Product Name

  • Name

    ecteinascidin 743

  • EINECS
  • CAS No. 114899-77-3
  • Article Data16
  • CAS DataBase
  • Density 1.53g/cm3
  • Solubility
  • Melting Point
  • Formula C39H43N3O11S
  • Boiling Point
  • Molecular Weight 761.85
  • Flash Point
  • Transport Information
  • Appearance
  • Safety
  • Risk Codes
  • Molecular Structure Molecular Structure of 114899-77-3 (ecteinascidin 743)
  • Hazard Symbols
  • Synonyms Spiro[6,16-(epithiopropanoxymethano)-7,13-imino-12H-1,3-dioxolo[7,8]isoquino[3,2-b][3]benzazocine-20,1'(2'H)-isoquinolin]-19-one,5-(acetyloxy)-3',4',6,6a,7,13,14,16-octahydro-6',8,14-trihydroxy-7',9-dimethoxy-4,10,23-trimethyl-,[6R-(6a,6ab,7b,13b,14b,16a,20R*)]-;Ecteinascidin 743;Ecteinascidine 743;Et 743;NSC 648766;Trabectedin;Yondelis;
  • PSA 194.02000
  • LogP 3.61780

Synthetic route

(1'R,6R,6aR,7R,13S,14R,16R)-5-(acetyloxy)-3',4',6,6a,7,13,14,16-octahydro-6',8-dihydroxy-7',9-dimethoxy-4,10,23-trimethyl-19-oxo-spiro[6,16-(epithiopropanoxymethano)-7,13-imino-12H-1,3-dioxolo[7,8]isoquino[3,2-b][3]benzazocine-20,1'(2'H)-isoquinoline]-14-carbonitrile
114899-80-8

(1'R,6R,6aR,7R,13S,14R,16R)-5-(acetyloxy)-3',4',6,6a,7,13,14,16-octahydro-6',8-dihydroxy-7',9-dimethoxy-4,10,23-trimethyl-19-oxo-spiro[6,16-(epithiopropanoxymethano)-7,13-imino-12H-1,3-dioxolo[7,8]isoquino[3,2-b][3]benzazocine-20,1'(2'H)-isoquinoline]-14-carbonitrile

ecteinascidin 743
114899-77-3

ecteinascidin 743

Conditions
ConditionsYield
With silver nitrate In water; acetonitrile at 20℃; for 11h;96.9%
With silver nitrate In water; acetonitrile at 20℃; for 24h; Inert atmosphere;95%
With water; copper(l) chloride In tetrahydrofuran at 23℃; for 24h; Inert atmosphere; Darkness;94%
5-(2-amino-ethyl)-2-methoxy-phenol
3213-30-7

5-(2-amino-ethyl)-2-methoxy-phenol

C36H39Cl3N4O11S

C36H39Cl3N4O11S

ecteinascidin 743
114899-77-3

ecteinascidin 743

Conditions
ConditionsYield
Multistep reaction.;
ethyl 2-bromo-2-(6-(methoxymethoxy)-7-methylbenzo[d][1,3]dioxol-4-yl)acetate
874758-51-7

ethyl 2-bromo-2-(6-(methoxymethoxy)-7-methylbenzo[d][1,3]dioxol-4-yl)acetate

ecteinascidin 743
114899-77-3

ecteinascidin 743

Conditions
ConditionsYield
Multi-step reaction with 20 steps
1.1: 68 percent / triethylamine / acetonitrile / 14 h / 0 °C
2.1: 97 percent / imidazole / dimethylformamide / 3 h / 23 °C
3.1: 94 percent / K2CO3; MeOH / 2 h / 23 °C
4.1: Dess-Martin periodinane / CH2Cl2 / 0.33 h / 23 °C
5.1: 1.26 g / ZnCl2 / CH2Cl2; tetrahydrofuran / 0.17 h / 23 °C
6.1: 80 percent / LiBH4 / tetrahydrofuran; methanol / 10 h / 0 °C
7.1: 92 percent / pyridine; DMAP / CH2Cl2 / 0.5 h / 23 °C
8.1: 91 percent / aq. HF / acetonitrile / 2 h / 23 °C
9.1: 93 percent / Dess-Martin periodinane / CH2Cl2 / 0.33 h / 20 °C
10.1: 95 percent / CF3COOH / CH2Cl2 / 0.5 h / 23 °C
11.1: 96 percent / K2CO3; MeOH / 1 h / 20 °C
12.1: 95 percent / DMAP; EDCl / CH2Cl2 / 1 h / 20 °C
13.1: CF3COOH / 2,2,2-trifluoro-ethanol / 3 h / 20 °C
14.1: 143 mg / pyridine; DMAP / CH2Cl2 / 0.5 h / 23 °C
15.1: 87 percent / n-Bu3SnH; AcOH; Pd(PPh3)2Cl2 / CH2Cl2 / 0.33 h / 20 °C
16.1: 97 percent / NaBH3CN; AcOH / acetonitrile; methanol / 2 h / 23 °C
17.1: 92 percent / Zn; AcOH / diethyl ether / 1 h / 23 °C
18.1: 4-formyl-1-methylpyridinium benzenesulfonate / CH2Cl2; dimethylformamide / 0.17 h / 23 °C
18.2: DBU / CH2Cl2; dimethylformamide / 0.25 h / 23 °C
18.3: 53 percent / aq. oxalic acid / CH2Cl2; dimethylformamide / 0.5 h / 23 °C
19.1: 97 percent / NaOAc / ethanol / 3 h / 23 °C
20.1: 92 percent / aq. AgNO3 / acetonitrile / 19 h / 23 °C
View Scheme
ethyl 2-hydroxy-2-(6-(methoxymethoxy)-7-methylbenzo[d][1,3]dioxol-4-yl)acetate
874758-55-1

ethyl 2-hydroxy-2-(6-(methoxymethoxy)-7-methylbenzo[d][1,3]dioxol-4-yl)acetate

ecteinascidin 743
114899-77-3

ecteinascidin 743

Conditions
ConditionsYield
Multi-step reaction with 21 steps
1.1: 91 percent / benzotriazole; thionyl bromide / CH2Cl2 / 0.33 h / 20 °C
2.1: 68 percent / triethylamine / acetonitrile / 14 h / 0 °C
3.1: 97 percent / imidazole / dimethylformamide / 3 h / 23 °C
4.1: 94 percent / K2CO3; MeOH / 2 h / 23 °C
5.1: Dess-Martin periodinane / CH2Cl2 / 0.33 h / 23 °C
6.1: 1.26 g / ZnCl2 / CH2Cl2; tetrahydrofuran / 0.17 h / 23 °C
7.1: 80 percent / LiBH4 / tetrahydrofuran; methanol / 10 h / 0 °C
8.1: 92 percent / pyridine; DMAP / CH2Cl2 / 0.5 h / 23 °C
9.1: 91 percent / aq. HF / acetonitrile / 2 h / 23 °C
10.1: 93 percent / Dess-Martin periodinane / CH2Cl2 / 0.33 h / 20 °C
11.1: 95 percent / CF3COOH / CH2Cl2 / 0.5 h / 23 °C
12.1: 96 percent / K2CO3; MeOH / 1 h / 20 °C
13.1: 95 percent / DMAP; EDCl / CH2Cl2 / 1 h / 20 °C
14.1: CF3COOH / 2,2,2-trifluoro-ethanol / 3 h / 20 °C
15.1: 143 mg / pyridine; DMAP / CH2Cl2 / 0.5 h / 23 °C
16.1: 87 percent / n-Bu3SnH; AcOH; Pd(PPh3)2Cl2 / CH2Cl2 / 0.33 h / 20 °C
17.1: 97 percent / NaBH3CN; AcOH / acetonitrile; methanol / 2 h / 23 °C
18.1: 92 percent / Zn; AcOH / diethyl ether / 1 h / 23 °C
19.1: 4-formyl-1-methylpyridinium benzenesulfonate / CH2Cl2; dimethylformamide / 0.17 h / 23 °C
19.2: DBU / CH2Cl2; dimethylformamide / 0.25 h / 23 °C
19.3: 53 percent / aq. oxalic acid / CH2Cl2; dimethylformamide / 0.5 h / 23 °C
20.1: 97 percent / NaOAc / ethanol / 3 h / 23 °C
21.1: 92 percent / aq. AgNO3 / acetonitrile / 19 h / 23 °C
View Scheme
hydroxy-(7-hydroxy-6-methoxymethoxy-benzo[1,3]dioxol-4-yl)-acetic acid ethyl ester
874758-53-9

hydroxy-(7-hydroxy-6-methoxymethoxy-benzo[1,3]dioxol-4-yl)-acetic acid ethyl ester

ecteinascidin 743
114899-77-3

ecteinascidin 743

Conditions
ConditionsYield
Multi-step reaction with 23 steps
1.1: 95 percent / K2CO3 / dimethylformamide / 1 h / 23 °C
2.1: 93 percent / K3PO4; Pd(PPh3)4 / dioxane / 4 h / 100 °C
3.1: 91 percent / benzotriazole; thionyl bromide / CH2Cl2 / 0.33 h / 20 °C
4.1: 68 percent / triethylamine / acetonitrile / 14 h / 0 °C
5.1: 97 percent / imidazole / dimethylformamide / 3 h / 23 °C
6.1: 94 percent / K2CO3; MeOH / 2 h / 23 °C
7.1: Dess-Martin periodinane / CH2Cl2 / 0.33 h / 23 °C
8.1: 1.26 g / ZnCl2 / CH2Cl2; tetrahydrofuran / 0.17 h / 23 °C
9.1: 80 percent / LiBH4 / tetrahydrofuran; methanol / 10 h / 0 °C
10.1: 92 percent / pyridine; DMAP / CH2Cl2 / 0.5 h / 23 °C
11.1: 91 percent / aq. HF / acetonitrile / 2 h / 23 °C
12.1: 93 percent / Dess-Martin periodinane / CH2Cl2 / 0.33 h / 20 °C
13.1: 95 percent / CF3COOH / CH2Cl2 / 0.5 h / 23 °C
14.1: 96 percent / K2CO3; MeOH / 1 h / 20 °C
15.1: 95 percent / DMAP; EDCl / CH2Cl2 / 1 h / 20 °C
16.1: CF3COOH / 2,2,2-trifluoro-ethanol / 3 h / 20 °C
17.1: 143 mg / pyridine; DMAP / CH2Cl2 / 0.5 h / 23 °C
18.1: 87 percent / n-Bu3SnH; AcOH; Pd(PPh3)2Cl2 / CH2Cl2 / 0.33 h / 20 °C
19.1: 97 percent / NaBH3CN; AcOH / acetonitrile; methanol / 2 h / 23 °C
20.1: 92 percent / Zn; AcOH / diethyl ether / 1 h / 23 °C
21.1: 4-formyl-1-methylpyridinium benzenesulfonate / CH2Cl2; dimethylformamide / 0.17 h / 23 °C
21.2: DBU / CH2Cl2; dimethylformamide / 0.25 h / 23 °C
21.3: 53 percent / aq. oxalic acid / CH2Cl2; dimethylformamide / 0.5 h / 23 °C
22.1: 97 percent / NaOAc / ethanol / 3 h / 23 °C
23.1: 92 percent / aq. AgNO3 / acetonitrile / 19 h / 23 °C
View Scheme
hydroxy-(6-methoxymethoxy-7-trifluoromethanesulfonyloxy-benzo[1,3]dioxol-4-yl)-acetic acid ethyl ester
874758-54-0

hydroxy-(6-methoxymethoxy-7-trifluoromethanesulfonyloxy-benzo[1,3]dioxol-4-yl)-acetic acid ethyl ester

