(S)-10-Hydroxycamptothecin supplier

Name
10-Hydroxycamptothecin
EINECS 805-668-4
CAS No. 19685-09-7
Article Data22
CAS DataBase
Density 1.6 g/cm³
Solubility
Melting Point 265-270 °C
Formula C₂₀H₁₆N₂O₅
Boiling Point 820.7 °C at 760 mmHg
Molecular Weight 364.357
Flash Point 450.1 °C
Transport Information
Appearance Yellow solid
Safety 26-36
Risk Codes 36/37/38
Molecular Structure
Hazard Symbols Xi
Synonyms 10-Hydroxy-CPT;Camptothecin, hydroxy-;1H-Pyrano(3,4:6,7)indolizino(1,2-b)quinoline-3,14(4H,12H)-dione, 4-ethyl-4,9-dihydroxy-, hydrate, (S)-;(4S)-4-Ethyl-4,9-dihydroxy-1H-pyrano[3,4:6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione;Camptothecine, 10-hydroxy- (8CI);Hydroxycamptothecine;1H-Pyrano(3,4:6,7)indolizino(1,2-b)quinoline-3,14(4H,12H)-dione-,4-ethyl-4,9-dihydroxy-, (S)- (9CI);
PSA 101.65000
LogP 1.78520

Synthetic route

: 7689-03-4
camptothecin

: 19685-09-7
(S)-10-hydroxycamptothecin

Conditions

Conditions	Yield
Stage #1: camptothecin With hydrogen; acetic acid; platinum(IV) oxide Stage #2: With lead(IV) acetate; acetic acid	51%
Yield given. Multistep reaction;
With sulfuric acid; dihydrogen peroxide; acetic acid 2) irradiation; Yield given. Multistep reaction;

: 19685-10-0
10-methoxycamptothecin

: 19685-09-7
(S)-10-hydroxycamptothecin

Conditions

Conditions	Yield
With hydrogen bromide at 110℃; for 72h;	82%
With hydrogen bromide In water at 110℃; for 7h; Inert atmosphere; optical yield given as %ee;	80%
With hydrogen bromide In water at 100℃; Sealed tube;	80%
With hydrogen bromide	72%
With hydrogen bromide In water for 2h; Reflux;

: 7689-03-4
camptothecin

A: 19685-09-7
(S)-10-hydroxycamptothecin

B: 19685-11-1
(S)-9-acetoxy-4-ethyl-4-hydroxy-1,12-dihydro-4H-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14-dione

Conditions

Conditions	Yield
Stage #1: camptothecin With hydrogen; acetic acid; platinum under 760.051 Torr; for 8.5h; Stage #2: With lead(IV) acetate In acetic acid Heating / reflux;

: 870527-52-9
1,2,6,7-tetrahydro-(20S)-camphthotecine

: 19685-09-7
(S)-10-hydroxycamptothecin

Conditions

Conditions	Yield
With [bis(acetoxy)iodo]benzene; water In acetic acid Yield given;
With [bis(acetoxy)iodo]benzene; acetic acid
In acetic acid at 20℃;
With [bis(acetoxy)iodo]benzene; acetic acid In water at 20℃; for 18h; Large scale reaction;	1.36 kg

: tetrahydrocamptothecin acetate

: 19685-09-7
(S)-10-hydroxycamptothecin

Conditions

Conditions	Yield
Stage #1: tetrahydrocamptothecin acetate With [bis(acetoxy)iodo]benzene In water; acetic acid at 27.5℃; for 18h; Stage #2: With methanol In N,N-dimethyl-formamide at 27.5 - 76.5℃; for 6h;

10-hydroxycamptothecin: 10-hydroxycamptothecin

: 19685-09-7
(S)-10-hydroxycamptothecin

Conditions

Conditions	Yield
In 1,4-dioxane; acetonitrile for 0.75h; UV-irradiation;	98.5%

9-<(dimethylamino)methyl>-10-hydroxy-(20S)-camptothecin acetate salt: 123948-88-9
9-<(dimethylamino)methyl>-10-hydroxy-(20S)-camptothecin acetate salt

A: 942429-91-6
(S)-10-[(dimethylamino)methyl]-4-ethyl-4,9-dihydroxy-12-methylene-1,12-dihydro-4H-2-oxa-6,12a-diaza-dibenzo[b,h]fluorene-3,13-dione

B: 19685-09-7
(S)-10-hydroxycamptothecin

C: 119413-54-6, 123949-07-5
Topotecan hydrochloride

D: 7689-03-4
camptothecin

Conditions

Conditions	Yield
With hydrogenchloride In water for 0.25h;	A < 0.04 %Chromat. B < 0.001 %Chromat. C 99.65 %Chromat. D < 0.009 %Chromat.

