Gemcitabine supplier | CasNO.95058-81-4

Name
Gemcitabine
EINECS 619-100-6
CAS No. 95058-81-4
Article Data50
CAS DataBase
Density 1.84 g/cm³
Solubility
Melting Point 168.64 °C
Formula C₉H₁₁F₂N₃O₄
Boiling Point 482.7 °C at 760 mmHg
Molecular Weight 263.201
Flash Point 245.7 °C
Transport Information
Appearance white powder
Safety 25-26-36/37-53
Risk Codes 21-36/38-46-62-63
Molecular Structure
Hazard Symbols Xn,Xi
Synonyms 4-amino-1-[(2R,4R,5R)-3,3-difluoro-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidin-2-one;Cytidine, 2-deoxy-2,2-difluoro-2-Deoxy-.beta.-D-2,2-difluorocytidine;Gemcitabine [USAN:BAN:INN];DDFC;LY 188011;LY188011 hydrochloride;Cytosine, 1-(2-deoxy-2,2-difluoro-beta-D-erythro-pentofuranosyl)-;Gemcitabine hydrochloride [USAN];LY188011;2-Deoxy-2,2-difluorocytidine monohydrochloride;Gemzar;2(1H)-Pyrimidinone, 4-amino-1-(2-deoxy-2,2-difluoro-D-erythro-pentofuranosyl)-;2'-Deoxy-2',2'-Difluorocytidine;2',2'-Difluorodeoxycytidine(Gemcitabine base);Cytidine, 2'-deoxy-2',2'-difluoro-;
PSA 110.60000
LogP -0.70740

Synthetic route

: 942288-40-6
(2R,3R,5R)-5-(4-amino-2-oxopyrimidine-1(2H)-yl)-4,4-difluoro-2-((3-fluorobenzoyloxy)methyl)tetrahydrofuran-3-yl 3-fluorobenzoate

: 95058-81-4
gemcitabine

Conditions

Conditions	Yield
With ammonia; water at 20℃; for 3h;	100%
With methanol; ammonia; water at 20℃; for 3h;	100%

: 134790-39-9
(2'-deoxy-2',2'-difluorocytidine)-3',5'-dibenzoate

: 95058-81-4
gemcitabine

Conditions

Conditions	Yield
With ammonium hydroxide In methanol at 20℃; for 3h;	82.7%
With sodium t-butanolate In methanol at 20℃; for 2h;

: 896109-84-5
1-(2'-deoxy-2',2'-difluoro-5-benzoyl-3-(4-phenyl)benzoyl-β-D-arabinofuranosyl)-4-aminopyrimidine-2-one

: 95058-81-4
gemcitabine

Conditions

Conditions	Yield
With ammonia In methanol at 20℃; for 12h; Product distribution / selectivity;	76.9%

: 1-(5'-O-benzoyl-2'-deoxy-2',2'-difluoro-3-O-(p-phenylbenzoyl)-D-ribofuranosyl)-4-aminopyrimidin-2-one

: 95058-81-4
gemcitabine

Conditions

Conditions	Yield
With ammonia In methanol at 20℃; Product distribution / selectivity;	72.6%
With ammonia In methanol at 20℃; Product distribution / selectivity;	72.6%
With ammonia; water In methanol at 20℃; for 12h;	71%
With ammonia In methanol at 20℃; Product distribution / selectivity;

: (2R,3R)-5-(4-acetamido-2-oxopyrimidin-1(2H)-yl)-2-((benzoyloxy)methyl)-4,4-difluorotetrahydrofuran-3-yl benzoate

: 95058-81-4
gemcitabine

Conditions

Conditions	Yield
With Amberlite IRA 400, OH-form In methanol at 40 - 45℃; for 36h; Product distribution / selectivity;	71%
With ammonia In methanol; water at 20℃; for 24h; Product distribution / selectivity;

: C31H25F2N3O7

: 95058-81-4
gemcitabine

Conditions

Conditions	Yield
With ammonia In methanol Product distribution / selectivity;	63%
With ammonia In methanol for 8h; Product distribution / selectivity;	63%
With ammonia In methanol

