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Shanghai Upbio Tech Co.,Ltd

1.In No Less 10 years exporting experience. you can 100% received goods 2.Lower Price with higher quality 3,Free sample 4,We are sincerely responsible for the "product quality" and "After Service" Upbio is Specializ

4,12-Dioxa-20-thia-21-azabicyclo[16.2.1]heneicosa-1(21),6,8,18-tetraene-5,13-dione,15-amino-3-[(1E,3E,5E)-7-(dimethylamino)-2,5-dimethyl-1,3,5-heptatrien-1-yl]-9,11,17-trimethyl-,(3S,6Z,8E,11S,15R,17S

Cas:139220-18-1

Min.Order:1 Gram

Negotiable

Type:Lab/Research institutions

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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

4,12-Dioxa-20-thia-21-azabicyclo[16.2.1]heneicosa-1(21),6,8,18-tetraene-5,13-dione,15-amino-3-[(1E,3E,5E)-7-(dimethylamino)-2,5-dimethyl-1,3,5-heptatrien-1-yl]-9,11,17-trimethyl-,(3S,6Z,8E,11S,15R,17S

Cas:139220-18-1

Min.Order:1 Kilogram

Negotiable

Type:Lab/Research institutions

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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

4,12-Dioxa-20-thia-21-azabicyclo[16.2.1]heneicosa-1(21),6,8,18-tetraene-5,13-dione,15-amino-3-[(1E,3E,5E)-7-(dimethylamino)-2,5-dimethyl-1,3,5-heptatrien-1-yl]-9,11,17-trimethyl-,(3S,6Z,8E,11S,15R,17S

Cas:139220-18-1

Min.Order:0

Negotiable

Type:Lab/Research institutions

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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

4,12-Dioxa-20-thia-21-azabicyclo[16.2.1]heneicosa-1(21),6,8,18-tetraene-5,13-dione,15-amino-3-[(1E,3E,5E)-7-(dimethylamino)-2,5-dimethyl-1,3,5-heptatrien-1-yl]-9,11,17-trimethyl-,(3S,6Z,8E,11S,15R,17S

Cas:139220-18-1

Min.Order:10 Gram

FOB Price: $100.0

Type:Lab/Research institutions

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Hebei Mojin Biotechnology Co.,Ltd

We produce carbomer by our own factory,carbomer 940 is our best seller.It is used for cosmetic and medical.And we also become agent for lubrizol.Our carbomer 940 get high viscosity and good transparency.The price will depond on the market,surely supp

4,12-Dioxa-20-thia-21-azabicyclo[16.2.1]heneicosa-1(21),6,8,18-tetraene-5,13-dione,15-amino-3-[(1E,3E,5E)-7-(dimethylamino)-2,5-dimethyl-1,3,5-heptatrien-1-yl]-9,11,17-trimethyl-,(3S,6Z,8E,11S,15R,17S

Cas:139220-18-1

Min.Order:0

Negotiable

Type:Trading Company

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Xi`an Eastling Biotech Co., Ltd.

high purity lowest priceAppearance:solid or liquid Storage:in sealed air resistant place Package:Foil bag; Drum; Plastic bottle Application:Pharma;Industry;Agricultural Transportation:by sea or air Port:Beijing or Guangzhou

4,12-Dioxa-20-thia-21-azabicyclo[16.2.1]heneicosa-1(21),6,8,18-tetraene-5,13-dione,15-amino-3-[(1E,3E,5E)-7-(dimethylamino)-2,5-dimethyl-1,3,5-heptatrien-1-yl]-9,11,17-trimethyl-,(3S,6Z,8E,11S,15R,17S

Cas:139220-18-1

Min.Order:0

Negotiable

Type:Lab/Research institutions

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Hangzhou J&H Chemical Co., Ltd.

J&H CHEM is one of China's leading providers of integrated fine chemical services including offering, research and development, Custom manufacturing business, as well as other Value-added customer services, for diversified range products of chemicals

4,12-Dioxa-20-thia-21-azabicyclo[16.2.1]heneicosa-1(21),6,8,18-tetraene-5,13-dione,15-amino-3-[(1E,3E,5E)-7-(dimethylamino)-2,5-dimethyl-1,3,5-heptatrien-1-yl]-9,11,17-trimethyl-,(3S,6Z,8E,11S,15R,17S

Cas:139220-18-1

Min.Order:0

Negotiable

Type:Lab/Research institutions

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Henan Tianfu Chemical Co., Ltd.