...Expand

: 53544-22-2, 142696-57-9, 142696-58-0
1,2,6,7-tetrahydrocamptothecin

: 19685-09-7
(S)-10-hydroxycamptothecin

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1: 98 percent / pyridine / 1 h / 70 °C 2: 96.3 percent / H2SO4, conc. aq. HNO3 / 1 h 3: 82.3 percent / 20percent aq. H2SO4 / 2 h / Heating 4: 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) / dioxane / 2 h / Heating 5: 96.2 percent / H2 / PtO2 / ethanol; dioxane / 2 h / 760 Torr 6: 1.) 20percent aq. H2SO4, aq. NaNO2, 2.) H2O / 1.) 0-5 deg C, 15 min, 2.) reflux, 1 h View Scheme
Multi-step reaction with 3 steps 1: 12 percent / Pb(OAc)4, trifluoroacetic acid / 0.25 h / Ambient temperature 2: 90.6 percent / 30percent aq. H2O2, acetic acid / 3.5 h / 70 - 80 °C 3: 22.5 percent / 1 N H2SO4 / dioxane / 0.5 h / Irradiation View Scheme
Multi-step reaction with 3 steps 1: 12 percent / Pb(OAc)4, trifluoroacetic acid / 0.25 h / Ambient temperature 2: 90.6 percent / 30percent aq. H2O2, acetic acid / 3.5 h / 70 - 80 °C 3: 25 percent / 1 N aq. H2SO4 / dioxane / 0.5 h / Irradiation View Scheme
Multi-step reaction with 3 steps 1: 12 percent / Pb(OAc)4, trifluoroacetic acid / 0.25 h / Ambient temperature 2: 90.6 percent / 30percent aq. H2O2, acetic acid / 3.5 h / 70 - 80 °C 3: 58 percent / 1 N aq. H2SO4 / dioxane / 0.5 h / Irradiation View Scheme

: 161681-84-1
2-[2,2-Dimethoxy-eth-(Z)-ylidene]-malonic acid benzyl ester methyl ester

: 19685-09-7
(S)-10-hydroxycamptothecin

Conditions

Conditions	Yield
Multi-step reaction with 8 steps 1: LDA / tetrahydrofuran / -78 up to -20 deg C 2: H2 / 5percent Pd/C / methanol 3: 89 percent / 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide, 1-hydroxybenzotriazole (HOBT), Et3N / tetrahydrofuran 4: TFA / H2O; toluene 5: DDQ 6: diisobutylaluminum hydride (DIBAH) / CH2Cl2 7: 1.) NaBH4; 2.) aq. NaOH / 1.) MeOH 8: 72 percent / 48percent HBr View Scheme
Multi-step reaction with 8 steps 1: LDA / tetrahydrofuran / -78 up to -20 deg C 2: H2 / 5percent Pd/C / methanol 3: 89 percent / 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide, 1-hydroxybenzotriazole (HOBT), Et3N / tetrahydrofuran 4: TFA / H2O; toluene 5: DDQ 6: diisobutylaluminum hydride (DIBAH) / CH2Cl2 7: NaBH4 / methanol 8: 72 percent / 48percent HBr View Scheme

: 2-[1-((2R,4S)-2-tert-Butyl-4-ethyl-5-oxo-[1,3]dioxolan-4-yl)-2,2-dimethoxy-ethyl]-malonic acid benzyl ester methyl ester

: 19685-09-7
(S)-10-hydroxycamptothecin

Conditions

Conditions	Yield
Multi-step reaction with 7 steps 1: H2 / 5percent Pd/C / methanol 2: 89 percent / 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide, 1-hydroxybenzotriazole (HOBT), Et3N / tetrahydrofuran 3: TFA / H2O; toluene 4: DDQ 5: diisobutylaluminum hydride (DIBAH) / CH2Cl2 6: 1.) NaBH4; 2.) aq. NaOH / 1.) MeOH 7: 72 percent / 48percent HBr View Scheme
Multi-step reaction with 7 steps 1: H2 / 5percent Pd/C / methanol 2: 89 percent / 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide, 1-hydroxybenzotriazole (HOBT), Et3N / tetrahydrofuran 3: TFA / H2O; toluene 4: DDQ 5: diisobutylaluminum hydride (DIBAH) / CH2Cl2 6: NaBH4 / methanol 7: 72 percent / 48percent HBr View Scheme

: 173442-34-7
(S)-4-ethyl-4-hydroxy-6-iodo-3-oxo-1H-pyrano[3,4-c]-8-pyridone

: 19685-09-7
(S)-10-hydroxycamptothecin

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 78 percent / NaH, LiBr / 1,2-dimethoxy-ethane; dimethylformamide / 1.) 0 deg C, 10 min; r.t., 15 min, 2.) toluene, 70 deg C, 20 h 2: 51 percent / Me6Sn2 / benzene / 5 h / 70 °C / Irradiation 3: 82 percent / aq. HBr / 72 h / 110 °C View Scheme
Multi-step reaction with 2 steps 1: 88 percent / NaH, LiBr / 1,2-dimethoxy-ethane; dimethylformamide 2: Me3SnSnMe3 / benzene / 70 °C / Irradiation View Scheme

: 174092-79-6
(S)-4-ethyl-4-hydroxy-6-iodo-8-methoxy-1,4-dihydro-pyrano[3,4-c]pyridin-3-one

