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Kono Chem Co.,Ltd

English name:Rivastigmine tartrate Molecular formula : C18H28N2O8 Molecular weight : 400.4235 cas: 129101-54-8 Synonyms: SDZ-ENA 713;ENA 713;ENA-713;Rivastigmine hydrogentartrate;UNII-9IY2357JPE;Carbamic acid, ethylme

CAS:123441-03-2 Rivastigmine

Cas:114899-77-3

Min.Order:1 Kilogram

Negotiable

Type:Other

inquiry

Hangzhou JINLAN Pharm-Drugs Technology Co., Ltd

Jinlan Pharm-Drugs Technology Co.,Limited (with its export company Hangzhou Royall Import & Export Co.,Ltd.)is located in Hangzhou, Zhejiang Province. Neighboring Ningbo port, Shanghai port, Hangzhou Xiaoshan Int’l Airport and Shanghai Pu

Trabectedin 114899-77-3 API

Cas:114899-77-3

Min.Order:1 Gram

Negotiable

Type:Manufacturers

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Wuhan Fortuna Chemical Co.,Ltd

Manufacturer supply Trabectedin CAS 114899-77-3 with attractive price Company profile Wuhan Fortuna Chemical Co.,Ltd established in 2006, is a big integrative chemical enterprise being engaged in Pharmaceutical & its intermediates, Food/Feed

Manufacturer supply Trabectedin CAS 114899-77-3 with attractive price

Cas:114899-77-3

Min.Order:10 Kilogram

FOB Price: $10.0

Type:Trading Company

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Dayang Chem (Hangzhou) Co.,Ltd.

Dayangchem’s R&D center can offer custom synthesis according to the contract research and development services for the fine chemicals, pharmaceutical, biotechnique and some of the other chemicals. Near 20 years DayangChem has provided dif

Trabectedin

Cas:114899-77-3

Min.Order:1 Kilogram

FOB Price: $1.0

Type:Lab/Research institutions

inquiry

Chemwill Asia Co., Ltd.

Our main production base is located in Xuzhou industry park. We are certified both to the ISO 9001 and ISO 14001 Standards, have a safety management system in place.Our R&D team masters core technology for process-design of target building block

Trabectedin

Cas:114899-77-3

Min.Order:5 Kiloliter

FOB Price: $1.2 / 5.0

Type:Manufacturers

inquiry

Hebei Nengqian Chemical Import and Export Co., LTD

Our advantages: 1. All inquiries will be replied within 12 hours. 2. Dedication to quality, supply & service. 3. Strictly on selecting raw materials. 4. Reasonable & competitive price, fast lead time. 5. Sample is available for your eva

ecteinascidin 743

Cas:114899-77-3

Min.Order:1 Kilogram

FOB Price: $9.0 / 99.0

Type:Trading Company

inquiry

Zhuozhou Wenxi import and Export Co., Ltd

WITH US,YOUR MONEY IN SAFE,YOUR BUSINESS IN SAFE 1)Quick Response Within 12 hours; 2)Quality Guarantee: All products are strictly tested by our QC, confirmed by QA and approved by third party lab in China, USA, Canada, Germany, UK, Italy, France et

New production CAS 114899-77-3 with best quality

Cas:114899-77-3

Min.Order:1 Kilogram

FOB Price: $139.0 / 210.0

Type:Trading Company

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Hubei Langyou International Trading Co., Ltd

1. Guaranteed purity; 2. Large quantity in stock; 3. Largest manufacturer; 4. Best service after shipment with email; 5. High quality & competitive price; Appearance:White Crystalline Powder Storage:Store in sealed conta

high quality 114899-77-3 ecteinascidin 743 with best price

Cas:114899-77-3

Min.Order:10 Gram

Negotiable

Type:Other

inquiry

HANWAYS CHEMPHARM CO.,LIMITED

Hanways chempharm is a specialized company concentrating on the R&D, production, marketing and technical service of APIs and pharmaceutical intermediates. The marketing department is located in Wuhan. We have two GMP facilities in Hubei Pr

High Quality Trabectedin 114899-77-3 in Stock Fast Delivery Good Supplier

Cas:114899-77-3

Min.Order:1 Kilogram

FOB Price: $200.0 / 400.0

Type:Trading Company

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Qingdao Beluga Import and Export Co., LTD

ecteinascidin 743 CAS:114899-77-3 Qingdao Belugas Import and Export Co., Ltd. is a scientific and technological company integrating research and development, production and trade of chemical intermediates, specializing in high quality organic interm

ecteinascidin 743 CAS:114899-77-3

Cas:114899-77-3

Min.Order:1 Gram

Negotiable

Type:Lab/Research institutions

inquiry

Shandong Hanjiang Chemical Co., Ltd.

