CAS No.130288-24-3,Duocarmycin SA Suppliers

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Basic Information

Molecular Structure:
CAS No.:	130288-24-3
Name:	Duocarmycin SA
Article Data:	11

Formula:	C25H23 N3 O7
Molecular Weight:	477.474
Synonyms:	Cyclopropa[c]pyrrolo[3,2-e]indole-6-carboxylicacid,1,2,4,5,8,8a-hexahydro-4-oxo-2-[(5,6,7-trimethoxy-1H-indol-2-yl)carbonyl]-,methyl ester, (7bR)- (9CI); (+)-Duocarmycin SA; Antibiotic DC 113; DuocarmycinSA
Density:	1.53g/cm³
Boiling Point:	787.7°Cat760mmHg
Flash Point:	430.2°C
PSA:	122.95000
LogP:	2.74020

Synthetic route

: methyl (S)-4-hydroxy-8-(hydroxymethyl)-6-(5,6,7-trimethoxy-1Hindole-2-carbonyl)-3,6,7,8-tetrahydropyrrolo[3,2-e]indole-2-carboxylate

: 130288-24-3
(+)-duocarmycin SA

Conditions

Conditions	Yield
With tributylphosphine; azodicarbonyl dimorpholide In tetrahydrofuran for 2h; Inert atmosphere; enantioselective reaction;	94%
With tributylphosphine; 1,1'-azodicarbonyl-dipiperidine In tetrahydrofuran for 0.333333h; Inert atmosphere;

: (8S)-4-hydroxy-8-methanesulfonyloxymethyl-6-(5,6,7-trimethoxy-1H-indole-2-carbonyl)-3,6,7,8-tetrahydro-3,6-diaza-as-indacene-2-carboxylic acid methyl ester

: 130288-24-3
(+)-duocarmycin SA

Conditions

Conditions	Yield
With caesium carbonate In acetonitrile at 23℃; for 1h;	92%

: 144667-38-9
duocarmycin

: 130288-24-3
(+)-duocarmycin SA

Conditions

Conditions	Yield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile for 3h; Ambient temperature;	91%
With sodium hydride In tetrahydrofuran; N,N-dimethyl-formamide at 0℃; for 0.5h;	87%
With sodium hydride In tetrahydrofuran; N,N-dimethyl-formamide at 0℃; for 30h;
With sodium hydrogencarbonate In N,N-dimethyl-formamide at 25℃; for 1h;

: 919535-11-8
methyl (S)-4-[(5,6,7-trimethoxyindol-2yl)carbonyl]-2,6-dihydroxy-1,2,3,4-tetrahydropyrrolo[3,2-f]quinoline-8-carboxylate

: 130288-24-3
(+)-duocarmycin SA

Conditions

Conditions	Yield
With tributylphosphine; 1,1'-azodicarbonyl-dipiperidine In tetrahydrofuran at 25℃; for 0.5h; Mitsunobu reaction;	62%

: (R)-8-Chloromethyl-4-hydroxy-6-(5,6,7-trimethoxy-1H-indole-2-carbonyl)-3,6,7,8-tetrahydro-pyrrolo[3,2-e]indole-2-carboxylic acid methyl ester

: 130288-24-3
(+)-duocarmycin SA

Conditions

Conditions	Yield
With sodium hydride In tetrahydrofuran; N,N-dimethyl-formamide at 0℃; for 30h;

: C13H12N2O3

: 157425-68-8
1-(5,6,7-trimethoxyindole-2-carbonyl)imidazole

: 130288-24-3
(+)-duocarmycin SA

Conditions

Conditions	Yield
With sodium hydride 1.) DMF, THF, 2.) DMF, THF, 0 deg C; Yield given. Multistep reaction;

: 150992-82-8
(+)-(7bR,8aS)-methyl 4-oxo-1,2,4,5,8,8a-hexahydrocyclopropapyrrolo<3,2-e>indole-6-carboxylate

: 157425-68-8
1-(5,6,7-trimethoxyindole-2-carbonyl)imidazole

: 130288-24-3
(+)-duocarmycin SA

Conditions

Conditions	Yield
With sodium hydride 1.) DMF-THF, 2.) 0 deg C; Yield given. Multistep reaction;
With sodium hydride 1.) THF, DMF, 0 deg C, 20 min, 2.) THF, DMF, 0 deg C, 4 h; Yield given. Multistep reaction;

: 151062-83-8
methyl (7bS)-(-)-1,2,4,5,8,8a-hexahydro-4-oxocyclopropapyrrolo<3,2-e>indole-6-carboxylate

: 157425-68-8
1-(5,6,7-trimethoxyindole-2-carbonyl)imidazole

: 130288-24-3
(+)-duocarmycin SA

Conditions

Conditions	Yield
With sodium hydride 1.) THF, DMF, 0 deg C, 20 min, 2.) THF, DMF, 0 deg C, 4 h; Yield given. Multistep reaction;