: 19685-09-7
(S)-10-hydroxycamptothecin

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: 73 percent / Me3SiCl, NaI / acetonitrile; H2O / 5 h / 65 °C 2: 78 percent / NaH, LiBr / 1,2-dimethoxy-ethane; dimethylformamide / 1.) 0 deg C, 10 min; r.t., 15 min, 2.) toluene, 70 deg C, 20 h 3: 51 percent / Me6Sn2 / benzene / 5 h / 70 °C / Irradiation 4: 82 percent / aq. HBr / 72 h / 110 °C View Scheme
Multi-step reaction with 3 steps 1: 72 percent / aq. HI 2: 88 percent / NaH, LiBr / 1,2-dimethoxy-ethane; dimethylformamide 3: Me3SnSnMe3 / benzene / 70 °C / Irradiation View Scheme

: 86639-48-7
Camptothecin 1-oxide

: 19685-09-7
(S)-10-hydroxycamptothecin

Conditions

Conditions	Yield
Multi-step reaction with 8 steps 1: 11.5 percent / 1 N aq. H2SO4 / dioxane / 0.5 h / Irradiation 2: H2, acetic acid / PtO2 / dioxane / 760 Torr 3: 98 percent / pyridine / 1 h / 70 °C 4: 96.3 percent / H2SO4, conc. aq. HNO3 / 1 h 5: 82.3 percent / 20percent aq. H2SO4 / 2 h / Heating 6: 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) / dioxane / 2 h / Heating 7: 96.2 percent / H2 / PtO2 / ethanol; dioxane / 2 h / 760 Torr 8: 1.) 20percent aq. H2SO4, aq. NaNO2, 2.) H2O / 1.) 0-5 deg C, 15 min, 2.) reflux, 1 h View Scheme
Multi-step reaction with 3 steps 1: 11.5 percent / 1 N aq. H2SO4 / dioxane / 0.5 h / Irradiation 2: H2, acetic acid / PtO2 / dioxane / 760 Torr 3: 73.5 percent / Pb(OAc)4, trifluoroacetic acid / 0.25 h / Ambient temperature View Scheme

Yield

Multi-step reaction with 8 steps
1: 11.5 percent / 1 N aq. H2SO4 / dioxane / 0.5 h / Irradiation
2: H2, acetic acid / PtO2 / dioxane / 760 Torr
3: 98 percent / pyridine / 1 h / 70 °C
4: 96.3 percent / H2SO4, conc. aq. HNO3 / 1 h
5: 82.3 percent / 20percent aq. H2SO4 / 2 h / Heating
6: 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) / dioxane / 2 h / Heating
7: 96.2 percent / H2 / PtO2 / ethanol; dioxane / 2 h / 760 Torr
8: 1.) 20percent aq. H2SO4, aq. NaNO2, 2.) H2O / 1.) 0-5 deg C, 15 min, 2.) reflux, 1 h
View Scheme

Multi-step reaction with 3 steps
1: 11.5 percent / 1 N aq. H2SO4 / dioxane / 0.5 h / Irradiation
2: H2, acetic acid / PtO2 / dioxane / 760 Torr
3: 73.5 percent / Pb(OAc)4, trifluoroacetic acid / 0.25 h / Ambient temperature
View Scheme

: 86639-48-7
Camptothecin 1-oxide

A: 19685-09-7
(S)-10-hydroxycamptothecin

B: 86639-49-8
((S)-4-Ethyl-4-hydroxy-3,13-dioxo-3,4,12,13-tetrahydro-1H-2-oxa-6,12a-diaza-dibenzo[b,h]fluoren-9-ylsulfanyl)-acetic acid ethyl ester

Conditions

Conditions	Yield
With sulfuric acid In 1,4-dioxane for 0.5h; Irradiation;	A 58% B 11.9%

...Expand

: 86639-62-5
10-nitro-(20S)-camptothecin

: 19685-09-7
(S)-10-hydroxycamptothecin

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 96.2 percent / H2 / PtO2 / ethanol; dioxane / 2 h / 760 Torr 2: 1.) 20percent aq. H2SO4, aq. NaNO2, 2.) H2O / 1.) 0-5 deg C, 15 min, 2.) reflux, 1 h View Scheme

N,20-O-diacetyl-1,2,6,7-tetrahydrocamptothecin: N,20-O-diacetyl-1,2,6,7-tetrahydrocamptothecin

: 19685-09-7
(S)-10-hydroxycamptothecin

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: 96.3 percent / H2SO4, conc. aq. HNO3 / 1 h 2: 82.3 percent / 20percent aq. H2SO4 / 2 h / Heating 3: 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) / dioxane / 2 h / Heating 4: 96.2 percent / H2 / PtO2 / ethanol; dioxane / 2 h / 760 Torr 5: 1.) 20percent aq. H2SO4, aq. NaNO2, 2.) H2O / 1.) 0-5 deg C, 15 min, 2.) reflux, 1 h View Scheme

: Acetic acid (4R,5bS,11aS)-4-acetoxy-4-ethyl-9-nitro-3,13-dioxo-3,4,5b,11a,12,13-hexahydro-1H,11H-2-oxa-6,12a-diaza-dibenzo[b,h]fluoren-6-yl ester