ecteinascidin 743
114899-77-3

ecteinascidin 743

Conditions
ConditionsYield
Multi-step reaction with 22 steps
1.1: 93 percent / K3PO4; Pd(PPh3)4 / dioxane / 4 h / 100 °C
2.1: 91 percent / benzotriazole; thionyl bromide / CH2Cl2 / 0.33 h / 20 °C
3.1: 68 percent / triethylamine / acetonitrile / 14 h / 0 °C
4.1: 97 percent / imidazole / dimethylformamide / 3 h / 23 °C
5.1: 94 percent / K2CO3; MeOH / 2 h / 23 °C
6.1: Dess-Martin periodinane / CH2Cl2 / 0.33 h / 23 °C
7.1: 1.26 g / ZnCl2 / CH2Cl2; tetrahydrofuran / 0.17 h / 23 °C
8.1: 80 percent / LiBH4 / tetrahydrofuran; methanol / 10 h / 0 °C
9.1: 92 percent / pyridine; DMAP / CH2Cl2 / 0.5 h / 23 °C
10.1: 91 percent / aq. HF / acetonitrile / 2 h / 23 °C
11.1: 93 percent / Dess-Martin periodinane / CH2Cl2 / 0.33 h / 20 °C
12.1: 95 percent / CF3COOH / CH2Cl2 / 0.5 h / 23 °C
13.1: 96 percent / K2CO3; MeOH / 1 h / 20 °C
14.1: 95 percent / DMAP; EDCl / CH2Cl2 / 1 h / 20 °C
15.1: CF3COOH / 2,2,2-trifluoro-ethanol / 3 h / 20 °C
16.1: 143 mg / pyridine; DMAP / CH2Cl2 / 0.5 h / 23 °C
17.1: 87 percent / n-Bu3SnH; AcOH; Pd(PPh3)2Cl2 / CH2Cl2 / 0.33 h / 20 °C
18.1: 97 percent / NaBH3CN; AcOH / acetonitrile; methanol / 2 h / 23 °C
19.1: 92 percent / Zn; AcOH / diethyl ether / 1 h / 23 °C
20.1: 4-formyl-1-methylpyridinium benzenesulfonate / CH2Cl2; dimethylformamide / 0.17 h / 23 °C
20.2: DBU / CH2Cl2; dimethylformamide / 0.25 h / 23 °C
20.3: 53 percent / aq. oxalic acid / CH2Cl2; dimethylformamide / 0.5 h / 23 °C
21.1: 97 percent / NaOAc / ethanol / 3 h / 23 °C
22.1: 92 percent / aq. AgNO3 / acetonitrile / 19 h / 23 °C
View Scheme
(R)-4-((1R,3S)-8-Hydroxy-3-hydroxymethyl-7-methoxy-6-methyl-1,2,3,4-tetrahydro-isoquinolin-1-yl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester
874758-56-2

(R)-4-((1R,3S)-8-Hydroxy-3-hydroxymethyl-7-methoxy-6-methyl-1,2,3,4-tetrahydro-isoquinolin-1-yl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

ecteinascidin 743
114899-77-3

ecteinascidin 743

Conditions
ConditionsYield
Multi-step reaction with 24 steps
1.1: 88 percent / aq. NaHCO3 / CH2Cl2 / 2 h / 20 °C
2.1: 86 percent / Cs2CO3; CsI / dimethylformamide / 3 h / 20 °C
3.1: 92 percent / pyridine; DMAP / CH2Cl2 / 1 h / 20 °C
4.1: 72 percent / trfifluoroacetic acid / CH2Cl2 / 4 h / 20 °C
5.1: 68 percent / triethylamine / acetonitrile / 14 h / 0 °C
6.1: 97 percent / imidazole / dimethylformamide / 3 h / 23 °C
7.1: 94 percent / K2CO3; MeOH / 2 h / 23 °C
8.1: Dess-Martin periodinane / CH2Cl2 / 0.33 h / 23 °C
9.1: 1.26 g / ZnCl2 / CH2Cl2; tetrahydrofuran / 0.17 h / 23 °C
10.1: 80 percent / LiBH4 / tetrahydrofuran; methanol / 10 h / 0 °C
11.1: 92 percent / pyridine; DMAP / CH2Cl2 / 0.5 h / 23 °C
12.1: 91 percent / aq. HF / acetonitrile / 2 h / 23 °C
13.1: 93 percent / Dess-Martin periodinane / CH2Cl2 / 0.33 h / 20 °C
14.1: 95 percent / CF3COOH / CH2Cl2 / 0.5 h / 23 °C
15.1: 96 percent / K2CO3; MeOH / 1 h / 20 °C
16.1: 95 percent / DMAP; EDCl / CH2Cl2 / 1 h / 20 °C
17.1: CF3COOH / 2,2,2-trifluoro-ethanol / 3 h / 20 °C
18.1: 143 mg / pyridine; DMAP / CH2Cl2 / 0.5 h / 23 °C
19.1: 87 percent / n-Bu3SnH; AcOH; Pd(PPh3)2Cl2 / CH2Cl2 / 0.33 h / 20 °C
20.1: 97 percent / NaBH3CN; AcOH / acetonitrile; methanol / 2 h / 23 °C
21.1: 92 percent / Zn; AcOH / diethyl ether / 1 h / 23 °C
22.1: 4-formyl-1-methylpyridinium benzenesulfonate / CH2Cl2; dimethylformamide / 0.17 h / 23 °C
22.2: DBU / CH2Cl2; dimethylformamide / 0.25 h / 23 °C
22.3: 53 percent / aq. oxalic acid / CH2Cl2; dimethylformamide / 0.5 h / 23 °C
23.1: 97 percent / NaOAc / ethanol / 3 h / 23 °C
24.1: 92 percent / aq. AgNO3 / acetonitrile / 19 h / 23 °C
View Scheme
(1R,3S)-3-Acetoxymethyl-8-allyloxy-1-((R)-1-amino-2-hydroxy-ethyl)-7-methoxy-6-methyl-3,4-dihydro-1H-isoquinoline-2-carboxylic acid allyl ester
874758-59-5

(1R,3S)-3-Acetoxymethyl-8-allyloxy-1-((R)-1-amino-2-hydroxy-ethyl)-7-methoxy-6-methyl-3,4-dihydro-1H-isoquinoline-2-carboxylic acid allyl ester

ecteinascidin 743
114899-77-3

ecteinascidin 743

Conditions
ConditionsYield
Multi-step reaction with 20 steps
1.1: 68 percent / triethylamine / acetonitrile / 14 h / 0 °C
2.1: 97 percent / imidazole / dimethylformamide / 3 h / 23 °C
3.1: 94 percent / K2CO3; MeOH / 2 h / 23 °C
4.1: Dess-Martin periodinane / CH2Cl2 / 0.33 h / 23 °C
5.1: 1.26 g / ZnCl2 / CH2Cl2; tetrahydrofuran / 0.17 h / 23 °C
6.1: 80 percent / LiBH4 / tetrahydrofuran; methanol / 10 h / 0 °C
7.1: 92 percent / pyridine; DMAP / CH2Cl2 / 0.5 h / 23 °C
8.1: 91 percent / aq. HF / acetonitrile / 2 h / 23 °C
9.1: 93 percent / Dess-Martin periodinane / CH2Cl2 / 0.33 h / 20 °C
10.1: 95 percent / CF3COOH / CH2Cl2 / 0.5 h / 23 °C
11.1: 96 percent / K2CO3; MeOH / 1 h / 20 °C
12.1: 95 percent / DMAP; EDCl / CH2Cl2 / 1 h / 20 °C
13.1: CF3COOH / 2,2,2-trifluoro-ethanol / 3 h / 20 °C
14.1: 143 mg / pyridine; DMAP / CH2Cl2 / 0.5 h / 23 °C
15.1: 87 percent / n-Bu3SnH; AcOH; Pd(PPh3)2Cl2 / CH2Cl2 / 0.33 h / 20 °C
16.1: 97 percent / NaBH3CN; AcOH / acetonitrile; methanol / 2 h / 23 °C
17.1: 92 percent / Zn; AcOH / diethyl ether / 1 h / 23 °C
18.1: 4-formyl-1-methylpyridinium benzenesulfonate / CH2Cl2; dimethylformamide / 0.17 h / 23 °C
18.2: DBU / CH2Cl2; dimethylformamide / 0.25 h / 23 °C
18.3: 53 percent / aq. oxalic acid / CH2Cl2; dimethylformamide / 0.5 h / 23 °C
19.1: 97 percent / NaOAc / ethanol / 3 h / 23 °C
20.1: 92 percent / aq. AgNO3 / acetonitrile / 19 h / 23 °C
View Scheme
1-(3-tert-butoxycarbonyl-2,2-dimethyl-oxazolidin-4-yl)-8-hydroxy-3-hydroxymethyl-7-methoxy-6-methyl-3,4-dihydro-1H-isoquinoline-2-carboxylic acid allyl ester
874758-71-1

1-(3-tert-butoxycarbonyl-2,2-dimethyl-oxazolidin-4-yl)-8-hydroxy-3-hydroxymethyl-7-methoxy-6-methyl-3,4-dihydro-1H-isoquinoline-2-carboxylic acid allyl ester

ecteinascidin 743
114899-77-3

ecteinascidin 743

Conditions
ConditionsYield
Multi-step reaction with 23 steps
1.1: 86 percent / Cs2CO3; CsI / dimethylformamide / 3 h / 20 °C
2.1: 92 percent / pyridine; DMAP / CH2Cl2 / 1 h / 20 °C
3.1: 72 percent / trfifluoroacetic acid / CH2Cl2 / 4 h / 20 °C
4.1: 68 percent / triethylamine / acetonitrile / 14 h / 0 °C
5.1: 97 percent / imidazole / dimethylformamide / 3 h / 23 °C
6.1: 94 percent / K2CO3; MeOH / 2 h / 23 °C
7.1: Dess-Martin periodinane / CH2Cl2 / 0.33 h / 23 °C
8.1: 1.26 g / ZnCl2 / CH2Cl2; tetrahydrofuran / 0.17 h / 23 °C
9.1: 80 percent / LiBH4 / tetrahydrofuran; methanol / 10 h / 0 °C
10.1: 92 percent / pyridine; DMAP / CH2Cl2 / 0.5 h / 23 °C
11.1: 91 percent / aq. HF / acetonitrile / 2 h / 23 °C
12.1: 93 percent / Dess-Martin periodinane / CH2Cl2 / 0.33 h / 20 °C
13.1: 95 percent / CF3COOH / CH2Cl2 / 0.5 h / 23 °C
14.1: 96 percent / K2CO3; MeOH / 1 h / 20 °C
15.1: 95 percent / DMAP; EDCl / CH2Cl2 / 1 h / 20 °C
16.1: CF3COOH / 2,2,2-trifluoro-ethanol / 3 h / 20 °C
17.1: 143 mg / pyridine; DMAP / CH2Cl2 / 0.5 h / 23 °C
18.1: 87 percent / n-Bu3SnH; AcOH; Pd(PPh3)2Cl2 / CH2Cl2 / 0.33 h / 20 °C
19.1: 97 percent / NaBH3CN; AcOH / acetonitrile; methanol / 2 h / 23 °C
20.1: 92 percent / Zn; AcOH / diethyl ether / 1 h / 23 °C
21.1: 4-formyl-1-methylpyridinium benzenesulfonate / CH2Cl2; dimethylformamide / 0.17 h / 23 °C
21.2: DBU / CH2Cl2; dimethylformamide / 0.25 h / 23 °C
21.3: 53 percent / aq. oxalic acid / CH2Cl2; dimethylformamide / 0.5 h / 23 °C
22.1: 97 percent / NaOAc / ethanol / 3 h / 23 °C
23.1: 92 percent / aq. AgNO3 / acetonitrile / 19 h / 23 °C
View Scheme
8-allyloxy-1-(3-tert-butoxycarbonyl-2,2-dimethyl-oxazolidin-4-yl)-3-hydroxymethyl-7-methoxy-6-methyl-3,4-dihydro-1H-isoquinoline-2-carboxylic acid allyl ester
874758-72-2