: 1018907-93-1
2-amino-N-(1-((2R,4R,5R)-3,3-difluoro-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-2-oxo-1,2-dihydropyrimidin-4-yl)acetamide trifluoroacetic acid

A: 1018908-06-9
C11H14F2N4O5

B: 95058-81-4
gemcitabine

Conditions

Conditions	Yield
With sodium hydrogencarbonate In methanol	A 51% B n/a

: 1260238-57-0
2'-deoxy-2',2'-difluoro-3',5'-di-O-(triisopropylsilyl)cytidine

A: 95058-85-8
α-1-(2-oxo-4-amino-1,2-dihydropyrimidin-1-yl)-2-deoxy-2,2-difluororibose

B: 95058-81-4
gemcitabine

Conditions

Conditions	Yield
With tetramethylammonium fluoride; acetic acid In N,N-dimethyl-formamide at 20℃; stereoselective reaction;	A 42% B 36%
With tetramethylammonium fluoride; acetic acid In N,N-dimethyl-formamide at 20℃;

: 1018908-14-9
C2HF3O2*C14H18F2N4O5

A: 1018908-15-0
C14H18F2N4O5

B: 95058-81-4
gemcitabine

Conditions

Conditions	Yield
With sodium hydrogencarbonate In methanol	A 38% B n/a

: 18027-23-1
bis(trimethylsilyl)-N-acetylcytosine

: 103882-89-9
3,5-bis-O-(tert-butyldimethylsilyl)-1-O-(methanesulfonyl)-2-deoxy-2,2-difluororibose

A: 95058-85-8
α-1-(2-oxo-4-amino-1,2-dihydropyrimidin-1-yl)-2-deoxy-2,2-difluororibose

B: 95058-81-4
gemcitabine

Conditions

Conditions	Yield
Multistep reaction;

...Expand

: 952408-92-3
1-[2'-deoxy-2',2'-difluoro-3',5'-bis(tert-butyldiphenylsilyloxy)-ribofuranosyl]-cytosine

A: 95058-85-8
α-1-(2-oxo-4-amino-1,2-dihydropyrimidin-1-yl)-2-deoxy-2,2-difluororibose

B: 95058-81-4
gemcitabine

Conditions

Conditions	Yield
With ammonium fluoride In methanol at 65℃; for 3h;

: 122111-03-9
gemcitabine hydrochloride

: 95058-81-4
gemcitabine

Conditions

Conditions	Yield
With potassium carbonate In ethanol; dichloromethane at 20℃;
With triethylamine In N,N-dimethyl-formamide at 20℃; for 0.0833333h;
Multi-step reaction with 4 steps 1: 1H-imidazole / N,N-dimethyl-formamide / 2.5 h / 20 °C 2: pyridine / tetrahydrofuran / 1 h / 4 °C 3: tetrabutyl ammonium fluoride / tetrahydrofuran / 20 °C 4: Pd0-functionalized resin / aq. phosphate buffer / 37 °C / pH 7.4 View Scheme
Multi-step reaction with 4 steps 1: 1H-imidazole / N,N-dimethyl-formamide / 2.5 h / 20 °C 2: pyridine / tetrahydrofuran / 20 °C 3: tetrabutyl ammonium fluoride / tetrahydrofuran / 20 °C 4: Pd0-functionalized resin / aq. phosphate buffer / 37 °C / pH 7.4 View Scheme
Multi-step reaction with 4 steps 1: 1H-imidazole / N,N-dimethyl-formamide / 2.5 h / 20 °C 2: pyridine / tetrahydrofuran / 48 h / 20 °C 3: tetrabutyl ammonium fluoride / tetrahydrofuran / 3 h / 20 °C 4: Pd0-functionalized resin / aq. phosphate buffer / 37 °C / pH 7.4 View Scheme

: 142816-70-4
N4-benzoyl-2'-deoxy-2',2'-difluorocytidine

: 95058-81-4
gemcitabine

Conditions

Conditions	Yield
With pyridine; ammonium hydroxide In water at 37℃; for 18h; Kinetics;

: 861445-90-1
C13H15F2N3O6

A: 95058-85-8
α-1-(2-oxo-4-amino-1,2-dihydropyrimidin-1-yl)-2-deoxy-2,2-difluororibose