: 19685-09-7
(S)-10-hydroxycamptothecin

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: 82.3 percent / 20percent aq. H2SO4 / 2 h / Heating 2: 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) / dioxane / 2 h / Heating 3: 96.2 percent / H2 / PtO2 / ethanol; dioxane / 2 h / 760 Torr 4: 1.) 20percent aq. H2SO4, aq. NaNO2, 2.) H2O / 1.) 0-5 deg C, 15 min, 2.) reflux, 1 h View Scheme

: 174092-80-9
(S)-4-ethyl-4-hydroxy-6-iodo-7-(prop-2-yn-1-yl)-1,7-dihydro-3H-pyrano[3,4-c]pyridino-3,8(4H)-dione

: 19685-09-7
(S)-10-hydroxycamptothecin

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 51 percent / Me6Sn2 / benzene / 5 h / 70 °C / Irradiation 2: 82 percent / aq. HBr / 72 h / 110 °C View Scheme

: 19685-09-7
(S)-10-hydroxycamptothecin

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: 45 percent / ICl / CCl4; CH2Cl2 / 48 h / Ambient temperature 2: 73 percent / Me3SiCl, NaI / acetonitrile; H2O / 5 h / 65 °C 3: 78 percent / NaH, LiBr / 1,2-dimethoxy-ethane; dimethylformamide / 1.) 0 deg C, 10 min; r.t., 15 min, 2.) toluene, 70 deg C, 20 h 4: 51 percent / Me6Sn2 / benzene / 5 h / 70 °C / Irradiation 5: 82 percent / aq. HBr / 72 h / 110 °C View Scheme

Yield

Multi-step reaction with 5 steps
1: 45 percent / ICl / CCl4; CH2Cl2 / 48 h / Ambient temperature
2: 73 percent / Me3SiCl, NaI / acetonitrile; H2O / 5 h / 65 °C
3: 78 percent / NaH, LiBr / 1,2-dimethoxy-ethane; dimethylformamide / 1.) 0 deg C, 10 min; r.t., 15 min, 2.) toluene, 70 deg C, 20 h
4: 51 percent / Me6Sn2 / benzene / 5 h / 70 °C / Irradiation
5: 82 percent / aq. HBr / 72 h / 110 °C
View Scheme

: 170453-55-1
2-methoxy-6-(trimethylsilyl)pyridine

: 19685-09-7
(S)-10-hydroxycamptothecin

Conditions

Conditions	Yield
Multi-step reaction with 9 steps 1: tBuLi 2: nBuLi, I2 3: 63 percent / Et3SiH / trifluoroacetic acid 4: 69 percent / K2CO3, Bu4NBr / Pd(OAc)2 5: 1.) OsO4, (DHQD)2-Pyr, 2.) I2, CaCO3 6: 47 percent / ICl 7: 72 percent / aq. HI 8: 88 percent / NaH, LiBr / 1,2-dimethoxy-ethane; dimethylformamide 9: Me3SnSnMe3 / benzene / 70 °C / Irradiation View Scheme

: 453518-21-3
2-Methoxy-6-trimethylsilanyl-pyridine-3-carbaldehyde

: 19685-09-7
(S)-10-hydroxycamptothecin

Conditions

Conditions	Yield
Multi-step reaction with 8 steps 1: nBuLi, I2 2: 63 percent / Et3SiH / trifluoroacetic acid 3: 69 percent / K2CO3, Bu4NBr / Pd(OAc)2 4: 1.) OsO4, (DHQD)2-Pyr, 2.) I2, CaCO3 5: 47 percent / ICl 6: 72 percent / aq. HI 7: 88 percent / NaH, LiBr / 1,2-dimethoxy-ethane; dimethylformamide 8: Me3SnSnMe3 / benzene / 70 °C / Irradiation View Scheme

: 174092-75-2
4-iodo-2-methoxy-6-trimethylsilanyl-3-pyridinecarboxaldehyde

: 19685-09-7
(S)-10-hydroxycamptothecin

Conditions

Conditions	Yield
Multi-step reaction with 7 steps 1: 63 percent / Et3SiH / trifluoroacetic acid 2: 69 percent / K2CO3, Bu4NBr / Pd(OAc)2 3: 1.) OsO4, (DHQD)2-Pyr, 2.) I2, CaCO3 4: 47 percent / ICl 5: 72 percent / aq. HI 6: 88 percent / NaH, LiBr / 1,2-dimethoxy-ethane; dimethylformamide 7: Me3SnSnMe3 / benzene / 70 °C / Irradiation View Scheme

: 3-[((E)-But-2-enyl)oxymethyl]-4-iodo-2-methoxy-6-trimethylsilanyl-pyridine

: 19685-09-7
(S)-10-hydroxycamptothecin

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1: 69 percent / K2CO3, Bu4NBr / Pd(OAc)2 2: 1.) OsO4, (DHQD)2-Pyr, 2.) I2, CaCO3 3: 47 percent / ICl 4: 72 percent / aq. HI 5: 88 percent / NaH, LiBr / 1,2-dimethoxy-ethane; dimethylformamide 6: Me3SnSnMe3 / benzene / 70 °C / Irradiation View Scheme