8-allyloxy-1-(3-tert-butoxycarbonyl-2,2-dimethyl-oxazolidin-4-yl)-3-hydroxymethyl-7-methoxy-6-methyl-3,4-dihydro-1H-isoquinoline-2-carboxylic acid allyl ester

ecteinascidin 743
114899-77-3

ecteinascidin 743

Conditions
ConditionsYield
Multi-step reaction with 22 steps
1.1: 92 percent / pyridine; DMAP / CH2Cl2 / 1 h / 20 °C
2.1: 72 percent / trfifluoroacetic acid / CH2Cl2 / 4 h / 20 °C
3.1: 68 percent / triethylamine / acetonitrile / 14 h / 0 °C
4.1: 97 percent / imidazole / dimethylformamide / 3 h / 23 °C
5.1: 94 percent / K2CO3; MeOH / 2 h / 23 °C
6.1: Dess-Martin periodinane / CH2Cl2 / 0.33 h / 23 °C
7.1: 1.26 g / ZnCl2 / CH2Cl2; tetrahydrofuran / 0.17 h / 23 °C
8.1: 80 percent / LiBH4 / tetrahydrofuran; methanol / 10 h / 0 °C
9.1: 92 percent / pyridine; DMAP / CH2Cl2 / 0.5 h / 23 °C
10.1: 91 percent / aq. HF / acetonitrile / 2 h / 23 °C
11.1: 93 percent / Dess-Martin periodinane / CH2Cl2 / 0.33 h / 20 °C
12.1: 95 percent / CF3COOH / CH2Cl2 / 0.5 h / 23 °C
13.1: 96 percent / K2CO3; MeOH / 1 h / 20 °C
14.1: 95 percent / DMAP; EDCl / CH2Cl2 / 1 h / 20 °C
15.1: CF3COOH / 2,2,2-trifluoro-ethanol / 3 h / 20 °C
16.1: 143 mg / pyridine; DMAP / CH2Cl2 / 0.5 h / 23 °C
17.1: 87 percent / n-Bu3SnH; AcOH; Pd(PPh3)2Cl2 / CH2Cl2 / 0.33 h / 20 °C
18.1: 97 percent / NaBH3CN; AcOH / acetonitrile; methanol / 2 h / 23 °C
19.1: 92 percent / Zn; AcOH / diethyl ether / 1 h / 23 °C
20.1: 4-formyl-1-methylpyridinium benzenesulfonate / CH2Cl2; dimethylformamide / 0.17 h / 23 °C
20.2: DBU / CH2Cl2; dimethylformamide / 0.25 h / 23 °C
20.3: 53 percent / aq. oxalic acid / CH2Cl2; dimethylformamide / 0.5 h / 23 °C
21.1: 97 percent / NaOAc / ethanol / 3 h / 23 °C
22.1: 92 percent / aq. AgNO3 / acetonitrile / 19 h / 23 °C
View Scheme
3-acetoxymethyl-8-allyloxy-1-(3-tert-butoxycarbonyl-2,2-dimethyl-oxazolidin-4-yl)-7-methoxy-6-methyl-3,4-dihydro-1H-isoquinoline-2-carboxylic acid allyl ester
874758-58-4

3-acetoxymethyl-8-allyloxy-1-(3-tert-butoxycarbonyl-2,2-dimethyl-oxazolidin-4-yl)-7-methoxy-6-methyl-3,4-dihydro-1H-isoquinoline-2-carboxylic acid allyl ester

ecteinascidin 743
114899-77-3

ecteinascidin 743

Conditions
ConditionsYield
Multi-step reaction with 21 steps
1.1: 72 percent / trfifluoroacetic acid / CH2Cl2 / 4 h / 20 °C
2.1: 68 percent / triethylamine / acetonitrile / 14 h / 0 °C
3.1: 97 percent / imidazole / dimethylformamide / 3 h / 23 °C
4.1: 94 percent / K2CO3; MeOH / 2 h / 23 °C
5.1: Dess-Martin periodinane / CH2Cl2 / 0.33 h / 23 °C
6.1: 1.26 g / ZnCl2 / CH2Cl2; tetrahydrofuran / 0.17 h / 23 °C
7.1: 80 percent / LiBH4 / tetrahydrofuran; methanol / 10 h / 0 °C
8.1: 92 percent / pyridine; DMAP / CH2Cl2 / 0.5 h / 23 °C
9.1: 91 percent / aq. HF / acetonitrile / 2 h / 23 °C
10.1: 93 percent / Dess-Martin periodinane / CH2Cl2 / 0.33 h / 20 °C
11.1: 95 percent / CF3COOH / CH2Cl2 / 0.5 h / 23 °C
12.1: 96 percent / K2CO3; MeOH / 1 h / 20 °C
13.1: 95 percent / DMAP; EDCl / CH2Cl2 / 1 h / 20 °C
14.1: CF3COOH / 2,2,2-trifluoro-ethanol / 3 h / 20 °C
15.1: 143 mg / pyridine; DMAP / CH2Cl2 / 0.5 h / 23 °C
16.1: 87 percent / n-Bu3SnH; AcOH; Pd(PPh3)2Cl2 / CH2Cl2 / 0.33 h / 20 °C
17.1: 97 percent / NaBH3CN; AcOH / acetonitrile; methanol / 2 h / 23 °C
18.1: 92 percent / Zn; AcOH / diethyl ether / 1 h / 23 °C
19.1: 4-formyl-1-methylpyridinium benzenesulfonate / CH2Cl2; dimethylformamide / 0.17 h / 23 °C
19.2: DBU / CH2Cl2; dimethylformamide / 0.25 h / 23 °C
19.3: 53 percent / aq. oxalic acid / CH2Cl2; dimethylformamide / 0.5 h / 23 °C
20.1: 97 percent / NaOAc / ethanol / 3 h / 23 °C
21.1: 92 percent / aq. AgNO3 / acetonitrile / 19 h / 23 °C
View Scheme
C32H35N3O9
874758-68-6

C32H35N3O9

ecteinascidin 743
114899-77-3

ecteinascidin 743

Conditions
ConditionsYield
Multi-step reaction with 9 steps
1.1: 95 percent / DMAP; EDCl / CH2Cl2 / 1 h / 20 °C
2.1: CF3COOH / 2,2,2-trifluoro-ethanol / 3 h / 20 °C
3.1: 143 mg / pyridine; DMAP / CH2Cl2 / 0.5 h / 23 °C
4.1: 87 percent / n-Bu3SnH; AcOH; Pd(PPh3)2Cl2 / CH2Cl2 / 0.33 h / 20 °C
5.1: 97 percent / NaBH3CN; AcOH / acetonitrile; methanol / 2 h / 23 °C
6.1: 92 percent / Zn; AcOH / diethyl ether / 1 h / 23 °C
7.1: 4-formyl-1-methylpyridinium benzenesulfonate / CH2Cl2; dimethylformamide / 0.17 h / 23 °C
7.2: DBU / CH2Cl2; dimethylformamide / 0.25 h / 23 °C
7.3: 53 percent / aq. oxalic acid / CH2Cl2; dimethylformamide / 0.5 h / 23 °C
8.1: 97 percent / NaOAc / ethanol / 3 h / 23 °C
9.1: 92 percent / aq. AgNO3 / acetonitrile / 19 h / 23 °C
View Scheme
Multi-step reaction with 9 steps
2: trifluoroacetic acid; polytetrafluoroethylene
3: acetic anhydride; pyridine; dmap
4: tri-n-butyl-tin hydride; bis-triphenylphosphine-palladium(II) chloride
6: zinc
7: C6H6NO(1+)*C7H7O3S(1-); 1,8-diazabicyclo[5.4.0]undec-7-ene; oxalic acid / dichloromethane; N,N-dimethyl-formamide / 20 °C
9: silver nitrate / acetonitrile; water / 20 °C
View Scheme
(1R,9S,10R,12R)-11-[(R)-2-Acetoxy-1-(6-methoxymethoxy-7-methyl-benzo[1,3]dioxol-4-yl)-ethyl]-3-allyloxy-10-cyano-12-formyl-4-methoxy-5-methyl-11,13-diaza-tricyclo[7.3.1.02,7]trideca-2,4,6-triene-13-carboxylic acid allyl ester
874758-66-4

(1R,9S,10R,12R)-11-[(R)-2-Acetoxy-1-(6-methoxymethoxy-7-methyl-benzo[1,3]dioxol-4-yl)-ethyl]-3-allyloxy-10-cyano-12-formyl-4-methoxy-5-methyl-11,13-diaza-tricyclo[7.3.1.02,7]trideca-2,4,6-triene-13-carboxylic acid allyl ester

ecteinascidin 743
114899-77-3

ecteinascidin 743

Conditions
ConditionsYield
Multi-step reaction with 11 steps
1.1: 95 percent / CF3COOH / CH2Cl2 / 0.5 h / 23 °C
2.1: 96 percent / K2CO3; MeOH / 1 h / 20 °C
3.1: 95 percent / DMAP; EDCl / CH2Cl2 / 1 h / 20 °C
4.1: CF3COOH / 2,2,2-trifluoro-ethanol / 3 h / 20 °C
5.1: 143 mg / pyridine; DMAP / CH2Cl2 / 0.5 h / 23 °C
6.1: 87 percent / n-Bu3SnH; AcOH; Pd(PPh3)2Cl2 / CH2Cl2 / 0.33 h / 20 °C
7.1: 97 percent / NaBH3CN; AcOH / acetonitrile; methanol / 2 h / 23 °C
8.1: 92 percent / Zn; AcOH / diethyl ether / 1 h / 23 °C
9.1: 4-formyl-1-methylpyridinium benzenesulfonate / CH2Cl2; dimethylformamide / 0.17 h / 23 °C
9.2: DBU / CH2Cl2; dimethylformamide / 0.25 h / 23 °C
9.3: 53 percent / aq. oxalic acid / CH2Cl2; dimethylformamide / 0.5 h / 23 °C
10.1: 97 percent / NaOAc / ethanol / 3 h / 23 °C
11.1: 92 percent / aq. AgNO3 / acetonitrile / 19 h / 23 °C
View Scheme
Multi-step reaction with 11 steps
1: trifluoroacetic acid / dichloromethane
2: potassium carbonate / methanol
4: trifluoroacetic acid; polytetrafluoroethylene
5: acetic anhydride; pyridine; dmap
6: tri-n-butyl-tin hydride; bis-triphenylphosphine-palladium(II) chloride
8: zinc
9: C6H6NO(1+)*C7H7O3S(1-); 1,8-diazabicyclo[5.4.0]undec-7-ene; oxalic acid / dichloromethane; N,N-dimethyl-formamide / 20 °C
11: silver nitrate / acetonitrile; water / 20 °C
View Scheme
(1R,9S,10R,12R)-11-[(R)-2-Acetoxy-1-(6-methoxymethoxy-7-methyl-benzo[1,3]dioxol-4-yl)-ethyl]-3-allyloxy-10-cyano-12-hydroxymethyl-4-methoxy-5-methyl-11,13-diaza-tricyclo[7.3.1.02,7]trideca-2,4,6-triene-13-carboxylic acid allyl ester
874758-78-8

(1R,9S,10R,12R)-11-[(R)-2-Acetoxy-1-(6-methoxymethoxy-7-methyl-benzo[1,3]dioxol-4-yl)-ethyl]-3-allyloxy-10-cyano-12-hydroxymethyl-4-methoxy-5-methyl-11,13-diaza-tricyclo[7.3.1.02,7]trideca-2,4,6-triene-13-carboxylic acid allyl ester

ecteinascidin 743
114899-77-3

ecteinascidin 743

Conditions
ConditionsYield
Multi-step reaction with 12 steps
1.1: 93 percent / Dess-Martin periodinane / CH2Cl2 / 0.33 h / 20 °C
2.1: 95 percent / CF3COOH / CH2Cl2 / 0.5 h / 23 °C
3.1: 96 percent / K2CO3; MeOH / 1 h / 20 °C
4.1: 95 percent / DMAP; EDCl / CH2Cl2 / 1 h / 20 °C
5.1: CF3COOH / 2,2,2-trifluoro-ethanol / 3 h / 20 °C
6.1: 143 mg / pyridine; DMAP / CH2Cl2 / 0.5 h / 23 °C
7.1: 87 percent / n-Bu3SnH; AcOH; Pd(PPh3)2Cl2 / CH2Cl2 / 0.33 h / 20 °C
8.1: 97 percent / NaBH3CN; AcOH / acetonitrile; methanol / 2 h / 23 °C
9.1: 92 percent / Zn; AcOH / diethyl ether / 1 h / 23 °C
10.1: 4-formyl-1-methylpyridinium benzenesulfonate / CH2Cl2; dimethylformamide / 0.17 h / 23 °C
10.2: DBU / CH2Cl2; dimethylformamide / 0.25 h / 23 °C
10.3: 53 percent / aq. oxalic acid / CH2Cl2; dimethylformamide / 0.5 h / 23 °C
11.1: 97 percent / NaOAc / ethanol / 3 h / 23 °C
12.1: 92 percent / aq. AgNO3 / acetonitrile / 19 h / 23 °C
View Scheme
Multi-step reaction with 12 steps
1: Dess-Martin periodane / dichloromethane
2: trifluoroacetic acid / dichloromethane
3: potassium carbonate / methanol
5: trifluoroacetic acid; polytetrafluoroethylene
6: acetic anhydride; pyridine; dmap
7: tri-n-butyl-tin hydride; bis-triphenylphosphine-palladium(II) chloride
9: zinc
10: C6H6NO(1+)*C7H7O3S(1-); 1,8-diazabicyclo[5.4.0]undec-7-ene; oxalic acid / dichloromethane; N,N-dimethyl-formamide / 20 °C
12: silver nitrate / acetonitrile; water / 20 °C
View Scheme
C34H37N3O10
874758-67-5