: 881422-32-8
3-(benzyloxy)-5-nitrobenzaldehyde

A: 130288-24-3
(+)-duocarmycin SA

B calf thymus DNA: calf thymus DNA

Conditions

Conditions	Yield
Multi-step reaction with 12 steps 1.1: 78 percent / NaOMe / methanol; tetrahydrofuran / 17 h / -25 °C 2.1: 68 percent / xylene / 7 h / 140 °C 3.1: 98 percent / DMAP / tetrahydrofuran / 1 h / 25 °C 4.1: 98 percent / Zn; NH4Cl / acetone; H2O / 0.5 h / 25 °C 5.1: 227 mg / tetrahydrofuran / 10 h / 25 °C 6.1: 91 percent / N-iodosuccinimide; AcOH / toluene / 8 h / 25 °C 7.1: 96 percent / NaH / dimethylformamide / 2 h / 0 °C 8.1: i-PrMgBr / tetrahydrofuran / 1 h / -40 °C 8.2: 69 percent / CuI; Bu3P / tetrahydrofuran / 1.5 h / -78 - -40 °C 9.1: 82 percent / H2 / Pd/C / methanol; tetrahydrofuran / 0.5 h / 25 °C 10.1: HCl / ethyl acetate / 3 h / 25 °C 11.1: 3.7 mg / EDCI / dimethylformamide / 2 h / 0 °C 12.1: 62 percent / Bu3P; ADDP / tetrahydrofuran / 0.5 h / 25 °C View Scheme

Yield

Multi-step reaction with 12 steps
1.1: 78 percent / NaOMe / methanol; tetrahydrofuran / 17 h / -25 °C
2.1: 68 percent / xylene / 7 h / 140 °C
3.1: 98 percent / DMAP / tetrahydrofuran / 1 h / 25 °C
4.1: 98 percent / Zn; NH4Cl / acetone; H2O / 0.5 h / 25 °C
5.1: 227 mg / tetrahydrofuran / 10 h / 25 °C
6.1: 91 percent / N-iodosuccinimide; AcOH / toluene / 8 h / 25 °C
7.1: 96 percent / NaH / dimethylformamide / 2 h / 0 °C
8.1: i-PrMgBr / tetrahydrofuran / 1 h / -40 °C
8.2: 69 percent / CuI; Bu3P / tetrahydrofuran / 1.5 h / -78 - -40 °C
9.1: 82 percent / H2 / Pd/C / methanol; tetrahydrofuran / 0.5 h / 25 °C
10.1: HCl / ethyl acetate / 3 h / 25 °C
11.1: 3.7 mg / EDCI / dimethylformamide / 2 h / 0 °C
12.1: 62 percent / Bu3P; ADDP / tetrahydrofuran / 0.5 h / 25 °C
View Scheme

: methyl 2-azido-3-(3-benzyloxy-5-nitrophenyl)acrylate

A: 130288-24-3
(+)-duocarmycin SA

B calf thymus DNA: calf thymus DNA

Conditions

Conditions	Yield
Multi-step reaction with 11 steps 1.1: 68 percent / xylene / 7 h / 140 °C 2.1: 98 percent / DMAP / tetrahydrofuran / 1 h / 25 °C 3.1: 98 percent / Zn; NH4Cl / acetone; H2O / 0.5 h / 25 °C 4.1: 227 mg / tetrahydrofuran / 10 h / 25 °C 5.1: 91 percent / N-iodosuccinimide; AcOH / toluene / 8 h / 25 °C 6.1: 96 percent / NaH / dimethylformamide / 2 h / 0 °C 7.1: i-PrMgBr / tetrahydrofuran / 1 h / -40 °C 7.2: 69 percent / CuI; Bu3P / tetrahydrofuran / 1.5 h / -78 - -40 °C 8.1: 82 percent / H2 / Pd/C / methanol; tetrahydrofuran / 0.5 h / 25 °C 9.1: HCl / ethyl acetate / 3 h / 25 °C 10.1: 3.7 mg / EDCI / dimethylformamide / 2 h / 0 °C 11.1: 62 percent / Bu3P; ADDP / tetrahydrofuran / 0.5 h / 25 °C View Scheme

Yield

Multi-step reaction with 11 steps
1.1: 68 percent / xylene / 7 h / 140 °C
2.1: 98 percent / DMAP / tetrahydrofuran / 1 h / 25 °C
3.1: 98 percent / Zn; NH4Cl / acetone; H2O / 0.5 h / 25 °C
4.1: 227 mg / tetrahydrofuran / 10 h / 25 °C
5.1: 91 percent / N-iodosuccinimide; AcOH / toluene / 8 h / 25 °C
6.1: 96 percent / NaH / dimethylformamide / 2 h / 0 °C
7.1: i-PrMgBr / tetrahydrofuran / 1 h / -40 °C
7.2: 69 percent / CuI; Bu3P / tetrahydrofuran / 1.5 h / -78 - -40 °C
8.1: 82 percent / H2 / Pd/C / methanol; tetrahydrofuran / 0.5 h / 25 °C
9.1: HCl / ethyl acetate / 3 h / 25 °C
10.1: 3.7 mg / EDCI / dimethylformamide / 2 h / 0 °C
11.1: 62 percent / Bu3P; ADDP / tetrahydrofuran / 0.5 h / 25 °C
View Scheme