: 174092-80-9
(S)-4-ethyl-4-hydroxy-6-iodo-7-(prop-2-yn-1-yl)-1,7-dihydro-3H-pyrano[3,4-c]pyridino-3,8(4H)-dione

: 162471-15-0
4-isocyanophenol

: 19685-09-7
(S)-10-hydroxycamptothecin

Conditions

Conditions	Yield
With hexamethyldistannane In benzene at 70℃; Irradiation;

: 86639-48-7
Camptothecin 1-oxide

: 64-19-7
acetic acid

A: 19685-09-7
(S)-10-hydroxycamptothecin

B: 19685-11-1
(S)-9-acetoxy-4-ethyl-4-hydroxy-1,12-dihydro-4H-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14-dione

Conditions

Conditions	Yield
With sulfuric acid In 1,4-dioxane for 0.5h; Irradiation;	A 25% B 30.5%

...Expand

: 161681-89-6
7-Methoxy-1,3-dihydro-pyrrolo[3,4-b]quinoline-2-carboxylic acid methyl ester

: 19685-09-7
(S)-10-hydroxycamptothecin

Conditions

Conditions	Yield
Multi-step reaction with 7 steps 1: 30percent HBr/HOAc / 12 h / 20 °C 2: 89 percent / 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide, 1-hydroxybenzotriazole (HOBT), Et3N / tetrahydrofuran 3: TFA / H2O; toluene 4: DDQ 5: diisobutylaluminum hydride (DIBAH) / CH2Cl2 6: 1.) NaBH4; 2.) aq. NaOH / 1.) MeOH 7: 72 percent / 48percent HBr View Scheme
Multi-step reaction with 7 steps 1: 30percent HBr/HOAc / 12 h / 20 °C 2: 89 percent / 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide, 1-hydroxybenzotriazole (HOBT), Et3N / tetrahydrofuran 3: TFA / H2O; toluene 4: DDQ 5: diisobutylaluminum hydride (DIBAH) / CH2Cl2 6: NaBH4 / methanol 7: 72 percent / 48percent HBr View Scheme

: 2-(Methoxycarbonyl-prop-2-ynyl-amino)-N-(4-methoxy-phenyl)-acetimidic acid methyl ester

: 19685-09-7
(S)-10-hydroxycamptothecin

Conditions

Conditions	Yield
Multi-step reaction with 8 steps 1: acetonitrile / 50 °C 2: 30percent HBr/HOAc / 12 h / 20 °C 3: 89 percent / 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide, 1-hydroxybenzotriazole (HOBT), Et3N / tetrahydrofuran 4: TFA / H2O; toluene 5: DDQ 6: diisobutylaluminum hydride (DIBAH) / CH2Cl2 7: 1.) NaBH4; 2.) aq. NaOH / 1.) MeOH 8: 72 percent / 48percent HBr View Scheme
Multi-step reaction with 8 steps 1: acetonitrile / 50 °C 2: 30percent HBr/HOAc / 12 h / 20 °C 3: 89 percent / 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide, 1-hydroxybenzotriazole (HOBT), Et3N / tetrahydrofuran 4: TFA / H2O; toluene 5: DDQ 6: diisobutylaluminum hydride (DIBAH) / CH2Cl2 7: NaBH4 / methanol 8: 72 percent / 48percent HBr View Scheme

: 2-[1-((2R,4S)-2-tert-Butyl-4-ethyl-5-oxo-[1,3]dioxolan-4-yl)-2,2-dimethoxy-ethyl]-malonic acid monomethyl ester

: 19685-09-7
(S)-10-hydroxycamptothecin

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1: 89 percent / 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide, 1-hydroxybenzotriazole (HOBT), Et3N / tetrahydrofuran 2: TFA / H2O; toluene 3: DDQ 4: diisobutylaluminum hydride (DIBAH) / CH2Cl2 5: 1.) NaBH4; 2.) aq. NaOH / 1.) MeOH 6: 72 percent / 48percent HBr View Scheme
Multi-step reaction with 6 steps 1: 89 percent / 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide, 1-hydroxybenzotriazole (HOBT), Et3N / tetrahydrofuran 2: TFA / H2O; toluene 3: DDQ 4: diisobutylaluminum hydride (DIBAH) / CH2Cl2 5: NaBH4 / methanol 6: 72 percent / 48percent HBr View Scheme

: 7-Methoxy-2,3-dihydro-1H-pyrrolo[3,4-b]quinoline; hydrobromide

: 19685-09-7
(S)-10-hydroxycamptothecin

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1: 89 percent / 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide, 1-hydroxybenzotriazole (HOBT), Et3N / tetrahydrofuran 2: TFA / H2O; toluene 3: DDQ 4: diisobutylaluminum hydride (DIBAH) / CH2Cl2 5: 1.) NaBH4; 2.) aq. NaOH / 1.) MeOH 6: 72 percent / 48percent HBr View Scheme
Multi-step reaction with 6 steps 1: 89 percent / 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide, 1-hydroxybenzotriazole (HOBT), Et3N / tetrahydrofuran 2: TFA / H2O; toluene 3: DDQ 4: diisobutylaluminum hydride (DIBAH) / CH2Cl2 5: NaBH4 / methanol 6: 72 percent / 48percent HBr View Scheme