C34H37N3O10

ecteinascidin 743
114899-77-3

ecteinascidin 743

Conditions
ConditionsYield
Multi-step reaction with 10 steps
1.1: 96 percent / K2CO3; MeOH / 1 h / 20 °C
2.1: 95 percent / DMAP; EDCl / CH2Cl2 / 1 h / 20 °C
3.1: CF3COOH / 2,2,2-trifluoro-ethanol / 3 h / 20 °C
4.1: 143 mg / pyridine; DMAP / CH2Cl2 / 0.5 h / 23 °C
5.1: 87 percent / n-Bu3SnH; AcOH; Pd(PPh3)2Cl2 / CH2Cl2 / 0.33 h / 20 °C
6.1: 97 percent / NaBH3CN; AcOH / acetonitrile; methanol / 2 h / 23 °C
7.1: 92 percent / Zn; AcOH / diethyl ether / 1 h / 23 °C
8.1: 4-formyl-1-methylpyridinium benzenesulfonate / CH2Cl2; dimethylformamide / 0.17 h / 23 °C
8.2: DBU / CH2Cl2; dimethylformamide / 0.25 h / 23 °C
8.3: 53 percent / aq. oxalic acid / CH2Cl2; dimethylformamide / 0.5 h / 23 °C
9.1: 97 percent / NaOAc / ethanol / 3 h / 23 °C
10.1: 92 percent / aq. AgNO3 / acetonitrile / 19 h / 23 °C
View Scheme
Multi-step reaction with 10 steps
1: potassium carbonate / methanol
3: trifluoroacetic acid; polytetrafluoroethylene
4: acetic anhydride; pyridine; dmap
5: tri-n-butyl-tin hydride; bis-triphenylphosphine-palladium(II) chloride
7: zinc
8: C6H6NO(1+)*C7H7O3S(1-); 1,8-diazabicyclo[5.4.0]undec-7-ene; oxalic acid / dichloromethane; N,N-dimethyl-formamide / 20 °C
10: silver nitrate / acetonitrile; water / 20 °C
View Scheme
(1R,3S)-3-Acetoxymethyl-8-allyloxy-1-((R)-1-{[(R)-ethoxycarbonyl-(6-methoxymethoxy-7-methyl-benzo[1,3]dioxol-4-yl)-methyl]-amino}-2-hydroxy-ethyl)-7-methoxy-6-methyl-3,4-dihydro-1H-isoquinoline-2-carboxylic acid allyl ester
874758-61-9

(1R,3S)-3-Acetoxymethyl-8-allyloxy-1-((R)-1-{[(R)-ethoxycarbonyl-(6-methoxymethoxy-7-methyl-benzo[1,3]dioxol-4-yl)-methyl]-amino}-2-hydroxy-ethyl)-7-methoxy-6-methyl-3,4-dihydro-1H-isoquinoline-2-carboxylic acid allyl ester

ecteinascidin 743
114899-77-3

ecteinascidin 743

Conditions
ConditionsYield
Multi-step reaction with 19 steps
1.1: 97 percent / imidazole / dimethylformamide / 3 h / 23 °C
2.1: 94 percent / K2CO3; MeOH / 2 h / 23 °C
3.1: Dess-Martin periodinane / CH2Cl2 / 0.33 h / 23 °C
4.1: 1.26 g / ZnCl2 / CH2Cl2; tetrahydrofuran / 0.17 h / 23 °C
5.1: 80 percent / LiBH4 / tetrahydrofuran; methanol / 10 h / 0 °C
6.1: 92 percent / pyridine; DMAP / CH2Cl2 / 0.5 h / 23 °C
7.1: 91 percent / aq. HF / acetonitrile / 2 h / 23 °C
8.1: 93 percent / Dess-Martin periodinane / CH2Cl2 / 0.33 h / 20 °C
9.1: 95 percent / CF3COOH / CH2Cl2 / 0.5 h / 23 °C
10.1: 96 percent / K2CO3; MeOH / 1 h / 20 °C
11.1: 95 percent / DMAP; EDCl / CH2Cl2 / 1 h / 20 °C
12.1: CF3COOH / 2,2,2-trifluoro-ethanol / 3 h / 20 °C
13.1: 143 mg / pyridine; DMAP / CH2Cl2 / 0.5 h / 23 °C
14.1: 87 percent / n-Bu3SnH; AcOH; Pd(PPh3)2Cl2 / CH2Cl2 / 0.33 h / 20 °C
15.1: 97 percent / NaBH3CN; AcOH / acetonitrile; methanol / 2 h / 23 °C
16.1: 92 percent / Zn; AcOH / diethyl ether / 1 h / 23 °C
17.1: 4-formyl-1-methylpyridinium benzenesulfonate / CH2Cl2; dimethylformamide / 0.17 h / 23 °C
17.2: DBU / CH2Cl2; dimethylformamide / 0.25 h / 23 °C
17.3: 53 percent / aq. oxalic acid / CH2Cl2; dimethylformamide / 0.5 h / 23 °C
18.1: 97 percent / NaOAc / ethanol / 3 h / 23 °C
19.1: 92 percent / aq. AgNO3 / acetonitrile / 19 h / 23 °C
View Scheme
(1R,3S)-8-Allyloxy-1-((R)-2-(tert-butyl-dimethyl-silanyloxy)-1-{[(R)-ethoxycarbonyl-(6-methoxymethoxy-7-methyl-benzo[1,3]dioxol-4-yl)-methyl]-amino}-ethyl)-3-formyl-7-methoxy-6-methyl-3,4-dihydro-1H-isoquinoline-2-carboxylic acid allyl ester

(1R,3S)-8-Allyloxy-1-((R)-2-(tert-butyl-dimethyl-silanyloxy)-1-{[(R)-ethoxycarbonyl-(6-methoxymethoxy-7-methyl-benzo[1,3]dioxol-4-yl)-methyl]-amino}-ethyl)-3-formyl-7-methoxy-6-methyl-3,4-dihydro-1H-isoquinoline-2-carboxylic acid allyl ester

ecteinascidin 743
114899-77-3

ecteinascidin 743

Conditions
ConditionsYield
Multi-step reaction with 16 steps
1.1: 1.26 g / ZnCl2 / CH2Cl2; tetrahydrofuran / 0.17 h / 23 °C
2.1: 80 percent / LiBH4 / tetrahydrofuran; methanol / 10 h / 0 °C
3.1: 92 percent / pyridine; DMAP / CH2Cl2 / 0.5 h / 23 °C
4.1: 91 percent / aq. HF / acetonitrile / 2 h / 23 °C
5.1: 93 percent / Dess-Martin periodinane / CH2Cl2 / 0.33 h / 20 °C
6.1: 95 percent / CF3COOH / CH2Cl2 / 0.5 h / 23 °C
7.1: 96 percent / K2CO3; MeOH / 1 h / 20 °C
8.1: 95 percent / DMAP; EDCl / CH2Cl2 / 1 h / 20 °C
9.1: CF3COOH / 2,2,2-trifluoro-ethanol / 3 h / 20 °C
10.1: 143 mg / pyridine; DMAP / CH2Cl2 / 0.5 h / 23 °C
11.1: 87 percent / n-Bu3SnH; AcOH; Pd(PPh3)2Cl2 / CH2Cl2 / 0.33 h / 20 °C
12.1: 97 percent / NaBH3CN; AcOH / acetonitrile; methanol / 2 h / 23 °C
13.1: 92 percent / Zn; AcOH / diethyl ether / 1 h / 23 °C
14.1: 4-formyl-1-methylpyridinium benzenesulfonate / CH2Cl2; dimethylformamide / 0.17 h / 23 °C
14.2: DBU / CH2Cl2; dimethylformamide / 0.25 h / 23 °C
14.3: 53 percent / aq. oxalic acid / CH2Cl2; dimethylformamide / 0.5 h / 23 °C
15.1: 97 percent / NaOAc / ethanol / 3 h / 23 °C
16.1: 92 percent / aq. AgNO3 / acetonitrile / 19 h / 23 °C
View Scheme
3-allyloxy-12-(tert-butyl-dimethyl-silanyloxymethyl)-10-cyano-11-[2-hydroxy-1-(6-methoxymethoxy-7-methyl-benzo[1,3]dioxol-4-yl)-ethyl]-4-methoxy-5-methyl-11,13-diaza-tricyclo[7.3.1.02,7]trideca-2,4,6-triene-13-carboxylic acid allyl ester
874758-76-6

3-allyloxy-12-(tert-butyl-dimethyl-silanyloxymethyl)-10-cyano-11-[2-hydroxy-1-(6-methoxymethoxy-7-methyl-benzo[1,3]dioxol-4-yl)-ethyl]-4-methoxy-5-methyl-11,13-diaza-tricyclo[7.3.1.02,7]trideca-2,4,6-triene-13-carboxylic acid allyl ester

ecteinascidin 743
114899-77-3

ecteinascidin 743

Conditions
ConditionsYield
Multi-step reaction with 14 steps
1.1: 92 percent / pyridine; DMAP / CH2Cl2 / 0.5 h / 23 °C
2.1: 91 percent / aq. HF / acetonitrile / 2 h / 23 °C
3.1: 93 percent / Dess-Martin periodinane / CH2Cl2 / 0.33 h / 20 °C
4.1: 95 percent / CF3COOH / CH2Cl2 / 0.5 h / 23 °C
5.1: 96 percent / K2CO3; MeOH / 1 h / 20 °C
6.1: 95 percent / DMAP; EDCl / CH2Cl2 / 1 h / 20 °C
7.1: CF3COOH / 2,2,2-trifluoro-ethanol / 3 h / 20 °C
8.1: 143 mg / pyridine; DMAP / CH2Cl2 / 0.5 h / 23 °C
9.1: 87 percent / n-Bu3SnH; AcOH; Pd(PPh3)2Cl2 / CH2Cl2 / 0.33 h / 20 °C
10.1: 97 percent / NaBH3CN; AcOH / acetonitrile; methanol / 2 h / 23 °C
11.1: 92 percent / Zn; AcOH / diethyl ether / 1 h / 23 °C
12.1: 4-formyl-1-methylpyridinium benzenesulfonate / CH2Cl2; dimethylformamide / 0.17 h / 23 °C
12.2: DBU / CH2Cl2; dimethylformamide / 0.25 h / 23 °C
12.3: 53 percent / aq. oxalic acid / CH2Cl2; dimethylformamide / 0.5 h / 23 °C
13.1: 97 percent / NaOAc / ethanol / 3 h / 23 °C
14.1: 92 percent / aq. AgNO3 / acetonitrile / 19 h / 23 °C
View Scheme
Multi-step reaction with 13 steps
1: pyridine; dmap
2: Dess-Martin periodane / dichloromethane
3: trifluoroacetic acid / dichloromethane
4: potassium carbonate / methanol
6: trifluoroacetic acid; polytetrafluoroethylene
7: acetic anhydride; pyridine; dmap
8: tri-n-butyl-tin hydride; bis-triphenylphosphine-palladium(II) chloride
10: zinc
11: C6H6NO(1+)*C7H7O3S(1-); 1,8-diazabicyclo[5.4.0]undec-7-ene; oxalic acid / dichloromethane; N,N-dimethyl-formamide / 20 °C
13: silver nitrate / acetonitrile; water / 20 °C
View Scheme
(1R,3S)-8-Allyloxy-1-((R)-2-(tert-butyl-dimethyl-silanyloxy)-1-{[(R)-ethoxycarbonyl-(6-methoxymethoxy-7-methyl-benzo[1,3]dioxol-4-yl)-methyl]-amino}-ethyl)-3-hydroxymethyl-7-methoxy-6-methyl-3,4-dihydro-1H-isoquinoline-2-carboxylic acid allyl ester
874758-63-1