Hello, dear friend! I'm Hansen and Allen from China. Welcome to my lookchem mall! The following is a brief introduction of our company's products and services. If you are interested in our products, please contact us by emai

LIDE PHARMACEUTICALS LIMITED

Advantage : LIDE PHARMACEUTICALS LTD. is a mid-small manufacturing-type enterprise, engaged in pharmaceutical intermediates of R&D, custom-made and production, and also involving trading chemicals for export. We have established the R&amp

Henan Wentao Chemical Product Co., Ltd.

Henan Wentao Chemical Product Co.,Ltd is Located in Zhengzhou High-tech Development Zone with import and export license, We passed ISO 9001:2008 as well, Henan Wentao has developed more than 1000 compounds, which are widely used in the fields of prod

Luyunjia Chemistry Xiamen Limited

Quick Details ProName:Trabectedin CasNo:114899-77-3 Molecular Formula:C39H43N3O11S Appearance:white powder Application:pharmaceutics DeliveryTime:10 days PackAge:1g/bottle Port:shanghai ProductionCapacity:50 Gram/Month Purity:99% Storage

lower price! Edoxaban 114899-77-3

Cas:114899-77-3

Min.Order:1 Gram

Negotiable

Type:Lab/Research institutions

inquiry

Taizhou Crene Biotechnology co.ltd

Our company provides one-stop services of research - development - production for a variety of special prouducts. Not only do we make effective use of our strong technological strength, but also establish of cooperative relations with several well-

Trabectedin 114899-77-3

Cas:114899-77-3

Min.Order:100 Milligram

Negotiable

Type:Lab/Research institutions

inquiry

Afine Chemicals Limited

Company Introduction 1. Established in 2005, with two independent business divisions: Fine chemicals division; Pharmaceutical division. 2. Main product: Optical brightener Textile auxiliary Dye stuff Pigments

TRABECTEDIN

Cas:114899-77-3

Min.Order:1 Gram

Negotiable

Type:Lab/Research institutions

inquiry

Shanghai Hope Chem Co., Ltd

1. Product advantages: exquisite appearance and unique functions. 2. Product Advantages: Our products are the best,fast speed ,in large stock 3. High-quality products and thoughtful service are your greatest satisfaction. 4. The product

Trabectedin

Cas:114899-77-3

Min.Order:0

Negotiable

Type:Lab/Research institutions

inquiry

Hangzhou Lingrui Chemical Co.,Ltd.

114899-77-3 ecteinascidin 743 Appearance:white powder Storage:room temperature Package:according to customers' requirements Application:Pharma intermediates Transportation:By air(EMS or EUB or FedEx or TNT ect...) or by sea(FOB or CIF or CNF ect..

114899-77-3 ecteinascidin 743

Cas:114899-77-3

Min.Order:1 Gram

Negotiable

Type:Other

inquiry

Hangzhou J&H Chemical Co., Ltd.

J&H CHEM R&D center can offer custom synthesis according to the contract research and development services for the fine chemicals, pharmaceutical, biotechnique and some of the other chemicals. J&H CHEM has some Manufacturing base in Jia

Zibo Hangyu Biotechnology Development Co., Ltd

Zibo Hangyu Biotechnology Development Co., Ltd is a leading manufacturer and supplier of chemicals in China. We develop produce and distribute high quality pharmaceuticals, intermediates, special chemicals and OLED intermediates and other fine chemi

Trabectedin

Cas:114899-77-3

Min.Order:10 Gram

FOB Price: $100.0

Type:Lab/Research institutions

inquiry

Chemvon Biotechnology Co. Ltd.