: 186581-53-3, 908094-01-9
diazomethane

: 19685-09-7
(S)-10-hydroxycamptothecin

: 19685-10-0
10-methoxycamptothecin

Conditions

Conditions	Yield
In 1,4-dioxane; methanol at 20℃; for 2h;	100%
	88%
In 1,4-dioxane; methanol; diethyl ether for 1h; Ambient temperature;	87.5%

: 19685-09-7
(S)-10-hydroxycamptothecin

: 103816-19-9
4-piperidinopiperidine-1-carbonyl chloride

: 103816-16-6
10-[4-(1-piperidino)-1-piperidino]carbonyloxycamptothecin

Conditions

Conditions	Yield
With pyridine In dichloromethane at 20℃; for 4h;	100%

: 19685-09-7
(S)-10-hydroxycamptothecin

: 1097323-11-9
9-bromo-10-hydroxycamptothecin

Conditions

Conditions	Yield
With N-Bromosuccinimide In N,N-dimethyl-formamide at 0 - 20℃; for 2h;	98%
With N-Bromosuccinimide In N,N-dimethyl-formamide	95%

: 37595-74-7
N,N-phenylbistrifluoromethane-sulfonimide

: 19685-09-7
(S)-10-hydroxycamptothecin

: 123949-09-7
10-hydroxy-(20S)-camptothecin trifluoromethanesulfonate

Conditions

Conditions	Yield
With triethylamine In N,N-dimethyl-formamide at 23 - 50℃; Inert atmosphere;	97%
With triethylamine In N,N-dimethyl-formamide at 23 - 50℃;	97%
With triethylamine In N,N-dimethyl-formamide at 20℃;	96.7%
With triethylamine In N,N-dimethyl-formamide at 50℃; for 3h;
With triethylamine In N,N-dimethyl-formamide at 50℃;

: 19685-09-7
(S)-10-hydroxycamptothecin

: 1256544-04-3
9-iodine-10-hydroxycamptothecin

Conditions

Conditions	Yield
With N-iodo-succinimide In N,N-dimethyl-formamide at 0 - 20℃; for 2h;	97%
With N-iodo-succinimide In N,N-dimethyl-formamide at 0 - 20℃; for 2h;	95%

: 1-chlorocarbonyl-4-piperidinopiperidine hydrochloride

: 19685-09-7
(S)-10-hydroxycamptothecin

: 10-[4-(1-piperidino)-1-piperidino]carbonyloxycamptothecin hydrochloride

Conditions

Conditions	Yield
With potassium carbonate; triethylamine In acetonitrile at 60℃; for 6h;	97%

: 108-55-4
glutaric anhydride,

: 19685-09-7
(S)-10-hydroxycamptothecin

: C25H22N2O8

Conditions

Conditions	Yield
With pyridine at 25℃; for 72h;	97%

: 19685-09-7
(S)-10-hydroxycamptothecin

: 97-72-3
2-Methylpropionic anhydride

: camptothecin 10,20-di-O-isobutyrate

Conditions

Conditions	Yield
sulfuric acid at 20 - 100℃; for 16h;	96%

: 19685-09-7
(S)-10-hydroxycamptothecin

: 10-hydroxy-mappicine ketone

Conditions

Conditions	Yield
In various solvent(s) at 200℃; for 9h;	95%

: 994-30-9
triethylsilyl chloride

: 19685-09-7
(S)-10-hydroxycamptothecin

: 1004265-03-5
20(S)-O-triethylsilylcampothecin

Conditions

Conditions	Yield
Stage #1: (S)-10-hydroxycamptothecin With 1H-imidazole In N,N-dimethyl-formamide for 0.166667h; Inert atmosphere; Stage #2: triethylsilyl chloride With dmap In N,N-dimethyl-formamide	94%
Stage #1: (S)-10-hydroxycamptothecin With 1H-imidazole In N,N-dimethyl-formamide at 20℃; for 0.166667h; Inert atmosphere; Stage #2: triethylsilyl chloride With dmap In N,N-dimethyl-formamide at 20℃; for 60h; Inert atmosphere;	94%
With 1H-imidazole; dmap In N,N-dimethyl-formamide for 24.1667h;	94%

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

: 19685-09-7
(S)-10-hydroxycamptothecin

: 362496-88-6
10-tert-butoxycarbonyloxycamptothecin

Conditions

Conditions	Yield
With pyridine In N,N-dimethyl-formamide at 20℃;	94%
With pyridine In N,N-dimethyl-formamide at 20℃;
With pyridine In N,N-dimethyl-formamide at 20℃;	2.1 g
With pyridine In dichloromethane
In pyridine; N,N-dimethyl-formamide at 20℃; Inert atmosphere;

