃; for 16h; Inert atmosphere;	85%
With palladium dichloride In 1,2-dichloro-ethane at 85℃; Inert atmosphere;

: 76-83-5
trityl chloride

: 50-91-9
5-Fluoro-2'-deoxyuridine

: 4031-24-7, 10343-71-2, 103285-11-6
1-(2-deoxy-5-O-trityl-β-D-erythro-pentofuranosyl)-5-fluorouracil

Conditions

Conditions	Yield
With pyridine for 1h; Heating;	84%
With pyridine; dmap at 20 - 100℃; for 17h; Inert atmosphere;	84.4%
With pyridine; dmap at 80℃; for 5h;	81%

: 65956-63-0
stearyl 2-trimethylammonioethyl phosphate

: 50-91-9
5-Fluoro-2'-deoxyuridine

: 86976-76-3
Phosphoric acid (2R,3S,5R)-5-(5-fluoro-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-3-hydroxy-tetrahydro-furan-2-ylmethyl ester octadecyl ester

Conditions

Conditions	Yield
With phospholipase D from Streptomyces sp. AA 586 In chloroform; water at 45℃; for 6h; sodium acetate buffer, CaCl2, pH 5.8;	84%

: 100-11-8
1-bromomethyl-4-nitro-benzene

: 50-91-9
5-Fluoro-2'-deoxyuridine

: 98653-18-0
3-(p-nitrobenzyl)-2'-deoxy-5-fluorouridine

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide for 2h; Ambient temperature;	84%

: 65-85-0
benzoic acid

: 50-91-9
5-Fluoro-2'-deoxyuridine

: 2,3'-anhydro-5'-O-benzoyl-5-fluoro-2'-deoxvuridine

Conditions

Conditions	Yield
With di-isopropyl azodicarboxylate; triphenylphosphine In N,N-dimethyl-formamide for 0.75h;	84%

: 14243-64-2
(triphenylphosphine)gold(I) chloride

: 50-91-9
5-Fluoro-2'-deoxyuridine

: (5-fluoro-2'-deoxyuridinato-N3)(triphenylphosphine)gold(I)

Conditions

Conditions	Yield
With KOH In tetrahydrofuran; water under argon; gold complex, ligand and KOH were dissolved in H2O/THF; stirring at 50-60°C; precipitation by evaporation of THF; filtered off; recrystallization from THF with addition of diethylether; elem.anal., IR, NMR;	83.8%

: 6069-36-9
2-chloro-1,3-dimethyl-1,3,2-diazaphospholidine

: 50-91-9
5-Fluoro-2'-deoxyuridine

: 96502-21-5
2'-deoxy-5-fluoro-3',5'-bis-O-(1,3-dimethyl-1,3-diaza-2-phosphacyclopentan-2-yl)uridine

Conditions

Conditions	Yield
With triethylamine In chloroform at 0 - 20℃; for 1h;	83%

: vinyl 2-butenoate

: 50-91-9
5-Fluoro-2'-deoxyuridine

A: 1118767-44-4
5'-O-crotonyl-FUdR

B: 1072440-07-3
3'-O-crotonyl-FUdR

C: 1072440-08-4
3',5'-di-O-crotonyl-FUdR

Conditions

Conditions	Yield
With PSL-C; 1-n-butyl-2,3-dimethylimidazolium hexafluorophosphate In tetrahydrofuran at 50℃; for 43h; Reactivity; Time; Temperature; regioselective reaction;	A n/a B 83% C n/a

...Expand

: 58479-61-1
tert-butylchlorodiphenylsilane

: 50-91-9
5-Fluoro-2'-deoxyuridine

: 1-((2R,4S,5R)-5-(((tert-butyldiphenylsilyl)oxy)methyl)-4-hydroxytetrahydrofuran-2-yl)-5-fluoropyrimidine-2,4(1H,3H)-dione

Conditions

Conditions	Yield
With dmap; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃;	83%
With 1H-imidazole In N,N-dimethyl-formamide at 20℃; for 12h;	80%

: 108-05-4
vinyl acetate

: 50-91-9
5-Fluoro-2'-deoxyuridine

A: 2823-52-1
5'-O-acetyl-floxuridine

B: 7207-56-9, 110522-47-9
Acetic acid (2R,3S)-2-acetoxymethyl-5-((S)-5-fluoro-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester

C: 2059-38-3
3′-O-acetyl-5-fluoro-2′-deoxyuridine

Conditions

Conditions	Yield
PS (Pseudomonas sp. lipase) In 1,4-dioxane	A 8.1% B 8.5% C 82%
PPL (Porcine pancreas lipase) In 1,4-dioxane	A 49.3% B 0.4% C 25.7%

...Expand

: 18162-48-6
tert-butyldimethylsilyl chloride

: 50-91-9
5-Fluoro-2'-deoxyuridine

: 129816-30-4
5'-O-(tert-butyldimethylsilyl)-2'-deoxy-5-fluorouridine

Conditions

Conditions	Yield
With 1H-imidazole; dmap In N,N-dimethyl-formamide at 25℃; for 1h;	82%
With 1H-imidazole In N,N-dimethyl-formamide at -30℃; for 5.5h;	77%
With pyridine; 1H-imidazole at 20℃; for 24h; Inert atmosphere;	76%
With triethylamine In N,N-dimethyl-formamide at 0 - 20℃; for 12h;
With 1H-imidazole; dmap In N,N-dimethyl-formamide at 20℃; for 4h;

: 110-91-8
morpholine

: 7148-74-5
2-Bromopropionyl chloride

: 50-91-9
5-Fluoro-2'-deoxyuridine

: 80667-47-6
5'-O-(2-morpholinopropionyl)-2'-deoxy-5-fluorouridine

Conditions

Conditions	Yield
In 1,4-dioxane; pyridine; methanol; dichloromethane	82%

...Expand

: 397249-28-4
vinyl 2-ethylhexanoate

: 50-91-9
5-Fluoro-2'-deoxyuridine

A: 1118767-25-1
3'-O-(2-ethylhexanoyl)-FUdR

B: 1118767-43-3
5'-O-(2-ethylhexanoyl)-FUdR

Conditions

Conditions	Yield
With PSL-C; 1-n-butyl-2,3-dimethylimidazolium hexafluorophosphate In tetrahydrofuran at 50℃; for 90h; Reactivity; Temperature; Time; regioselective reaction;	A 82% B n/a

...Expand

: 1608-67-9
2-acetoxytetrahydrofuran

: 10416-59-8
N,O-bis-(trimethylsilyl)-acetamide

: 50-91-9
5-Fluoro-2'-deoxyuridine

: 103782-09-8
2'-deoxy-5-fluoro-3-(2-tetrahydrofuranyl)uridine

Conditions

Conditions	Yield
With acetic acid; triethylamine; tin(IV) chloride In methanol; dichloromethane	81.7%

...Expand

Floxuridine Chemical Properties

IUPAC Name: 5-Fluoro-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dione
Synonyms of 2'-Deoxy-5-fluorouridine (CAS NO.50-91-9): 1-(2-Deoxy-beta-D-ribofuranosyl)-5-fluorouracil ; 1-beta-D-2'-Deoxyribofuranosyl-5-flurouracil ; 1beta-D-2'-Deoxyribofuranosyl-5-flurouracil ; 5-24-06-00291 (Beilstein Handbook Reference) ; 5-FUDR ; 5-FdUrd ; 5-Fluor-1-(beta-2'-deoxyribofuranosyl)pyrimidin-2,4(1H,3H)-dion ; 5-Fluor-1-(beta-2'-deoxyribofuranosyl)pyrimidin-2,4(1H,3H)-dion [Czech] ; 5-Fluoro-2-desoxyuridine ; 5-Fluorodeoxyuridine ; 5-Fluorouracil 2'-deoxyriboside ; 5-Fluorouracil deoxyriboside ; AI3-50691 ; BRN 0090221 ; Deoxyfluorouridine ; EINECS 200-072-5; Floxiridina ; Floxiridina [INN-Spanish] ; Floxuridin ; Floxuridine ; Floxuridinum ; Floxuridinum [INN-Latin] ; Fluorodeoxyuridine ; Fluoruridine deoxyribose ; HSDB 3227 ; NSC 27640 ; NSC-27640 ; Ro 5-0360 ; UNII-039LU44I5M ; Uridine, 2'-deoxy-5'-fluoro- ; beta-5-Fluoro-2'-deoxyuridine
CAS NO: 50-91-9
Classification Code: Antimetabolites ; Antimetabolites, antineoplastic ; Antineoplastic ; Antineoplastic Agents ; Antiviral ; Drug / Therapeutic Agent ; Human Data ; Mutation data ; Noxae ; Reproductive Effect
Molecular Formula: C₉H₁₁FN₂O₅
Molecular Weight: 246.1924
Molecular Structure:

Melting Point: 148 °C
H bond acceptors: 7
H bond donors: 3
Freely Rotating Bonds: 4
Polar Surface Area: 68.31 Å²
Index of Refraction: 1.608
Molar Refractivity: 51.94 cm³
Molar Volume: 150 cm³
Surface Tension: 72.3 dyne/cm
Density: 1.64 g/cm³

Floxuridine Uses

2'-Deoxy-5-fluorouridine (CAS NO.50-91-9) can be used as antineoplastic agents.It is applicable in the treatment of liver cancer, gastrointestinal cancer, breast cancer and head and neck cancer. It may make bone marrow suppression. Local gastrointestinal reactions and skin reactions similar to side effects and fluorouracil. Also it can have the phenomenon which alkaline phosphatase, serum transaminases, serum bilirubin and lactate dehydrogenase increased .

Floxuridine Production

The production methods of 2'-Deoxy-5-fluorouridine (CAS NO.50-91-9) is methyl -2 - deoxy-D-glucoside hydrolyzed by P-Toluoyl chlorid and acetic acid - hydrochloric acid ,make a methoxy substituted by chlorine. Then the product is of condensation with 1 -acetyl-oxygen Mercury -5 - fluorouracil, and the condensation product removed benzoyl- A by hydrolyzed and derived the product.

Floxuridine Toxicity Data With Reference

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
human	TDLo	intravenous	5mg/kg/14D-C (5mg/kg)	GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA" GASTROINTESTINAL: NAUSEA OR VOMITING GASTROINTESTINAL: OTHER CHANGES	Cancer Vol. 34, Pg. 972, 1974.
mouse	LD50	intraperitoneal	650mg/kg (650mg/kg)	GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA" GASTROINTESTINAL: NAUSEA OR VOMITING	Proceedings of the Society for Experimental Biology and Medicine. Vol. 97, Pg. 470, 1958.
mouse	LD50	oral	147mg/kg (147mg/kg)		Progress Report for Contract No. NIH-NCI-E-C-72-3252, Submitted to the National Cancer Institute by Litton Bionetics, Inc. Vol. NCI-E-C-72-3252, Pg. 1973,
mouse	LD50	unreported	550mg/kg (550mg/kg)		Cancer Research. Vol. 46, Pg. 2703, 1986.
rat	LD50	intraperitoneal	1600mg/kg (1600mg/kg)		Clinical Proceedings of the Children's Hospital of the District of Columbia. Vol. 18, Pg. 307, 1962.
rat	LD50	oral	215mg/kg (215mg/kg)		Progress Report for Contract No. NIH-NCI-E-C-72-3252, Submitted to the National Cancer Institute by Litton Bionetics, Inc. Vol. NCI-E-C-72-3252, Pg. 1973,
women	TDLo	parenteral	173mg/kg/82W- (173mg/kg)	SKIN AND APPENDAGES (SKIN): "DERMATITIS, ALLERGIC: AFTER SYSTEMIC EXPOSURE"	Journal of the National Medical Association. Vol. 79, Pg. 669, 1987.

Floxuridine Consensus Reports

EPA Genetic Toxicology Program.

Floxuridine Safety Profile

Hazard Codes 2'-Deoxy-5-fluorouridine (CAS NO.50-91-9): Harmful Xn, Toxic T, Irritant Xi
Risk Statements: 68-36/37/38-40-20/21/22
R68: Possible risk of irreversible effects.
R36/37/38: Irritating to eyes, respiratory system and skin.
R40: Limited evidence of a carcinogenic effect.
R20/21/22: Harmful by inhalation, in contact with skin and if swallowed.
Safety Statements: 22-36/37/39-26
S22: Do not breathe dust.
S36/37/39: Wear suitable protective clothing, gloves and eye/face protection.
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
RIDADR: UN 2811 6.1/PG 3
WGK Germany: 3
RTECS: YU7525000
F: 10-23
Hazard Note: Toxic
HazardClass: 6.1
PackingGroup: III
Poison by ingestion. Moderately toxic by intraperitoneal route. An experimental teratogen. Other experimental reproductive effects. Human systemic effects: hypermotility, diarrhea, nausea, vomiting and other gastrointestinal effects, allergic dermatitis, and bone marrow changes. Human mutation data reported. When heated to decomposition it emits very toxic fumes of F⁻ and NO_x .

Product Name

Floxuridine

Synthetic route

Floxuridine Chemical Properties

Floxuridine Uses

Floxuridine Production

Floxuridine Toxicity Data With Reference

Floxuridine Consensus Reports

Floxuridine Safety Profile

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