(1R,3S)-8-Allyloxy-1-((R)-2-(tert-butyl-dimethyl-silanyloxy)-1-{[(R)-ethoxycarbonyl-(6-methoxymethoxy-7-methyl-benzo[1,3]dioxol-4-yl)-methyl]-amino}-ethyl)-3-hydroxymethyl-7-methoxy-6-methyl-3,4-dihydro-1H-isoquinoline-2-carboxylic acid allyl ester

ecteinascidin 743
114899-77-3

ecteinascidin 743

Conditions
ConditionsYield
Multi-step reaction with 17 steps
1.1: Dess-Martin periodinane / CH2Cl2 / 0.33 h / 23 °C
2.1: 1.26 g / ZnCl2 / CH2Cl2; tetrahydrofuran / 0.17 h / 23 °C
3.1: 80 percent / LiBH4 / tetrahydrofuran; methanol / 10 h / 0 °C
4.1: 92 percent / pyridine; DMAP / CH2Cl2 / 0.5 h / 23 °C
5.1: 91 percent / aq. HF / acetonitrile / 2 h / 23 °C
6.1: 93 percent / Dess-Martin periodinane / CH2Cl2 / 0.33 h / 20 °C
7.1: 95 percent / CF3COOH / CH2Cl2 / 0.5 h / 23 °C
8.1: 96 percent / K2CO3; MeOH / 1 h / 20 °C
9.1: 95 percent / DMAP; EDCl / CH2Cl2 / 1 h / 20 °C
10.1: CF3COOH / 2,2,2-trifluoro-ethanol / 3 h / 20 °C
11.1: 143 mg / pyridine; DMAP / CH2Cl2 / 0.5 h / 23 °C
12.1: 87 percent / n-Bu3SnH; AcOH; Pd(PPh3)2Cl2 / CH2Cl2 / 0.33 h / 20 °C
13.1: 97 percent / NaBH3CN; AcOH / acetonitrile; methanol / 2 h / 23 °C
14.1: 92 percent / Zn; AcOH / diethyl ether / 1 h / 23 °C
15.1: 4-formyl-1-methylpyridinium benzenesulfonate / CH2Cl2; dimethylformamide / 0.17 h / 23 °C
15.2: DBU / CH2Cl2; dimethylformamide / 0.25 h / 23 °C
15.3: 53 percent / aq. oxalic acid / CH2Cl2; dimethylformamide / 0.5 h / 23 °C
16.1: 97 percent / NaOAc / ethanol / 3 h / 23 °C
17.1: 92 percent / aq. AgNO3 / acetonitrile / 19 h / 23 °C
View Scheme
C34H35Cl3N4O10S
366020-69-1

C34H35Cl3N4O10S

ecteinascidin 743
114899-77-3

ecteinascidin 743

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: 92 percent / Zn; AcOH / diethyl ether / 1 h / 23 °C
2.1: 4-formyl-1-methylpyridinium benzenesulfonate / CH2Cl2; dimethylformamide / 0.17 h / 23 °C
2.2: DBU / CH2Cl2; dimethylformamide / 0.25 h / 23 °C
2.3: 53 percent / aq. oxalic acid / CH2Cl2; dimethylformamide / 0.5 h / 23 °C
3.1: 97 percent / NaOAc / ethanol / 3 h / 23 °C
4.1: 92 percent / aq. AgNO3 / acetonitrile / 19 h / 23 °C
View Scheme
Multi-step reaction with 4 steps
1: zinc
2: C6H6NO(1+)*C7H7O3S(1-); 1,8-diazabicyclo[5.4.0]undec-7-ene; oxalic acid / dichloromethane; N,N-dimethyl-formamide / 20 °C
4: silver nitrate / acetonitrile; water / 20 °C
View Scheme
Multi-step reaction with 5 steps
1.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 2 h / 0 - 5 °C
2.1: zinc / tetrahydrofuran; methanol; aq. phosphate buffer / 25 - 30 °C
3.1: zinc(II) sulfate; magnesium glyoxylate / acetonitrile / 1 h / 20 - 25 °C
4.1: acetic acid / ethanol / 5 h / 20 - 25 °C
5.1: trifluoroacetic acid / tetrahydrofuran; water / 16 h / 20 - 25 °C
5.2: 18 h / 20 - 25 °C
View Scheme
3-allyloxy-12-(tert-butyl-dimethyl-silanyloxymethyl)-10-cyano-11-[ethoxycarbonyl-(6-methoxymethoxy-7-methyl-benzo[1,3]dioxol-4-yl)-methyl]-4-methoxy-5-methyl-11,13-diaza-tricyclo[7.3.1.02,7]trideca-2,4,6-triene-13-carboxylic acid allyl ester
874758-64-2

3-allyloxy-12-(tert-butyl-dimethyl-silanyloxymethyl)-10-cyano-11-[ethoxycarbonyl-(6-methoxymethoxy-7-methyl-benzo[1,3]dioxol-4-yl)-methyl]-4-methoxy-5-methyl-11,13-diaza-tricyclo[7.3.1.02,7]trideca-2,4,6-triene-13-carboxylic acid allyl ester

ecteinascidin 743
114899-77-3

ecteinascidin 743

Conditions
ConditionsYield
Multi-step reaction with 15 steps
1.1: 80 percent / LiBH4 / tetrahydrofuran; methanol / 10 h / 0 °C
2.1: 92 percent / pyridine; DMAP / CH2Cl2 / 0.5 h / 23 °C
3.1: 91 percent / aq. HF / acetonitrile / 2 h / 23 °C
4.1: 93 percent / Dess-Martin periodinane / CH2Cl2 / 0.33 h / 20 °C
5.1: 95 percent / CF3COOH / CH2Cl2 / 0.5 h / 23 °C
6.1: 96 percent / K2CO3; MeOH / 1 h / 20 °C
7.1: 95 percent / DMAP; EDCl / CH2Cl2 / 1 h / 20 °C
8.1: CF3COOH / 2,2,2-trifluoro-ethanol / 3 h / 20 °C
9.1: 143 mg / pyridine; DMAP / CH2Cl2 / 0.5 h / 23 °C
10.1: 87 percent / n-Bu3SnH; AcOH; Pd(PPh3)2Cl2 / CH2Cl2 / 0.33 h / 20 °C
11.1: 97 percent / NaBH3CN; AcOH / acetonitrile; methanol / 2 h / 23 °C
12.1: 92 percent / Zn; AcOH / diethyl ether / 1 h / 23 °C
13.1: 4-formyl-1-methylpyridinium benzenesulfonate / CH2Cl2; dimethylformamide / 0.17 h / 23 °C
13.2: DBU / CH2Cl2; dimethylformamide / 0.25 h / 23 °C
13.3: 53 percent / aq. oxalic acid / CH2Cl2; dimethylformamide / 0.5 h / 23 °C
14.1: 97 percent / NaOAc / ethanol / 3 h / 23 °C
15.1: 92 percent / aq. AgNO3 / acetonitrile / 19 h / 23 °C
View Scheme
Multi-step reaction with 14 steps
1: lithium borohydride / methanol; tetrahydrofuran / 10 h / 0 °C
2: pyridine; dmap
3: Dess-Martin periodane / dichloromethane
4: trifluoroacetic acid / dichloromethane
5: potassium carbonate / methanol
7: trifluoroacetic acid; polytetrafluoroethylene
8: acetic anhydride; pyridine; dmap
9: tri-n-butyl-tin hydride; bis-triphenylphosphine-palladium(II) chloride
11: zinc
12: C6H6NO(1+)*C7H7O3S(1-); 1,8-diazabicyclo[5.4.0]undec-7-ene; oxalic acid / dichloromethane; N,N-dimethyl-formamide / 20 °C
14: silver nitrate / acetonitrile; water / 20 °C
View Scheme
11-[2-acetoxy-1-(6-methoxymethoxy-7-methyl-benzo[1,3]dioxol-4-yl)-ethyl]-3-allyloxy-12-(tert-butyl-dimethyl-silanyloxymethyl)-10-cyano-4-methoxy-5-methyl-11,13-diaza-tricyclo[7.3.1.02,7]trideca-2,4,6-triene-13-carboxylic acid allyl ester
874758-65-3

11-[2-acetoxy-1-(6-methoxymethoxy-7-methyl-benzo[1,3]dioxol-4-yl)-ethyl]-3-allyloxy-12-(tert-butyl-dimethyl-silanyloxymethyl)-10-cyano-4-methoxy-5-methyl-11,13-diaza-tricyclo[7.3.1.02,7]trideca-2,4,6-triene-13-carboxylic acid allyl ester

ecteinascidin 743
114899-77-3

ecteinascidin 743

Conditions
ConditionsYield
Multi-step reaction with 13 steps
1.1: 91 percent / aq. HF / acetonitrile / 2 h / 23 °C
2.1: 93 percent / Dess-Martin periodinane / CH2Cl2 / 0.33 h / 20 °C
3.1: 95 percent / CF3COOH / CH2Cl2 / 0.5 h / 23 °C
4.1: 96 percent / K2CO3; MeOH / 1 h / 20 °C
5.1: 95 percent / DMAP; EDCl / CH2Cl2 / 1 h / 20 °C
6.1: CF3COOH / 2,2,2-trifluoro-ethanol / 3 h / 20 °C
7.1: 143 mg / pyridine; DMAP / CH2Cl2 / 0.5 h / 23 °C
8.1: 87 percent / n-Bu3SnH; AcOH; Pd(PPh3)2Cl2 / CH2Cl2 / 0.33 h / 20 °C
9.1: 97 percent / NaBH3CN; AcOH / acetonitrile; methanol / 2 h / 23 °C
10.1: 92 percent / Zn; AcOH / diethyl ether / 1 h / 23 °C
11.1: 4-formyl-1-methylpyridinium benzenesulfonate / CH2Cl2; dimethylformamide / 0.17 h / 23 °C
11.2: DBU / CH2Cl2; dimethylformamide / 0.25 h / 23 °C
11.3: 53 percent / aq. oxalic acid / CH2Cl2; dimethylformamide / 0.5 h / 23 °C
12.1: 97 percent / NaOAc / ethanol / 3 h / 23 °C
13.1: 92 percent / aq. AgNO3 / acetonitrile / 19 h / 23 °C
View Scheme
Multi-step reaction with 13 steps
1: hydrogen fluoride / water
2: Dess-Martin periodane / dichloromethane
3: trifluoroacetic acid / dichloromethane
4: potassium carbonate / methanol
6: trifluoroacetic acid; polytetrafluoroethylene
7: acetic anhydride; pyridine; dmap
8: tri-n-butyl-tin hydride; bis-triphenylphosphine-palladium(II) chloride
10: zinc
11: C6H6NO(1+)*C7H7O3S(1-); 1,8-diazabicyclo[5.4.0]undec-7-ene; oxalic acid / dichloromethane; N,N-dimethyl-formamide / 20 °C
13: silver nitrate / acetonitrile; water / 20 °C
View Scheme
(1R,3S)-3-Acetoxymethyl-8-allyloxy-1-((R)-2-(tert-butyl-dimethyl-silanyloxy)-1-{[(R)-ethoxycarbonyl-(6-methoxymethoxy-7-methyl-benzo[1,3]dioxol-4-yl)-methyl]-amino}-ethyl)-7-methoxy-6-methyl-3,4-dihydro-1H-isoquinoline-2-carboxylic acid allyl ester
874758-73-3