: 108-55-4
glutaric anhydride,

: 19685-09-7
(S)-10-hydroxycamptothecin

: 1353778-70-7
C25H22N2O8

Conditions

Conditions	Yield
With pyridine at 20℃; for 48h;	94%
With pyridine at 20℃;	59.22%

: 19685-09-7
(S)-10-hydroxycamptothecin

: 7693-46-1
4-Nitrophenyl chloroformate

: 656233-42-0
4-nitrophenyl camptothecin-10-yl carbonate

Conditions

Conditions	Yield
With triethylamine In tetrahydrofuran at 20℃; for 1h; Schlenk technique;	93%
With triethylamine In tetrahydrofuran at 0 - 20℃; for 1h;	93%
With triethylamine at 20℃; for 1h;	91%

: 19685-09-7
(S)-10-hydroxycamptothecin

: 945867-58-3
C39H50N4O12

Conditions

Conditions	Yield
With triethylamine In dichloromethane; N,N-dimethyl-formamide at 20℃; for 2h;	92%

: 19685-09-7
(S)-10-hydroxycamptothecin

Cyclohexanecarboxylic acid: Cyclohexanecarboxylic acid

(S)-4-ethyl-4-hydroxy-3,14-dioxo-3,4,12,14-tetrahydro-1H-pyrano[3’,4’:6,7]indolizino[1,2-b]quinolin-9-yl cyclohexanecarboxylate: (S)-4-ethyl-4-hydroxy-3,14-dioxo-3,4,12,14-tetrahydro-1H-pyrano[3’,4’:6,7]indolizino[1,2-b]quinolin-9-yl cyclohexanecarboxylate

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 20℃;	92%

: 19685-09-7
(S)-10-hydroxycamptothecin

: 119413-54-6, 123949-07-5
Topotecan hydrochloride

Conditions

Conditions	Yield
In propan-1-ol; dichloromethane	91%

: 50-00-0
formaldehyd

: 19685-09-7
(S)-10-hydroxycamptothecin

(S)-1-Pyrrolidin-2-yl-methanol: (S)-1-Pyrrolidin-2-yl-methanol

: 1439356-77-0
10-hydroxyl-9-L-prolinol (+)methylcamptothecin

Conditions

Conditions	Yield
In acetic acid at 40 - 90℃; Mannich Aminomethylation;	90.2%

...Expand

: 67-56-1
methanol

: 19685-09-7
(S)-10-hydroxycamptothecin

: 86639-61-4
7-hydroxymethyl-10-hydroxycamptothecin

Conditions

Conditions	Yield
With sulfuric acid; dihydrogen peroxide; iron(II) sulfate at 20℃; for 96h; hydroxymethylation;	90%

: 118-29-6
2-(hydroxymethyl)-1H-isoindole-1,3(2H)-dione

: 19685-09-7
(S)-10-hydroxycamptothecin

: 1352172-54-3
C29H21N3O7

Conditions

Conditions	Yield
With sulfuric acid at 0 - 20℃; for 12h;	90%

: 4887-42-7
N-hydroxymethyl-3,4,5,6-tetrahydrophthalimide

: 19685-09-7
(S)-10-hydroxycamptothecin

: 1352172-55-4
C29H25N3O7

Conditions

Conditions	Yield
With sulfuric acid at 0 - 20℃; for 12h;	90%

: 19685-09-7
(S)-10-hydroxycamptothecin

: 870-63-3
prenyl bromide

: (S)-4-ethyl-4-hydroxy-9-((3-methylbut-2-en-1-yl)oxy)-1,12-dihydro-14H-pyrano[3’,4’:6,7]indolizino[1,2-b]quinoline-3,14(4H)-dione

Conditions

Conditions	Yield
With potassium carbonate In acetone for 3h; Reflux;	90%

: 19685-09-7
(S)-10-hydroxycamptothecin

: 541-41-3
chloroformic acid ethyl ester

: carbonic acid 4-ethoxycarbonyloxy-4-ethyl-3,13-dioxo-3,4,12,13-tetrahydro-1H-2-oxa-6,12a-diaza-dibenzo[b,h]fluoren-9-yl ester ethyl ester

Conditions

Conditions	Yield
With pyridine In 1,2-dichloro-ethane	89.2%

: 19685-09-7
(S)-10-hydroxycamptothecin

poly(ethylene glycol)-O-glycolic acid ether: poly(ethylene glycol)-O-glycolic acid ether

10-camptothecin-[poly(ethylene glycol)-O-glycolic acid ether] ester, Mw=40000: 10-camptothecin-[poly(ethylene glycol)-O-glycolic acid ether] ester, Mw=40000

Conditions

Conditions	Yield
With pyridine; O-phenyl phosphorodichloridate In chloroform at 20℃; for 18h;	89%

: 945867-57-2
C21H38N2O8

: 19685-09-7
(S)-10-hydroxycamptothecin

: 945867-59-4
C41H54N4O13

Conditions

Conditions	Yield
With triethylamine In dichloromethane; N,N-dimethyl-formamide at 20℃; for 2h;	89%

: 106-31-0
butanoic acid anhydride

: 19685-09-7
(S)-10-hydroxycamptothecin

: camptothecin 10,20-di-O-butyrate

Conditions

Conditions	Yield
sulfuric acid at 20 - 100℃;	89%

: 1,3,6,9,12-pentaoxa-2-thiacyclotetradecane 2,2-dioxide

: 19685-09-7
(S)-10-hydroxycamptothecin

: C28H32N2O9

Conditions

Conditions	Yield
Stage #1: 1,3,6,9,12-pentaoxa-2-thiacyclotetradecane 2,2-dioxide; (S)-10-hydroxycamptothecin With potassium carbonate In N,N-dimethyl-formamide at 40℃; Stage #2: With sulfuric acid In tetrahydrofuran; water for 3h; Reflux;	89%