B: 95058-81-4
gemcitabine

Conditions

Conditions	Yield
With sodium ethanolate In isopropyl alcohol for 1 - 6h; Heating / reflux;

: 892128-60-8
N-(1-((2R,4R,5R)-3,3-difluoro-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-2-oxo-1,2-dihydropyrimidin-4-yl)-2-propylpentanamide

: 95058-81-4
gemcitabine

Conditions

Conditions	Yield
With water; CD-1 mouse small intestinal homogenate for 6h; pH=7.5; Conversion of starting material; Aqueous acetate buffer; Enzymatic reaction;
With water; CD-1 mouse post-mitochondrial liver (S9) homogenate for 6h; pH=8.0; Conversion of starting material; Aqueous phosphate buffer; Enzymatic reaction;
With water; beagle dog post-mitochondrial liver (S9) homogenate for 6h; pH=8.0; Conversion of starting material; Aqueous phosphate buffer; Enzymatic reaction;

: 1-(5'-O-benzoyl-2'-deoxy-2',2'-difluoro-3-O-(p-phenylbenzoyl)-D-ribofuranosyl)-4-aminopyrimidin-2-one

A: 95058-85-8
α-1-(2-oxo-4-amino-1,2-dihydropyrimidin-1-yl)-2-deoxy-2,2-difluororibose

B: 95058-81-4
gemcitabine

Conditions

Conditions	Yield
With ammonia In methanol at 20℃; Product distribution / selectivity;
With ammonia In methanol at 20℃;
With ammonia In methanol at 20℃; for 10h; Product distribution / selectivity;

: N4-(1-(5-nitrothien-2-yl)ethyl)oxycarbonyl-2',2'-difluoro-2'-deoxycytidine

: 95058-81-4
gemcitabine

Conditions

Conditions	Yield
In water; isopropyl alcohol G-values; Irradiation;

: N4-(2-nitro-1-methylimidazol-5-yl)methoxycarbonyl-2',2'-difluoro-2'-deoxycytidine

: 95058-81-4
gemcitabine

Conditions

Conditions	Yield
In water; isopropyl alcohol G-values; Irradiation;

: N4-(5-nitrothien-2-yl)methoxycarbonyl-2',2'-difluoro-2'-deoxycytidine

: 95058-81-4
gemcitabine

Conditions

Conditions	Yield
In water; isopropyl alcohol G-values; Irradiation;

: 3',5'-bis(tert-butyldiphenylsilyloxy)-2',2'-difluoro-2'-deoxycytidine

: 95058-81-4
gemcitabine

Conditions

Conditions	Yield
With tetrabutyl ammonium fluoride In tetrahydrofuran at 15 - 30℃; for 5.33333h;

: 2',2'-difluoro-2'-deoxy-N-acetylcytidine-3',5'-dibenzoate

A: 95058-85-8
α-1-(2-oxo-4-amino-1,2-dihydropyrimidin-1-yl)-2-deoxy-2,2-difluororibose

B: 95058-81-4
gemcitabine

Conditions

Conditions	Yield
With methanol; ammonia at -5 - 5℃; for 8 - 10h;

: 1147119-18-3
(2R,3R,5R)-5-(4-amino-2-oxopyrimidin-1(2H)-yl)-4,4-difluoro-2-(hydroxymethyl)tetrahydrofuran-3-yl benzoate hydrochloride

: 95058-81-4
gemcitabine

Conditions

Conditions	Yield
With ammonia In methanol Product distribution / selectivity;
With methanol; 2,2,2-trifluoroethanol; potassium carbonate Product distribution / selectivity;

: 103882-84-4
2’-deoxy-2’,2’-difluoro-cytidine

: 95058-81-4
gemcitabine

Conditions

Conditions	Yield
With ammonia In water Resolution of racemate;

: 1155863-81-2
C23H19F2N3O6

A: 95058-85-8
α-1-(2-oxo-4-amino-1,2-dihydropyrimidin-1-yl)-2-deoxy-2,2-difluororibose