1.Our services：A.Supply sampleB.The packing also can be according the customers` requirmentC.Any inquiries will be replied within 24 hoursD.we provide Commerical Invoice, Packing List, Bill of loading, COA , Health certificate and Origin certificate.

4,12-Dioxa-20-thia-21-azabicyclo[16.2.1]heneicosa-1(21),6,8,18-tetraene-5,13-dione,15-amino-3-[(1E,3E,5E)-7-(dimethylamino)-2,5-dimethyl-1,3,5-heptatrien-1-yl]-9,11,17-trimethyl-,(3S,6Z,8E,11S,15R,17S

Cas:139220-18-1

Min.Order:0

Negotiable

Type:Lab/Research institutions

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Xian Changyue Biological Technology Co., Ltd.

best seller Application:API

4,12-Dioxa-20-thia-21-azabicyclo[16.2.1]heneicosa-1(21),6,8,18-tetraene-5,13-dione,15-amino-3-[(1E,3E,5E)-7-(dimethylamino)-2,5-dimethyl-1,3,5-heptatrien-1-yl]-9,11,17-trimethyl-,(3S,6Z,8E,11S,15R,17S

Cas:139220-18-1

Min.Order:0

Negotiable

Type:Manufacturers

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Antimex Chemical Limied

Ansciep Chemical is a professional enterprise manufacturing and distributing fine chemicals and speciality chemicals. We have been dedicated to heterocycle compounds and phenyl rings for tens of years. This is our mature product for export. Our quali

4,12-Dioxa-20-thia-21-azabicyclo[16.2.1]heneicosa-1(21),6,8,18-tetraene-5,13-dione,15-amino-3-[(1E,3E,5E)-7-(dimethylamino)-2,5-dimethyl-1,3,5-heptatrien-1-yl]-9,11,17-trimethyl-,(3S,6Z,8E,11S,15R,17S

Cas:139220-18-1

Min.Order:0

Negotiable

Type:Lab/Research institutions

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DB BIOTECH CO., LTD

best seller Application:API

4,12-Dioxa-20-thia-21-azabicyclo[16.2.1]heneicosa-1(21),6,8,18-tetraene-5,13-dione,15-amino-3-[(1E,3E,5E)-7-(dimethylamino)-2,5-dimethyl-1,3,5-heptatrien-1-yl]-9,11,17-trimethyl-,(3S,6Z,8E,11S,15R,17S

Cas:139220-18-1

Min.Order:0

Negotiable

Type:Trading Company

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Henan Kanbei Chemical Co.,LTD

factory?direct?saleAppearance:White powder Storage:Sealed and preserved Package:200/Kilograms Application:healing drugs Transportation:By sea Port:Shanghai/tianjin

4,12-Dioxa-20-thia-21-azabicyclo[16.2.1]heneicosa-1(21),6,8,18-tetraene-5,13-dione,15-amino-3-[(1E,3E,5E)-7-(dimethylamino)-2,5-dimethyl-1,3,5-heptatrien-1-yl]-9,11,17-trimethyl-,(3S,6Z,8E,11S,15R,17S

Cas:139220-18-1

Min.Order:0

Negotiable

Type:Lab/Research institutions

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Hebei Muhuang Technology Co., Ltd

best seller Application:API

4,12-Dioxa-20-thia-21-azabicyclo[16.2.1]heneicosa-1(21),6,8,18-tetraene-5,13-dione,15-amino-3-[(1E,3E,5E)-7-(dimethylamino)-2,5-dimethyl-1,3,5-heptatrien-1-yl]-9,11,17-trimethyl-,(3S,6Z,8E,11S,15R,17S

Cas:139220-18-1

Min.Order:0

Negotiable

Type:Trading Company

inquiry

HuBei Ipure Biotech CO.,ltd

HuBei ipure is a diversified product production and operation enterprise, with API, pharma intermediates, and other fine chemicals as well as R&D and pigments development and sales as one of the large enterprises, with more than 130 acres of pl