(1R,3S)-3-Acetoxymethyl-8-allyloxy-1-((R)-2-(tert-butyl-dimethyl-silanyloxy)-1-{[(R)-ethoxycarbonyl-(6-methoxymethoxy-7-methyl-benzo[1,3]dioxol-4-yl)-methyl]-amino}-ethyl)-7-methoxy-6-methyl-3,4-dihydro-1H-isoquinoline-2-carboxylic acid allyl ester

ecteinascidin 743
114899-77-3

ecteinascidin 743

Conditions
ConditionsYield
Multi-step reaction with 18 steps
1.1: 94 percent / K2CO3; MeOH / 2 h / 23 °C
2.1: Dess-Martin periodinane / CH2Cl2 / 0.33 h / 23 °C
3.1: 1.26 g / ZnCl2 / CH2Cl2; tetrahydrofuran / 0.17 h / 23 °C
4.1: 80 percent / LiBH4 / tetrahydrofuran; methanol / 10 h / 0 °C
5.1: 92 percent / pyridine; DMAP / CH2Cl2 / 0.5 h / 23 °C
6.1: 91 percent / aq. HF / acetonitrile / 2 h / 23 °C
7.1: 93 percent / Dess-Martin periodinane / CH2Cl2 / 0.33 h / 20 °C
8.1: 95 percent / CF3COOH / CH2Cl2 / 0.5 h / 23 °C
9.1: 96 percent / K2CO3; MeOH / 1 h / 20 °C
10.1: 95 percent / DMAP; EDCl / CH2Cl2 / 1 h / 20 °C
11.1: CF3COOH / 2,2,2-trifluoro-ethanol / 3 h / 20 °C
12.1: 143 mg / pyridine; DMAP / CH2Cl2 / 0.5 h / 23 °C
13.1: 87 percent / n-Bu3SnH; AcOH; Pd(PPh3)2Cl2 / CH2Cl2 / 0.33 h / 20 °C
14.1: 97 percent / NaBH3CN; AcOH / acetonitrile; methanol / 2 h / 23 °C
15.1: 92 percent / Zn; AcOH / diethyl ether / 1 h / 23 °C
16.1: 4-formyl-1-methylpyridinium benzenesulfonate / CH2Cl2; dimethylformamide / 0.17 h / 23 °C
16.2: DBU / CH2Cl2; dimethylformamide / 0.25 h / 23 °C
16.3: 53 percent / aq. oxalic acid / CH2Cl2; dimethylformamide / 0.5 h / 23 °C
17.1: 97 percent / NaOAc / ethanol / 3 h / 23 °C
18.1: 92 percent / aq. AgNO3 / acetonitrile / 19 h / 23 °C
View Scheme
C33H33Cl3N4O10S
874758-82-4

C33H33Cl3N4O10S

ecteinascidin 743
114899-77-3

ecteinascidin 743

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: 97 percent / NaBH3CN; AcOH / acetonitrile; methanol / 2 h / 23 °C
2.1: 92 percent / Zn; AcOH / diethyl ether / 1 h / 23 °C
3.1: 4-formyl-1-methylpyridinium benzenesulfonate / CH2Cl2; dimethylformamide / 0.17 h / 23 °C
3.2: DBU / CH2Cl2; dimethylformamide / 0.25 h / 23 °C
3.3: 53 percent / aq. oxalic acid / CH2Cl2; dimethylformamide / 0.5 h / 23 °C
4.1: 97 percent / NaOAc / ethanol / 3 h / 23 °C
5.1: 92 percent / aq. AgNO3 / acetonitrile / 19 h / 23 °C
View Scheme
Multi-step reaction with 5 steps
2: zinc
3: C6H6NO(1+)*C7H7O3S(1-); 1,8-diazabicyclo[5.4.0]undec-7-ene; oxalic acid / dichloromethane; N,N-dimethyl-formamide / 20 °C
5: silver nitrate / acetonitrile; water / 20 °C
View Scheme
C38H39Cl3N4O11S
1054622-74-0

C38H39Cl3N4O11S

ecteinascidin 743
114899-77-3

ecteinascidin 743

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1.1: 143 mg / pyridine; DMAP / CH2Cl2 / 0.5 h / 23 °C
2.1: 87 percent / n-Bu3SnH; AcOH; Pd(PPh3)2Cl2 / CH2Cl2 / 0.33 h / 20 °C
3.1: 97 percent / NaBH3CN; AcOH / acetonitrile; methanol / 2 h / 23 °C
4.1: 92 percent / Zn; AcOH / diethyl ether / 1 h / 23 °C
5.1: 4-formyl-1-methylpyridinium benzenesulfonate / CH2Cl2; dimethylformamide / 0.17 h / 23 °C
5.2: DBU / CH2Cl2; dimethylformamide / 0.25 h / 23 °C
5.3: 53 percent / aq. oxalic acid / CH2Cl2; dimethylformamide / 0.5 h / 23 °C
6.1: 97 percent / NaOAc / ethanol / 3 h / 23 °C
7.1: 92 percent / aq. AgNO3 / acetonitrile / 19 h / 23 °C
View Scheme
Multi-step reaction with 7 steps
1: acetic anhydride; pyridine; dmap
2: tri-n-butyl-tin hydride; bis-triphenylphosphine-palladium(II) chloride
4: zinc
5: C6H6NO(1+)*C7H7O3S(1-); 1,8-diazabicyclo[5.4.0]undec-7-ene; oxalic acid / dichloromethane; N,N-dimethyl-formamide / 20 °C
7: silver nitrate / acetonitrile; water / 20 °C
View Scheme
C40H41Cl3N4O12S
874758-70-0

C40H41Cl3N4O12S

ecteinascidin 743
114899-77-3

ecteinascidin 743

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: 87 percent / n-Bu3SnH; AcOH; Pd(PPh3)2Cl2 / CH2Cl2 / 0.33 h / 20 °C
2.1: 97 percent / NaBH3CN; AcOH / acetonitrile; methanol / 2 h / 23 °C
3.1: 92 percent / Zn; AcOH / diethyl ether / 1 h / 23 °C
4.1: 4-formyl-1-methylpyridinium benzenesulfonate / CH2Cl2; dimethylformamide / 0.17 h / 23 °C
4.2: DBU / CH2Cl2; dimethylformamide / 0.25 h / 23 °C
4.3: 53 percent / aq. oxalic acid / CH2Cl2; dimethylformamide / 0.5 h / 23 °C
5.1: 97 percent / NaOAc / ethanol / 3 h / 23 °C
6.1: 92 percent / aq. AgNO3 / acetonitrile / 19 h / 23 °C
View Scheme
Multi-step reaction with 6 steps
1: tri-n-butyl-tin hydride; bis-triphenylphosphine-palladium(II) chloride
3: zinc
4: C6H6NO(1+)*C7H7O3S(1-); 1,8-diazabicyclo[5.4.0]undec-7-ene; oxalic acid / dichloromethane; N,N-dimethyl-formamide / 20 °C
6: silver nitrate / acetonitrile; water / 20 °C
View Scheme
C60H61Cl3N4O15S
874758-69-7

C60H61Cl3N4O15S

ecteinascidin 743
114899-77-3

ecteinascidin 743

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1.1: CF3COOH / 2,2,2-trifluoro-ethanol / 3 h / 20 °C
2.1: 143 mg / pyridine; DMAP / CH2Cl2 / 0.5 h / 23 °C
3.1: 87 percent / n-Bu3SnH; AcOH; Pd(PPh3)2Cl2 / CH2Cl2 / 0.33 h / 20 °C
4.1: 97 percent / NaBH3CN; AcOH / acetonitrile; methanol / 2 h / 23 °C
5.1: 92 percent / Zn; AcOH / diethyl ether / 1 h / 23 °C
6.1: 4-formyl-1-methylpyridinium benzenesulfonate / CH2Cl2; dimethylformamide / 0.17 h / 23 °C
6.2: DBU / CH2Cl2; dimethylformamide / 0.25 h / 23 °C
6.3: 53 percent / aq. oxalic acid / CH2Cl2; dimethylformamide / 0.5 h / 23 °C
7.1: 97 percent / NaOAc / ethanol / 3 h / 23 °C
8.1: 92 percent / aq. AgNO3 / acetonitrile / 19 h / 23 °C
View Scheme
Sesamol
533-31-3

Sesamol

ecteinascidin 743
114899-77-3

ecteinascidin 743

Conditions
ConditionsYield
Multi-step reaction with 26 steps
1.1: 96 percent / NaH / diethyl ether; dimethylformamide / 0 - 20 °C
2.1: n-BuLi; B(OMe)3 / tetrahydrofuran
2.2: 95 percent / AcOH; H2O2 / 0 - 20 °C
3.1: 97 percent / LiCl; 3 Angstroem molecular sieves / toluene; various solvent(s) / 24 h / 20 °C
4.1: 95 percent / K2CO3 / dimethylformamide / 1 h / 23 °C
5.1: 93 percent / K3PO4; Pd(PPh3)4 / dioxane / 4 h / 100 °C
6.1: 91 percent / benzotriazole; thionyl bromide / CH2Cl2 / 0.33 h / 20 °C
7.1: 68 percent / triethylamine / acetonitrile / 14 h / 0 °C
8.1: 97 percent / imidazole / dimethylformamide / 3 h / 23 °C
9.1: 94 percent / K2CO3; MeOH / 2 h / 23 °C
10.1: Dess-Martin periodinane / CH2Cl2 / 0.33 h / 23 °C
11.1: 1.26 g / ZnCl2 / CH2Cl2; tetrahydrofuran / 0.17 h / 23 °C
12.1: 80 percent / LiBH4 / tetrahydrofuran; methanol / 10 h / 0 °C
13.1: 92 percent / pyridine; DMAP / CH2Cl2 / 0.5 h / 23 °C
14.1: 91 percent / aq. HF / acetonitrile / 2 h / 23 °C
15.1: 93 percent / Dess-Martin periodinane / CH2Cl2 / 0.33 h / 20 °C
16.1: 95 percent / CF3COOH / CH2Cl2 / 0.5 h / 23 °C
17.1: 96 percent / K2CO3; MeOH / 1 h / 20 °C
18.1: 95 percent / DMAP; EDCl / CH2Cl2 / 1 h / 20 °C
19.1: CF3COOH / 2,2,2-trifluoro-ethanol / 3 h / 20 °C
20.1: 143 mg / pyridine; DMAP / CH2Cl2 / 0.5 h / 23 °C
21.1: 87 percent / n-Bu3SnH; AcOH; Pd(PPh3)2Cl2 / CH2Cl2 / 0.33 h / 20 °C
22.1: 97 percent / NaBH3CN; AcOH / acetonitrile; methanol / 2 h / 23 °C
23.1: 92 percent / Zn; AcOH / diethyl ether / 1 h / 23 °C
24.1: 4-formyl-1-methylpyridinium benzenesulfonate / CH2Cl2; dimethylformamide / 0.17 h / 23 °C
24.2: DBU / CH2Cl2; dimethylformamide / 0.25 h / 23 °C
24.3: 53 percent / aq. oxalic acid / CH2Cl2; dimethylformamide / 0.5 h / 23 °C
25.1: 97 percent / NaOAc / ethanol / 3 h / 23 °C
26.1: 92 percent / aq. AgNO3 / acetonitrile / 19 h / 23 °C
View Scheme
Multi-step reaction with 47 steps
1.1: NaH / tetrahydrofuran; dimethylformamide; various solvent(s) / 0 - 20 °C
1.2: 97 percent / tetrahydrofuran; dimethylformamide; various solvent(s) / 0 - 20 °C
2.1: n-BuLi / tetrahydrofuran; hexane / 0 - 20 °C
2.2: 92 percent / aq. H2O2; trimethylboronate; AcOH / tetrahydrofuran; hexane / 4.5 h / 20 °C
3.1: 89 percent / TFA / CH2Cl2 / 2.17 h / -10 °C
4.1: 90 percent / pyridine / CH2Cl2 / 0.08 h / 0 °C
5.1: 85 percent / NaBH4 / methanol / 0.5 h / 0 °C
6.1: 91 percent / imidazole / dimethylformamide / 20 °C
7.1: 97 percent / PdCl2(dppf) / tetrahydrofuran / 4.5 h / Heating
8.1: Pb(OAc)4 / acetonitrile / 0 °C
9.1: 436 mg / NH2OH*HCl; NaOAc / ethanol / 1.5 h / 20 °C
10.1: 90 percent / methanol / 1 h / Heating
11.1: 89 percent / TBAF / tetrahydrofuran / 0.5 h / 20 °C
12.1: 93 percent / pyridine; DMAP / 30 h / 50 °C
13.1: TFA; anisole / CH2Cl2 / 9 h / 20 °C
14.1: 19.7 g / ethyl acetate / 1 h / Heating
15.1: 91 percent / TEA / CH2Cl2 / 1 h / 0 °C
16.1: 97 percent / DMAP / acetonitrile / 6.5 h / 20 °C
17.1: NaBH4; H2SO4 / ethanol; CH2Cl2 / 0 °C
18.1: 3.54 g / CSA; quinoline / toluene / 3 h / Heating
19.1: 83 percent / tris(dibenzylideneacetone)dipalladium(0); tris(o-tolyl)phosphine; TEA / acetonitrile / 2 h / Heating
20.1: aq. NaOH / methanol / 2.5 h / Heating
21.1: 106 mg / pyridine; DMAP / CH2Cl2 / 20 °C
22.1: TFA / CH2Cl2 / 4 h / 20 °C
23.1: 2.08 g / NaHCO3 / CH2Cl2; H2O / 0.17 h / 0 °C
24.1: dimethyldioxirane / methanol; acetone / 2 h / 0 °C
25.1: 652 mg / CSA / acetone / 0 - 20 °C
26.1: 94 percent / sodium cyanoborohydride; TFA / tetrahydrofuran / 0.5 h / 0 °C
27.1: 92 percent / imidazole / dimethylformamide / 2 h / 20 °C
28.1: 85 percent / guanidinium nitrate; NaOMe / methanol; CH2Cl2 / 2.5 h / 40 °C
29.1: 91 percent / K2CO3 / acetonitrile / 1 h / Heating
30.1: 82 percent / Red-Al / tetrahydrofuran; toluene / 0 °C
31.1: 73 percent / BF3*OEt2 / CH2Cl2 / 0 °C
32.1: 92 percent / pyridine; DMAP / 20 °C
33.1: 100 percent / aq. HF / acetonitrile / 3 h / 20 °C
34.1: 92 percent / Dess-Martin periodinane / CH2Cl2 / 0.67 h / 20 °C
35.1: 84 percent / H2 / Pd/C / tetrahydrofuran / 18 h / 20 °C / 760.05 Torr
36.1: 89 percent / i-Pr2NEt / CH2Cl2 / 3 h / Heating
37.1: 99 percent / K2CO3 / methanol / 0.5 h / 20 °C
38.1: 94 percent / WSCD*HCl; DMAP / CH2Cl2 / 0.17 h / 20 °C
39.1: 98 percent / hydrazine / acetonitrile / 1.33 h / 20 °C
40.1: TFA / 2,2,2-trifluoro-ethanol / 3 h / 20 °C
41.1: 18.0 mg / pyridine; DMAP / 0.5 h / 20 °C
42.1: 92 percent / Zn; AcOH / diethyl ether / 2.5 h / 20 °C
43.1: 96 percent / AcOH; sodium cyanoborohydride / methanol / 1 h / 20 °C
44.1: 89 percent / Pd(PPh3)2Cl2; AcOH; n-Bu3SnH / CH2Cl2 / 0.33 h / 20 °C
45.1: 4-formyl-1-methylpyridinium benzenesulfonate / dimethylformamide; CH2Cl2 / 0.25 h / 20 °C
45.2: DBU / dimethylformamide; CH2Cl2 / 0.42 h / 20 °C
45.3: 54 percent / aq. citric acid / CH2Cl2; dimethylformamide / 0.67 h / 20 °C
46.1: 96 percent / sodium acetate / ethanol / 5.5 h / 20 °C
47.1: 93 percent / silver nitrate / acetoni
View Scheme
(3,4-methylenedioxyphenoxy)methyl methyl ether
111726-43-3