B: 95058-81-4
gemcitabine

Conditions

Conditions	Yield
With sodium methylate

: 2-deoxy-2,2-difluoro-3,5-di-O-(triisopropylsilyl)-D-ribofuranose

A: 95058-85-8
α-1-(2-oxo-4-amino-1,2-dihydropyrimidin-1-yl)-2-deoxy-2,2-difluororibose

B: 95058-81-4
gemcitabine

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: triethylamine / dichloromethane / 3 h / 0 - 20 °C / Inert atmosphere 2.1: trimethylsilyl trifluoromethanesulfonate / 1,2-dichloro-ethane / 0.5 h / 20 °C 2.2: Reflux 3.1: tetramethylammonium fluoride; acetic acid / N,N-dimethyl-formamide / 20 °C View Scheme
Multi-step reaction with 3 steps 1.1: methanesulfonyl chloride; triethylamine / dichloromethane 2.1: trimethylsilyl trifluoromethanesulfonate / 1,2-dichloro-ethane / 0.5 h / 20 °C 2.2: Reflux 3.1: tetramethylammonium fluoride; acetic acid / N,N-dimethyl-formamide / 20 °C View Scheme

: 1173700-36-1
1-methylsulfonyl-2-deoxy-2,2-difluoro-3,5-di-O-(triisopropylsilyl)-D-ribofuranose

A: 95058-85-8
α-1-(2-oxo-4-amino-1,2-dihydropyrimidin-1-yl)-2-deoxy-2,2-difluororibose

B: 95058-81-4
gemcitabine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: trimethylsilyl trifluoromethanesulfonate / 1,2-dichloro-ethane / 0.5 h / 20 °C 1.2: Reflux 2.1: tetramethylammonium fluoride; acetic acid / N,N-dimethyl-formamide / 20 °C View Scheme
Multi-step reaction with 2 steps 1.1: trimethylsilyl trifluoromethanesulfonate / 1,2-dichloro-ethane / 0.5 h / 20 °C 1.2: Reflux 2.1: tetramethylammonium fluoride; acetic acid / N,N-dimethyl-formamide / 20 °C View Scheme

: C4H11N*C9H11F2N3O4*C72H72N4O12*H(1+)

A: C4H11N*C72H72N4O12*H(1+)

B: 95058-81-4
gemcitabine

Conditions

Conditions	Yield
at 20℃; under 9.0009E-09 Torr; Kinetics; Fourier-Transform Ion Cyclotron Resonance mass spectrometer;

: C4H11N*C9H11F2N3O4*C72H72N4O12*H(1+)

A: C4H11N*C72H72N4O12*H(1+)

B: 95058-81-4
gemcitabine

Conditions

Conditions	Yield
at 20℃; under 9.75098E-09 Torr; Kinetics; Fourier-Transform Ion Cyclotron Resonance mass spectrometer;

: C4H11N*C9H11F2N3O4*C72H72N4O12*H(1+)

A: C4H11N*C72H72N4O12*H(1+)

B: 95058-81-4
gemcitabine

Conditions

Conditions	Yield
at 20℃; under 3.0003E-08 Torr; Kinetics; Fourier-Transform Ion Cyclotron Resonance mass spectrometer;

: 69304-37-6
1,3-Dichloro-1,1,3,3-tetraisopropyldisiloxane

: 95058-81-4
gemcitabine

: 1254062-21-9
4-amino-1-((6aR,8R,9aR)-9,9-difluoro-2,2,4,4-tetraisopropyltetrahydro-6H-furo[3,2-f] [1,3,5,2,4]trioxadisilocin-8-yl)pyrimidin-2(1H)-one

Conditions

Conditions	Yield
With pyridine at 20℃; for 4h;	100%
With pyridine at 20℃; for 48h;	84%
With 1H-imidazole In N,N-dimethyl-formamide at 20℃; for 16h; Inert atmosphere;	82.3%

: 18162-48-6
tert-butyldimethylsilyl chloride

: 95058-81-4
gemcitabine

: 688009-09-8
4-amino-1-((2R,4R,5R)-4-((tert-butyldimethylsilyl)oxy)-5-(((tert-butyldimethylsilyl)oxy)methyl)-3,3-difluoro-tetrahydrofuran-2-yl)pyrimidin-2(1H)-one