Chemvon Biotechnology Co. Ltd., established in the end of 2004, is a high-technology pharmaceutical and fine chemical company in R&D, manufacturing and sales of Trabectedin. With the experience and specialization in technology of asymmetric sy

Trabectedin in China

Cas:114899-77-3

Min.Order:1 Gram

Negotiable

Type:Lab/Research institutions

inquiry

Henan Tianfu Chemical Co., Ltd.

Our company was built in 2009 with an ISO certificate.In the past 5 years, we have grown up as a famous fine chemicals supplier in China and we had established stable business relationships with Samsung,LG,Merck,Thermo Fisher Scientific and so on.O

114899-77-3 ecteinascidin 743

Cas:114899-77-3

Min.Order:1 Metric Ton

Negotiable

Type:Lab/Research institutions

inquiry

Siwei Development Group Ltd.

Product name: Trabectedin CAS No.:114899-77-3 Molecule Formula:C39H43N3O11S Molecule Weight:761.83 Purity: 99.0% Package: 25kg/drum Description:White crystalline powder Manufacture Standards:Enterprise Standard TESTING ITEMS

Best Quality Trabectedin

Cas:114899-77-3

Min.Order:1 Kilogram

Negotiable

Type:Lab/Research institutions

inquiry

Zibo Dorne chemical technology co. LTD

Product Details Grade: pharmaceutical grade Purity:99%+ ProductionCapacity: 1000 Kilogram/Month Scope of use: For scientific research only(The product must be used legally) Our Advantage 1. Best quality with competitive price. 2. Quick shipping,

ecteinascidin 743

Cas:114899-77-3

Min.Order:1 Gram

Negotiable

Type:Lab/Research institutions

inquiry

Xiamen Jenny Chemical Technology Co., Ltd.

GMP standard, high purity, competitive price, in stock 1. Quick Response: within 6 hours after receiving your email. 2. Quality Guarantee: All products are strictly tested by our QC, confirmed by QA, and approved by a third-party lab in China, USA,

ecteinascidin743

Cas:114899-77-3

Min.Order:1 Milligram

Negotiable

Type:Trading Company

inquiry

Hangzhou Huarong Pharm Co., Ltd.

1. ASMF/US DMF is available. 2. GMP is available. Hangzhou Huarong Pharm Co., Ltd. established since 2009 , has been always focusing on supplying products and services to our clients in the field of small molecule drug. Huarong Pharm has bu

Trabectedin DMF GMP Manufacturer Best price USD99/Gram

Cas:114899-77-3

Min.Order:1 Kilogram

FOB Price: $99.0

Type:Lab/Research institutions

inquiry

EAST CHEMSOURCES LIMITED

factory?direct?saleAppearance:White Powder Storage:Store In Dry, Cool And Ventilated Place Package:25kg/drum, also according to the clients requirement Application:It is widely used as a thickener, emulsifier and stabilizer Transportation:By Sea Or B

114899-77-3 ecteinascidin 743

Cas:114899-77-3

Min.Order:1 Kilogram

FOB Price: $18.0 / 20.0

Type:Trading Company

inquiry

Shandong Mopai Biotechnology Co., LTD

Shandong Mopai Biotechnology Co., LTD is a leading manufacturer and supplier of chemicals in China. We develop produce and distribute high quality pharmaceuticals, intermediates, special chemicals and OLED intermediates and other fine chemicals. W

ecteinascidin 743

Cas:114899-77-3

Min.Order:1 Gram

Negotiable

Type:Lab/Research institutions

inquiry

KAISA GROUP INC

1.Applied in food field.it can improve the immune system and prolong life. 2.Appliedin cosmetic field.it can improve the skin care. 3.Applied in pharmaceutical field.it can treat various dieases. 4.Our product quality assurance will make our customer

114899-77-3 ecteinascidin 743

Cas:114899-77-3

Min.Order:1 Metric Ton

FOB Price: $1.5

Type:Trading Company

inquiry

Hangzhou ZeErRui Chemical Co., Ltd.

Product Name: ecteinascidin 743 Assay: 99.0% Cas No.: 114899-77-3 Drugs for unresectable or specific advanced soft tissue sarcomas Appearance:Detailed see specif

trabectedin manufacture

Cas:114899-77-3

Min.Order:1 Milligram

Negotiable

Type:Lab/Research institutions

inquiry

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%

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