(3,4-methylenedioxyphenoxy)methyl methyl ether

ecteinascidin 743
114899-77-3

ecteinascidin 743

Conditions
ConditionsYield
Multi-step reaction with 25 steps
1.1: n-BuLi; B(OMe)3 / tetrahydrofuran
1.2: 95 percent / AcOH; H2O2 / 0 - 20 °C
2.1: 97 percent / LiCl; 3 Angstroem molecular sieves / toluene; various solvent(s) / 24 h / 20 °C
3.1: 95 percent / K2CO3 / dimethylformamide / 1 h / 23 °C
4.1: 93 percent / K3PO4; Pd(PPh3)4 / dioxane / 4 h / 100 °C
5.1: 91 percent / benzotriazole; thionyl bromide / CH2Cl2 / 0.33 h / 20 °C
6.1: 68 percent / triethylamine / acetonitrile / 14 h / 0 °C
7.1: 97 percent / imidazole / dimethylformamide / 3 h / 23 °C
8.1: 94 percent / K2CO3; MeOH / 2 h / 23 °C
9.1: Dess-Martin periodinane / CH2Cl2 / 0.33 h / 23 °C
10.1: 1.26 g / ZnCl2 / CH2Cl2; tetrahydrofuran / 0.17 h / 23 °C
11.1: 80 percent / LiBH4 / tetrahydrofuran; methanol / 10 h / 0 °C
12.1: 92 percent / pyridine; DMAP / CH2Cl2 / 0.5 h / 23 °C
13.1: 91 percent / aq. HF / acetonitrile / 2 h / 23 °C
14.1: 93 percent / Dess-Martin periodinane / CH2Cl2 / 0.33 h / 20 °C
15.1: 95 percent / CF3COOH / CH2Cl2 / 0.5 h / 23 °C
16.1: 96 percent / K2CO3; MeOH / 1 h / 20 °C
17.1: 95 percent / DMAP; EDCl / CH2Cl2 / 1 h / 20 °C
18.1: CF3COOH / 2,2,2-trifluoro-ethanol / 3 h / 20 °C
19.1: 143 mg / pyridine; DMAP / CH2Cl2 / 0.5 h / 23 °C
20.1: 87 percent / n-Bu3SnH; AcOH; Pd(PPh3)2Cl2 / CH2Cl2 / 0.33 h / 20 °C
21.1: 97 percent / NaBH3CN; AcOH / acetonitrile; methanol / 2 h / 23 °C
22.1: 92 percent / Zn; AcOH / diethyl ether / 1 h / 23 °C
23.1: 4-formyl-1-methylpyridinium benzenesulfonate / CH2Cl2; dimethylformamide / 0.17 h / 23 °C
23.2: DBU / CH2Cl2; dimethylformamide / 0.25 h / 23 °C
23.3: 53 percent / aq. oxalic acid / CH2Cl2; dimethylformamide / 0.5 h / 23 °C
24.1: 97 percent / NaOAc / ethanol / 3 h / 23 °C
25.1: 92 percent / aq. AgNO3 / acetonitrile / 19 h / 23 °C
View Scheme
Multi-step reaction with 46 steps
1.1: n-BuLi / tetrahydrofuran; hexane / 0 - 20 °C
1.2: 92 percent / aq. H2O2; trimethylboronate; AcOH / tetrahydrofuran; hexane / 4.5 h / 20 °C
2.1: 89 percent / TFA / CH2Cl2 / 2.17 h / -10 °C
3.1: 90 percent / pyridine / CH2Cl2 / 0.08 h / 0 °C
4.1: 85 percent / NaBH4 / methanol / 0.5 h / 0 °C
5.1: 91 percent / imidazole / dimethylformamide / 20 °C
6.1: 97 percent / PdCl2(dppf) / tetrahydrofuran / 4.5 h / Heating
7.1: Pb(OAc)4 / acetonitrile / 0 °C
8.1: 436 mg / NH2OH*HCl; NaOAc / ethanol / 1.5 h / 20 °C
9.1: 90 percent / methanol / 1 h / Heating
10.1: 89 percent / TBAF / tetrahydrofuran / 0.5 h / 20 °C
11.1: 93 percent / pyridine; DMAP / 30 h / 50 °C
12.1: TFA; anisole / CH2Cl2 / 9 h / 20 °C
13.1: 19.7 g / ethyl acetate / 1 h / Heating
14.1: 91 percent / TEA / CH2Cl2 / 1 h / 0 °C
15.1: 97 percent / DMAP / acetonitrile / 6.5 h / 20 °C
16.1: NaBH4; H2SO4 / ethanol; CH2Cl2 / 0 °C
17.1: 3.54 g / CSA; quinoline / toluene / 3 h / Heating
18.1: 83 percent / tris(dibenzylideneacetone)dipalladium(0); tris(o-tolyl)phosphine; TEA / acetonitrile / 2 h / Heating
19.1: aq. NaOH / methanol / 2.5 h / Heating
20.1: 106 mg / pyridine; DMAP / CH2Cl2 / 20 °C
21.1: TFA / CH2Cl2 / 4 h / 20 °C
22.1: 2.08 g / NaHCO3 / CH2Cl2; H2O / 0.17 h / 0 °C
23.1: dimethyldioxirane / methanol; acetone / 2 h / 0 °C
24.1: 652 mg / CSA / acetone / 0 - 20 °C
25.1: 94 percent / sodium cyanoborohydride; TFA / tetrahydrofuran / 0.5 h / 0 °C
26.1: 92 percent / imidazole / dimethylformamide / 2 h / 20 °C
27.1: 85 percent / guanidinium nitrate; NaOMe / methanol; CH2Cl2 / 2.5 h / 40 °C
28.1: 91 percent / K2CO3 / acetonitrile / 1 h / Heating
29.1: 82 percent / Red-Al / tetrahydrofuran; toluene / 0 °C
30.1: 73 percent / BF3*OEt2 / CH2Cl2 / 0 °C
31.1: 92 percent / pyridine; DMAP / 20 °C
32.1: 100 percent / aq. HF / acetonitrile / 3 h / 20 °C
33.1: 92 percent / Dess-Martin periodinane / CH2Cl2 / 0.67 h / 20 °C
34.1: 84 percent / H2 / Pd/C / tetrahydrofuran / 18 h / 20 °C / 760.05 Torr
35.1: 89 percent / i-Pr2NEt / CH2Cl2 / 3 h / Heating
36.1: 99 percent / K2CO3 / methanol / 0.5 h / 20 °C
37.1: 94 percent / WSCD*HCl; DMAP / CH2Cl2 / 0.17 h / 20 °C
38.1: 98 percent / hydrazine / acetonitrile / 1.33 h / 20 °C
39.1: TFA / 2,2,2-trifluoro-ethanol / 3 h / 20 °C
40.1: 18.0 mg / pyridine; DMAP / 0.5 h / 20 °C
41.1: 92 percent / Zn; AcOH / diethyl ether / 2.5 h / 20 °C
42.1: 96 percent / AcOH; sodium cyanoborohydride / methanol / 1 h / 20 °C
43.1: 89 percent / Pd(PPh3)2Cl2; AcOH; n-Bu3SnH / CH2Cl2 / 0.33 h / 20 °C
44.1: 4-formyl-1-methylpyridinium benzenesulfonate / dimethylformamide; CH2Cl2 / 0.25 h / 20 °C
44.2: DBU / dimethylformamide; CH2Cl2 / 0.42 h / 20 °C
44.3: 54 percent / aq. citric acid / CH2Cl2; dimethylformamide / 0.67 h / 20 °C
45.1: 96 percent / sodium acetate / ethanol / 5.5 h / 20 °C
46.1: 93 percent / silver nitrate / acetonitrile; H2O / 17 h / 20 °C
View Scheme
Multi-step reaction with 33 steps
1: 1.) BuLi, tetramethylethylene diamine / 1.) hexane, 0 deg C, 4 h, 2.) hexane, from -78 deg C to 23 deg C, 15 min
2: 1.) BuLi / 1.) THF, -30 deg C, 13 h
3: CH3SO3H / CH2Cl2 / 0 °C
4: 1.) NaH / 1.) DMF, 0 deg C, 5 min, 2.) DMF, 23 deg C, 40 min
5: 99 percent / piperidine, acetic acid / benzene / 18 h / 23 °C
6: 94 percent / Et3N, HCOOH, Pd(PPh3)4 / 4 h / 23 °C
7: (PhO)2P(O)N3, Et3N, 4 Angstroem molecular sieves / toluene / 2 h / 70 °C
8: 1 h / 23 °C
9: 97 percent / H2, Rh<(COD)-(R,R)-DIPAMP>(+)*BF4(-) / 16 h / 23 °C / 2280 Torr
10: BF3*Et2O, H2O / CH2Cl2 / 0.17 h / 0 °C
11: BF3*Et2O, 4 Angstroem molecular sieves / CH2Cl2 / 18 h / 23 °C
12: 100 percent / H2 / 10percent Pd/C / ethyl acetate / 6 h / 23 °C / 760 Torr
13: 61 percent / HOAc / 18 h / 23 °C
14: 87 percent / Cs2CO3 / dimethylformamide / 1 h / 23 °C
15: diisobutylaluminum hydride / toluene / 5 h / -78 °C
16: KF*2H2O / methanol / 0.33 h / 23 °C
17: CH3SO3H, 3 Angstroem molecular sieves / CH2Cl2 / 5 h / 23 °C
18: 72 percent / Et3N, DMAP / CH2Cl2 / 6 h / 23 °C
19: 89 percent / DMAP / CH2Cl2 / 13 h / 23 °C
20: 92 percent / i-Pr2NEt / CH2Cl2 / 0.33 h / 23 °C
21: 1.) Bu3SnH, PdCl2(PPh3)2, HOAc, 2.) NaBH3CN, HOAc / 1.) CH2Cl2, 23 deg C, 15 min, 2.) CH3CN, 23 deg C, 30 min
22: 83 percent / PdCl2(PPh3)2, LiCl / dimethylformamide / 2 h / 80 °C
23: (PhSeO)2O / CH2Cl2 / 0.25 h / 23 °C
24: Bu4NF / tetrahydrofuran / 0.17 h / 23 °C
25: 91 percent / 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride, DMAP / CH2Cl2 / 0.5 h / 23 °C
26: 0.5 h / -40 °C
27: 1.) i-Pr2NEt, 2.) tert-butyl alcohol, N-tert-butyl-N',N',N'',N''-tetramethylguanidine / 1.) 0 deg C, 30 min, 2.) 23 deg C
28: 23 °C
29: 84 percent / PdCl2(PPh3)2, Bu3SnH, HOAc / CH2Cl2 / 0.08 h / 23 °C
30: 70 percent / iodide, 1,8-diazabicyclo<6.4.0>undec-7-ene, DMF / CH2Cl2 / 0.67 h / 23 °C
31: 82 percent / silica gel / ethanol / 23 °C
32: aq. CF3COOH / tetrahydrofuran / 9 h / 23 °C
33: aq. AgNO3 / acetonitrile / 11 h / 23 °C
View Scheme
4-hydroxy-5-(methoxymethoxy)-1,3-benzodioxole
244126-41-8