Conditions

Conditions	Yield
With 1H-imidazole In N,N-dimethyl-formamide at 20℃; Cooling with ice; Inert atmosphere;	99%
With 1H-imidazole at 20℃;	97.1%
With 1H-imidazole In N,N-dimethyl-formamide at 20℃; Solvent; Reagent/catalyst;	95%

: 541-41-3
chloroformic acid ethyl ester

: 95058-81-4
gemcitabine

: 155968-14-2
1-[(2R,4R,5R)-3,3-difluoro-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2-dihydro-4-(ethoxycarbonylamino)pyrimidin-2-one

Conditions

Conditions	Yield
In ethyl acetate; acetonitrile for 3h; Inert atmosphere; Reflux;	98.31%

: 24424-99-5
di-tert-butyl dicarbonate

: 95058-81-4
gemcitabine

: 250698-51-2
(2R,3R,5R)-5-(4-amino-2-oxopyrimidin-1(2H)-yl)-4,4-difluoro-2-(hydroxymethyl)tetrahydrofuran-3-yl tert-butyl carbonate

Conditions

Conditions	Yield
With sodium carbonate In 1,4-dioxane; water at 20℃; for 50h;	94%
With sodium carbonate In water at 20℃; for 30h;	89%
With sodium carbonate In 1,4-dioxane; water at 20℃; for 72h;	88%

: 110-94-1
1,5-pentanedioic acid

: 95058-81-4
gemcitabine

: 80029-43-2, 123333-53-9
1-hydroxybenzotriazol-hydrate

: 5-((1-((2R,4R,5R)-3,3-difluoro-4-hydroxy-5-(hydroxymethyl) tetrahydrofuran-2-yl)-2-oxo-1,2-dihydro-pyrimidin-4-yl)amino)-5-oxo-pentanoic acid

Conditions

Conditions	Yield
With 4-methyl-morpholine	94%

...Expand

: 95058-81-4
gemcitabine

: 122111-03-9
gemcitabine hydrochloride

Conditions

Conditions	Yield
With hydrogenchloride In water; isopropyl alcohol at 20 - 70℃;	93.4%
With hydrogenchloride In water; acetone at 20℃; for 2h; Product distribution / selectivity;	91.5%
With hydrogenchloride In isopropyl alcohol at 0 - 5℃; for 2h; pH=2;	90%

: 24424-99-5
di-tert-butyl dicarbonate

: 95058-81-4
gemcitabine

: 250698-52-3
3′,5′-O-bis(tert-butoxycarbonyl)-gemcitabine

Conditions

Conditions	Yield
Stage #1: gemcitabine With potassium hydroxide In water at 20℃; for 1h; Stage #2: di-tert-butyl dicarbonate In 1,4-dioxane; water at 20℃; for 1h;	93%
Stage #1: gemcitabine With potassium hydroxide In water for 1h; Stage #2: di-tert-butyl dicarbonate In 1,4-dioxane; water at 20℃; for 2.67h;	90%
With potassium hydroxide In 1,4-dioxane

: 98-88-4
benzoyl chloride

: 95058-81-4
gemcitabine

: 1445381-44-1
(2R,3R,5R)-5-(4-benzamido-2-oxopyrimidin-1(2H)-yl)-2-((benzoyloxy)methyl)-4,4-difluorotetrahydrofuran-3-yl benzoate

Conditions

Conditions	Yield
With pyridine; dmap at 0 - 20℃; for 3.5h; Inert atmosphere;	93%

: 76-83-5
trityl chloride

: 95058-81-4
gemcitabine

: 5'-Tr-gemcytabine

Conditions

Conditions	Yield
With triethylamine In pyridine at 20℃; for 6h; Inert atmosphere; Cooling with ice; regioselective reaction;	91.2%

: 45289-91-6
Azelaic anhydride

: 95058-81-4
gemcitabine

: 5-((1-((2R,4R,5R)-3,3-difluoro-4-hydroxy-5-(hydroxymethyl) tetrahydrofuran-2-yl)-2-oxo-1,2-dihydro-pyrimidin-4-yl)amino)-5-oxo-nonanoic acid