: 19685-09-7
(S)-10-hydroxycamptothecin

: 106-95-6
allyl bromide

: 185425-24-5
10-allyloxycamptothecin

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 20℃; Inert atmosphere;	88.2%
With potassium carbonate In N,N-dimethyl-formamide

: C10H20O8S

: 19685-09-7
(S)-10-hydroxycamptothecin

: C30H36N2O10

Conditions

Conditions	Yield
Stage #1: C10H20O8S; (S)-10-hydroxycamptothecin With potassium carbonate In N,N-dimethyl-formamide at 40℃; Stage #2: With sulfuric acid In tetrahydrofuran; water for 3h; Reflux;	88%

: C18H36O12S

: 19685-09-7
(S)-10-hydroxycamptothecin

: C38H52N2O14

Conditions

Conditions	Yield
Stage #1: C18H36O12S; (S)-10-hydroxycamptothecin With potassium carbonate In N,N-dimethyl-formamide at 40℃; Stage #2: With sulfuric acid In tetrahydrofuran; water for 3h; Reflux;	88%

(S)-10-Hydroxycamptothecin Chemical Properties

Product Name: 10-Hydroxycamptothecin
Molecular Weight: 364.35144 [g/mol]
Molecular Formula: C₂₀H₁₆N₂O₅
XLogP3-AA: 0.6
H-Bond Donor: 2
H-Bond Acceptor: 6
Index of Refraction: 1.776
Molar Refractivity: 94.97 cm³
Molar Volume: 227 cm³
Surface Tension: 92.4 dyne/cm
Density: 1.6 g/cm³
Flash Point: 450.1 °C
Enthalpy of Vaporization: 125.05 kJ/mol
Boiling Point: 820.7 °C at 760 mmHg
Vapour Pressure: 1.67E-28 mmHg at 25 °C
Appearance: Yellow Solid
Melting Point: 265-270 °C
Classification Code of (S)-10-Hydroxycamptothecin (CAS NO.19685-09-7): Drug / Therapeutic Agent; Mutation data; Natural Product
Product Categories: Alkaloids; INTERMEDIATESOFIRINOTECANHCLTRIHYDRATE; Camptothecin series; Natural Plant Extract; Chiral Reagents; Intermediates & Fine Chemicals; Pharmaceuticals; Natural Anti-cancer Medical Materials and It's Derivatives

(S)-10-Hydroxycamptothecin Uses

(S)-10-Hydroxycamptothecin (CAS NO.19685-09-7) is used in the treatment of cancer. It is used to synthesis 7-Ethyl-10-Hydroxy-CPT,SN-38 .

(S)-10-Hydroxycamptothecin Toxicity Data With Reference

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
mouse	LD50	intraperitoneal	104mg/kg (104mg/kg)		Drugs of the Future. Vol. 7, Pg. 629, 1982.
rat	LD	intravenous	> 10mg/kg (10mg/kg)	KIDNEY, URETER, AND BLADDER: URINE VOLUME INCREASED KIDNEY, URETER, AND BLADDER: HEMATURIA	Cancer Chemotherapy and Pharmacology. Vol. 41, Pg. 257, 1998.

(S)-10-Hydroxycamptothecin Safety Profile

Safety Information of (S)-10-Hydroxycamptothecin (CAS NO.19685-09-7):
Hazard Codes:Xi
Risk Statements:36/37/38
36/37/38:Irritating to eyes, respiratory system and skin
Safety Statements:26-36
26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
36:Wear suitable protective clothing
WGK Germany:3

(S)-10-Hydroxycamptothecin Specification

(S)-10-Hydroxycamptothecin (CAS NO.19685-09-7), its Synonyms are (S)-10-Hydroxycamptothecin hydrate ; 10-Hydroxycamptothecin ; 10-Hydroxycamptothecine ; Camptothecin, 10-hydroxy- ; Camptothecin, hydroxy- ; Hydroxycamptothecin ; Hydroxycamptothecine ; 1H-Pyrano(3',4':6,7)indolizino(1,2-b)quinoline-3,14(4H,12H)-dione, 4-ethyl-4,9-dihydroxy-, hydrate, (S)- ; 1H-Pyrano(3',4':6,7)indolizino(1,2-b)quinoline-3,14(4H,12H)-dione-,4-ethyl-4,9-dihydroxy-, (S)- (9CI) ; Camptothecine, 10-hydroxy- (8CI) .

Product Name

10-Hydroxycamptothecin

Synthetic route

(S)-10-Hydroxycamptothecin Chemical Properties

(S)-10-Hydroxycamptothecin Uses

(S)-10-Hydroxycamptothecin Toxicity Data With Reference

(S)-10-Hydroxycamptothecin Safety Profile

(S)-10-Hydroxycamptothecin Specification

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