4-hydroxy-5-(methoxymethoxy)-1,3-benzodioxole

ecteinascidin 743
114899-77-3

ecteinascidin 743

Conditions
ConditionsYield
Multi-step reaction with 24 steps
1.1: 97 percent / LiCl; 3 Angstroem molecular sieves / toluene; various solvent(s) / 24 h / 20 °C
2.1: 95 percent / K2CO3 / dimethylformamide / 1 h / 23 °C
3.1: 93 percent / K3PO4; Pd(PPh3)4 / dioxane / 4 h / 100 °C
4.1: 91 percent / benzotriazole; thionyl bromide / CH2Cl2 / 0.33 h / 20 °C
5.1: 68 percent / triethylamine / acetonitrile / 14 h / 0 °C
6.1: 97 percent / imidazole / dimethylformamide / 3 h / 23 °C
7.1: 94 percent / K2CO3; MeOH / 2 h / 23 °C
8.1: Dess-Martin periodinane / CH2Cl2 / 0.33 h / 23 °C
9.1: 1.26 g / ZnCl2 / CH2Cl2; tetrahydrofuran / 0.17 h / 23 °C
10.1: 80 percent / LiBH4 / tetrahydrofuran; methanol / 10 h / 0 °C
11.1: 92 percent / pyridine; DMAP / CH2Cl2 / 0.5 h / 23 °C
12.1: 91 percent / aq. HF / acetonitrile / 2 h / 23 °C
13.1: 93 percent / Dess-Martin periodinane / CH2Cl2 / 0.33 h / 20 °C
14.1: 95 percent / CF3COOH / CH2Cl2 / 0.5 h / 23 °C
15.1: 96 percent / K2CO3; MeOH / 1 h / 20 °C
16.1: 95 percent / DMAP; EDCl / CH2Cl2 / 1 h / 20 °C
17.1: CF3COOH / 2,2,2-trifluoro-ethanol / 3 h / 20 °C
18.1: 143 mg / pyridine; DMAP / CH2Cl2 / 0.5 h / 23 °C
19.1: 87 percent / n-Bu3SnH; AcOH; Pd(PPh3)2Cl2 / CH2Cl2 / 0.33 h / 20 °C
20.1: 97 percent / NaBH3CN; AcOH / acetonitrile; methanol / 2 h / 23 °C
21.1: 92 percent / Zn; AcOH / diethyl ether / 1 h / 23 °C
22.1: 4-formyl-1-methylpyridinium benzenesulfonate / CH2Cl2; dimethylformamide / 0.17 h / 23 °C
22.2: DBU / CH2Cl2; dimethylformamide / 0.25 h / 23 °C
22.3: 53 percent / aq. oxalic acid / CH2Cl2; dimethylformamide / 0.5 h / 23 °C
23.1: 97 percent / NaOAc / ethanol / 3 h / 23 °C
24.1: 92 percent / aq. AgNO3 / acetonitrile / 19 h / 23 °C
View Scheme
Multi-step reaction with 45 steps
1.1: 89 percent / TFA / CH2Cl2 / 2.17 h / -10 °C
2.1: 90 percent / pyridine / CH2Cl2 / 0.08 h / 0 °C
3.1: 85 percent / NaBH4 / methanol / 0.5 h / 0 °C
4.1: 91 percent / imidazole / dimethylformamide / 20 °C
5.1: 97 percent / PdCl2(dppf) / tetrahydrofuran / 4.5 h / Heating
6.1: Pb(OAc)4 / acetonitrile / 0 °C
7.1: 436 mg / NH2OH*HCl; NaOAc / ethanol / 1.5 h / 20 °C
8.1: 90 percent / methanol / 1 h / Heating
9.1: 89 percent / TBAF / tetrahydrofuran / 0.5 h / 20 °C
10.1: 93 percent / pyridine; DMAP / 30 h / 50 °C
11.1: TFA; anisole / CH2Cl2 / 9 h / 20 °C
12.1: 19.7 g / ethyl acetate / 1 h / Heating
13.1: 91 percent / TEA / CH2Cl2 / 1 h / 0 °C
14.1: 97 percent / DMAP / acetonitrile / 6.5 h / 20 °C
15.1: NaBH4; H2SO4 / ethanol; CH2Cl2 / 0 °C
16.1: 3.54 g / CSA; quinoline / toluene / 3 h / Heating
17.1: 83 percent / tris(dibenzylideneacetone)dipalladium(0); tris(o-tolyl)phosphine; TEA / acetonitrile / 2 h / Heating
18.1: aq. NaOH / methanol / 2.5 h / Heating
19.1: 106 mg / pyridine; DMAP / CH2Cl2 / 20 °C
20.1: TFA / CH2Cl2 / 4 h / 20 °C
21.1: 2.08 g / NaHCO3 / CH2Cl2; H2O / 0.17 h / 0 °C
22.1: dimethyldioxirane / methanol; acetone / 2 h / 0 °C
23.1: 652 mg / CSA / acetone / 0 - 20 °C
24.1: 94 percent / sodium cyanoborohydride; TFA / tetrahydrofuran / 0.5 h / 0 °C
25.1: 92 percent / imidazole / dimethylformamide / 2 h / 20 °C
26.1: 85 percent / guanidinium nitrate; NaOMe / methanol; CH2Cl2 / 2.5 h / 40 °C
27.1: 91 percent / K2CO3 / acetonitrile / 1 h / Heating
28.1: 82 percent / Red-Al / tetrahydrofuran; toluene / 0 °C
29.1: 73 percent / BF3*OEt2 / CH2Cl2 / 0 °C
30.1: 92 percent / pyridine; DMAP / 20 °C
31.1: 100 percent / aq. HF / acetonitrile / 3 h / 20 °C
32.1: 92 percent / Dess-Martin periodinane / CH2Cl2 / 0.67 h / 20 °C
33.1: 84 percent / H2 / Pd/C / tetrahydrofuran / 18 h / 20 °C / 760.05 Torr
34.1: 89 percent / i-Pr2NEt / CH2Cl2 / 3 h / Heating
35.1: 99 percent / K2CO3 / methanol / 0.5 h / 20 °C
36.1: 94 percent / WSCD*HCl; DMAP / CH2Cl2 / 0.17 h / 20 °C
37.1: 98 percent / hydrazine / acetonitrile / 1.33 h / 20 °C
38.1: TFA / 2,2,2-trifluoro-ethanol / 3 h / 20 °C
39.1: 18.0 mg / pyridine; DMAP / 0.5 h / 20 °C
40.1: 92 percent / Zn; AcOH / diethyl ether / 2.5 h / 20 °C
41.1: 96 percent / AcOH; sodium cyanoborohydride / methanol / 1 h / 20 °C
42.1: 89 percent / Pd(PPh3)2Cl2; AcOH; n-Bu3SnH / CH2Cl2 / 0.33 h / 20 °C
43.1: 4-formyl-1-methylpyridinium benzenesulfonate / dimethylformamide; CH2Cl2 / 0.25 h / 20 °C
43.2: DBU / dimethylformamide; CH2Cl2 / 0.42 h / 20 °C
43.3: 54 percent / aq. citric acid / CH2Cl2; dimethylformamide / 0.67 h / 20 °C
44.1: 96 percent / sodium acetate / ethanol / 5.5 h / 20 °C
45.1: 93 percent / silver nitrate / acetonitrile; H2O / 17 h / 20 °C
View Scheme
ecteinascidin 743
114899-77-3

ecteinascidin 743

ET-745

ET-745

Conditions
ConditionsYield
With sodium cyanoborohydride; acetic acid In acetonitrile at 23℃; for 0.5h;64%

Ecteinascidin 743 Specification

  Ecteinascidin 743, with cas registry number of 114899-77-3, is a kind of heterocyclic compounds based on its structure. According to its biological activity, it will belong to Antineoplastic agents. Its systematic name is (6R,6aR,7R,13S,14S,16R,20R)-6',8,14-trihydroxy-7',9-dimethoxy-4,10,24-trimethyl-19-oxo-3',4',6,7,12,13,14,16-octahydro-2'H,6aH-spiro[7,13-epimino-6,16-(epithiobutanooxymethano)[1,3]dioxolo[7,8]isoquin o[3,2-b][3]benzazocine-20,1'-isoquinolin]-5-yl acetate . Its brand name is Yondelis . Besides these names, it is also called Trabectedin [INN] ; Trabectedin ; (1'R,6R,6aR,7R,13S,14S,16R)-6',8,14-Trihydroxy-7',9-dimethoxy-4,10,23-trimethyl-19-oxo-3',4',6,7,12,13,14,16-octahydrospiro(6,16-(epithiopropanooxymethano)-7,13-imino-6aH-1,3-dioxolo(7,8)isoquino(3,2-b)(3)benzazocine-20,1'(2'H)-isoquinolin)-5-yl acetate ; CCRIS 8133 ; ET-743 ; Ect 743 ; Ecteinascidine 743 ; Et 743 ; NSC 648766 ; UNII-ID0YZQ2TCP .

 Ecteinascidin 743 is from Alkaloid from the ascidian Ecteinascidia turbinata. It was first determined by KL Rinehart at the University of Illinois in 1984. Ecteinascidin 743 had the anticancer activity. If it was used as a drug, it had to been done the further research in clinical trial. But at that time, the extracted yields were extremely low. Scientists begn to find the synthetic method of Ecteinascidin 743 . In 1996, E. J. Corey and his group developed a method and published it. At the same year, Ecteinascidin 743 was first dosed in humans. Now this product is prepared by a semisynthetic process developed by PharmaMar. The process begins from Safracin B. The antibiotic is obtained by fermentation of the bacterium Pseudomonas fluorescens.

 A lot of toxicity data has been done such as:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
rat LDLo intravenous 75ug/kg (0.075mg/kg) LIVER: OTHER CHANGES
BLOOD: CHANGES IN BONE MARROW NOT INCLUDED ABOVE		 Toxicologist. Vol. 42, Pg. 51, 1998.

  Now Ecteinascidin 743 is very available in the market under the brand name Yondelis provided by Zeltia and Johnson and Johnson. It is approved for the treatment of advanced soft tissue sarcoma in Europe, Russia and South Korea. It is also undergoing clinical trials for the treatment of breast, prostate, and paediatric sarcomas.

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