Conditions

Conditions	Yield
	91%

: 501-53-1
benzyl chloroformate

: 95058-81-4
gemcitabine

: 138685-83-3
4-(benzyloxycarbonylamino)-1-(2-deoxy-2,2-difluoro-β-D-erythro-pentofuranosyl)pyrimidin-2(1H)-one

Conditions

Conditions	Yield
Stage #1: gemcitabine With pyridine; chloro-trimethyl-silane at 4 - 20℃; for 1.5h; Inert atmosphere; Stage #2: benzyl chloroformate In methanol at 20℃; Inert atmosphere;	91%

: 95058-81-4
gemcitabine

: 95058-82-5
4-amino-1-(2-deoxy-2,2’-difluoro-β-D-erythro-pentofuranosyl)-5-iodopyrimidin-2(1H)-one

Conditions

Conditions	Yield
With hydrogen iodide; iodine In tetrachloromethane; ethanol; water at 45℃; for 16h;	90%

: 95058-81-4
gemcitabine

: 98-59-9
p-toluenesulfonyl chloride

: 1519060-68-4
N-(1-((2R,4R,5R)-3,3-difluoro-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-2-oxo-1,2-dihydropyrimidin-4-yl)-4-methylbenzenesulfonamide

Conditions

Conditions	Yield
With pyridine; chloro-trimethyl-silane; ammonia In methanol Inert atmosphere;	90%
With pyridine; chloro-trimethyl-silane at 20℃; for 2h; Inert atmosphere;	83%

: 5809-91-6
vinyl myristate

: 95058-81-4
gemcitabine

: O5’-tetradecanoyl-2',2'-difluoro-2'-deoxycytidine

Conditions

Conditions	Yield
With pyridine; lipase B Candida antarctica In hexane at 50℃; for 6h; Enzymatic reaction;	89%

: N-(pyridin-4-carbonyl)-D-Ala-L-Proline

: 95058-81-4
gemcitabine

: C23H26F2N6O7

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; HATU In N,N-dimethyl-formamide	87%

: 24424-99-5
di-tert-butyl dicarbonate

: 95058-81-4
gemcitabine

: tert-butyl [1-((2R,4R,5R)-3,3-difluoro-4-hydroxy-5-hydroxymethyl-tetrahydrofuran-2-yl)-2-oxo-1,2-dihydro-pyrimidin-4-yl]-carbamate

Conditions

Conditions	Yield
In N,N-dimethyl-formamide at 50℃; for 18h;	86%
In N,N-dimethyl-formamide at 50℃; for 18h;	86%

: (R)-2-((R)-(2,3,4,5,6-pentafluorophenoxy)phenoxyphosphorylamino)propionic acid isopropyl ester

: 95058-81-4
gemcitabine

: C21H27F2N4O8P

Conditions

Conditions	Yield
In tetrahydrofuran at 0℃;	85%

: 1334513-02-8
(S)-2-[((S)-(2,3,4,5,6-pentafluorophenoxy)(phenoxy)phosphoryl)amino]propionic acid isopropyl ester

: 95058-81-4
gemcitabine

: isopropyl ((S)-(((2R,3R,5R)-5-(4-amino-2-oxopyrimidin-1(2H)-yl)-4,4-difluoro-3-hydroxytetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)-L-alaninate

Conditions

Conditions	Yield
With pyridine; dimethylaluminum chloride In hexane at 0 - 20℃; for 22h; Inert atmosphere; diastereoselective reaction;	83%

: 28920-43-6
(fluorenylmethoxy)carbonyl chloride

: 95058-81-4
gemcitabine

: (9H-fluoren-9-yl)methyl (1-((2R,4R,5R)-3,3-difluoro-4-hydroxy-5-(hydroxymethyl)-tetrahydrofuran-2-yl)-2-oxo-1,2-dihydropyrimidin-4-yl)carbamate

Conditions

Conditions	Yield
Stage #1: gemcitabine With pyridine; chloro-trimethyl-silane for 0.333333h; Stage #2: (fluorenylmethoxy)carbonyl chloride In water for 2.5h;	80.9%
Stage #1: gemcitabine With 1H-imidazole; dmap; tert-butyldimethylsilyl chloride In N,N-dimethyl-formamide at 20℃; Stage #2: (fluorenylmethoxy)carbonyl chloride With pyridine In dichloromethane at 20℃; Stage #3: With pyridine hydrogenfluoride In tetrahydrofuran at 20℃; for 24h;	79.4%

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

: 95058-81-4
gemcitabine

: 1421929-71-6
C30H29F2N3O6

Conditions

Conditions	Yield
With pyridine at 20℃; for 4h;	80%
With pyridine at 0 - 20℃; for 4h;	64%
With pyridine at 0 - 20℃; for 4h;	39%

: (2S)-2-[(S)-(2,3,4,5,6-pentafluorophenoxy)-phenoxy-phosphorylamino]propionic acid benzyl ester

: 95058-81-4
gemcitabine

: benzyl ((S)-(((2R,3R,5R)-5-(4-amino-2-oxopyrimidin-1(2H)-yl)-4,4-difluoro-3-hydroxytetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)-L-alaninate

Conditions

Conditions	Yield
With pyridine; dimethylaluminum chloride In hexane at 0 - 20℃; for 20h; Inert atmosphere; diastereoselective reaction;	80%

: 807370-86-1
C18H26O13

: 95058-81-4
gemcitabine

: C27H35F2N3O16

Conditions

Conditions	Yield
Stage #1: C18H26O13 With 1-hydroxy-pyrrolidine-2,5-dione; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 2h; Inert atmosphere; Stage #2: gemcitabine In N,N-dimethyl-formamide at 20℃; for 24h; Inert atmosphere;	80%

: 95058-81-4
gemcitabine

: 116371-67-6
Gemcitabine monophosphate

Conditions

Conditions	Yield
Stage #1: gemcitabine With trichlorophosphate at 20℃; for 0.15h; Flow reactor; Green chemistry; Stage #2: With water at 20℃; Temperature; Flow reactor; Green chemistry; chemoselective reaction;	78%
With trimethyl phosphite; trichlorophosphate at -5℃; for 2h;	53%
With recombinant deoxyribonucleoside kinase AtdNK from Arabidopsis thaliana (ecotype Columbia); ATP In aq. buffer Kinetics; Concentration; Reagent/catalyst; Enzymatic reaction;
Multi-step reaction with 5 steps 1: pyridine / 4 h / 0 - 20 °C 2: pyridine / 2 h / 0 - 20 °C 3: toluene-4-sulfonic acid / dichloromethane / 2 h / 20 °C 4: 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile / 4 h / 20 °C 5: ammonium hydroxide View Scheme
Multi-step reaction with 7 steps 1: pyridine / 4 h / 0 - 20 °C 2: pyridine / 2 h / 0 - 20 °C 3: toluene-4-sulfonic acid / dichloromethane / 2 h / 20 °C 4: N-ethyl-N,N-diisopropylamine / dichloromethane 5: 1H-tetrazole; water / acetonitrile 6: pyridine; iodine; triethylamine; water 7: ammonium hydroxide View Scheme

: 2146-71-6
vinyl laurate

: 95058-81-4
gemcitabine

: O5'-dodecanoyl-2',2'-difluoro-2'-deoxycytidine

Conditions

Conditions	Yield
With pyridine; lipase B Candida antarctica In hexane at 50℃; for 6h; Enzymatic reaction;	76.9%

: C30H33N2O8S3(1-)

: 95058-81-4
gemcitabine

: C39H42F2N5O11S3(1-)

Conditions

Conditions	Yield
Stage #1: C30H33N2O8S3(1-) With N-ethyl-N,N-diisopropylamine In dimethyl sulfoxide at 20℃; for 0.5h; Stage #2: gemcitabine In dimethyl sulfoxide for 15h;	75%

: 108-30-5
succinic acid anhydride

: 95058-81-4
gemcitabine

: 1374587-08-2
N4-n-butyryl gemcitabine

Conditions

Conditions	Yield
With triethylamine In N,N-dimethyl-formamide at 60℃; Inert atmosphere;	75%

: 110-15-6
succinic acid

: 95058-81-4
gemcitabine

: N-(3-Carboxy-1-oxopropyl)-2'-deoxy-2',2'-difluorocytidine

Conditions

Conditions	Yield
Stage #1: succinic acid With thionyl chloride; triethylamine In 1,4-dioxane at 110℃; for 4h; Inert atmosphere; Stage #2: gemcitabine With triethylamine In N,N-dimethyl-formamide at 20℃; Inert atmosphere;	75%

Gemcitabine Specification

1. Introduction of Gemcitabine
Gemcitabine is one kind of white to light yellow powder. The IUPAC name of this chemical is 4-Amino-1-[(2R,4R,5R)-3,3-difluoro-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidin-2-one. It belongs to API;Antineoplastic drug, difluorine nucleoside analog. In addition, the Classification Code of it is Anti-Infective Agents; Antimetabolites; Antimetabolites, Antineoplastic; Antineoplastic; Antineoplastic Agents; Antiviral Agents; Enzyme Inhibitors; Immunologic Factors; Immunosuppressive Agents; Noxae; Radiation-Sensitizing Agents. Gemcitabine can soluble in water.

2. Properties of Gemcitabine
Physical properties about Gemcitabine are:
(1)Melting Point: 168.64 °C; (2)Boiling Point: 482.7 °C at 760 mmHg; (3)Flash Point: 245.7 °C; (4)Index of Refraction: 1.652; (5)Molar Refractivity: 52.06 cm³; (6)Molar Volume: 142.3 cm³; (7)Surface Tension: 65.3 dyne/cm; (8)Enthalpy of Vaporization: 86.16 kJ/mol; (9)Vapour Pressure: 2.41E-11 mmHg at 25 °C; (10)XLogP3: -1.5; (11)H-Bond Donor: 3; (12)H-Bond Acceptor: 7; (13)Rotatable Bond Count: 2; (14)Tautomer Count: 3; (15)Exact Mass: 263.071762; (16)MonoIsotopic Mass: 263.071762; (17)Topological Polar Surface Area: 108; (18)Heavy Atom Count: 18.

3. Structure Descriptors of Gemcitabine
(1)Canonical SMILES: C1=CN(C(=O)N=C1N)C2C(C(C(O2)CO)O)(F)F
(2)Isomeric SMILES: C1=CN(C(=O)N=C1N)[C@H]2C([C@@H]([C@H](O2)CO)O)(F)F
(3)InChI: InChI=1S/C9H11F2N3O4/c10-9(11)6(16)4(3-15)18-7(9)14-2-1-5(12)13-8(14)17/h1-2,4,6-7,15-16H,3H2,(H2,12,13,17)/t4-,6-,7-/m1/s1
(4)InChIKey: SDUQYLNIPVEERB-QPPQHZFASA-N

4. Toxicity of Gemcitabine

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
man	TDLo	intravenous	27mg/kg (27mg/kg)	LUNGS, THORAX, OR RESPIRATION: DYSPNEA LUNGS, THORAX, OR RESPIRATION: PLEURAL EFFUSION	Journal of Cancer Research and Clinical Oncology. Vol. 125, Pg. 637, 1999.

5. Safety information of Gemcitabine
Hazard Codes: Harmful Xn, Irritant Xi
Risk Statements: 21-36/38-46-62-63
R21:Harmful in contact with skin.
R36/38:Irritating to eyes and skin.
R46:May cause heritable genetic damage.
R62:Risk of impaired fertility.
R63:Possible risk of harm to the unborn child.
Safety Statements: 25-26-36/37-53
S25:Avoid contact with eyes.
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S36/37:Wear suitable protective clothing and gloves.
S53:Avoid exposure - obtain special instructions before use.
Human systemic effects When heated to decomposition it emits toxic vapors of NO_x and F⁻.

6. Uses of Gemcitabine
Gemcitabine (CAS NO.95058-81-4) is a nucleoside analog used as chemotherapy. It can be used in various carcinomas: non-small cell lung cancer, pancreatic cancer, bladder cancer and breast cancer. Gemcitabine is a nucleoside analog used as chemotherapy. Gemcitabine is used in various carcinomas: non-small cell lung cancer, pancreatic cancer, bladder cancer and breast cancer. It is being investigated for use in oesophageal cancer, and is used experimentally in lymphomas and various other tumor types.

Product Name

Gemcitabine

Synthetic route

Gemcitabine Specification

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