4,12-Dioxa-20-thia-21-azabicyclo[16.2.1]heneicosa-1(21),6,8,18-tetraene-5,13-dione,15-amino-3-[(1E,3E,5E)-7-(dimethylamino)-2,5-dimethyl-1,3,5-heptatrien-1-yl]-9,11,17-trimethyl-

Cas:139220-18-1

Min.Order:1 Gram

FOB Price: $1.0

Type:Trading Company

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Chengdu Push Bio-technology Co., Ltd

Chengdu Push Bio-technology Co., Ltd. provides more than 4,000 natural monomeric substances, including approximately 6,000 products at different grades, specifications and purities. We have specialized in the R&D of medicinally active ingredients sta

Pateamine A

Cas:139220-18-1

Min.Order:0

Negotiable

Type:Lab/Research institutions

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Nanjing Raymon Biotech Co., Ltd.

4,12-Dioxa-20-thia-21-azabicyclo[16.2.1]heneicosa-1(21),6,8,18-tetraene-5,13-dione,15-amino-3-[(1E,3E,5E)-7-(dimethylamino)-2,5-dimethyl-1,3,5-heptatrien-1-yl]-9,11,17-trimethyl-,(3S,6Z,8E,11S,15R,17SAppearance:Off white to slight yellow solid Storag

4,12-Dioxa-20-thia-21-azabicyclo[16.2.1]heneicosa-1(21),6,8,18-tetraene-5,13-dione,15-amino-3-[(1E,3E,5E)-7-(dimethylamino)-2,5-dimethyl-1,3,5-heptatrien-1-yl]-9,11,17-trimethyl-,(3S,6Z,8E,11S,15R,17S

Cas:139220-18-1

Min.Order:0

Negotiable

Type:Trading Company

inquiry

Hebei Ruishun Trade Co.,Ltd

Supply top quality products with a reasonable price Application:api

139220-18-1

Cas:139220-18-1

Min.Order:0

Negotiable

Type:Trading Company

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Synthetic route

C36H50Cl3N3O6S
201339-93-7

C36H50Cl3N3O6S

(-)-pateamine
139220-18-1

(-)-pateamine

Conditions
ConditionsYield
With 10% Cd/Pd; ammonium acetate In tetrahydrofuran at 25℃; for 3.5h;78%
With ammonium acetate; 10% Cd/Pd In tetrahydrofuran at 20℃; for 5h; Hydrolysis;73%
With ammonium acetate; Cd/Pd In tetrahydrofuran at 20℃; for 3h;73%
[(6Z,8E)-(3S,11S,15R,17S)-3-(tert-butyldimethylsilanyloxymethyl)-9,11,17-trimethyl-5,13-dioxo-4,12-dioxa-20-thia-21-azabicyclo[16.2.1]heneicosa-1(21),6,8,18-tetraen-15-yl]carbamic acid 2,2,2-trichloro-1,1-dimethyl ester
693790-26-0

[(6Z,8E)-(3S,11S,15R,17S)-3-(tert-butyldimethylsilanyloxymethyl)-9,11,17-trimethyl-5,13-dioxo-4,12-dioxa-20-thia-21-azabicyclo[16.2.1]heneicosa-1(21),6,8,18-tetraen-15-yl]carbamic acid 2,2,2-trichloro-1,1-dimethyl ester

(-)-pateamine
139220-18-1

(-)-pateamine

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: 78 percent / TBAF / tetrahydrofuran / 20 h / 20 °C
2: 70 percent / Dess-Martin periodinane / CH2Cl2 / 3.5 h / 0 - 20 °C
3: 73 percent / benzene / 3 h / Heating
4: 68 percent / CrCl2 / tetrahydrofuran / 1.5 h / 20 °C
5: 73 percent / aq. NH4OAc / Cd/Pd / tetrahydrofuran / 3 h / 20 °C
View Scheme
((6Z,8E)-(3S,11S,15R,17S)-3-formyl-9,11,17-trimethyl-5,13-dioxo-4,12-dioxa-20-thia-21-azabicyclo[16.2.1]heneicosa-1(21),6,8,18-tetraen-15-yl)carbamic acid 2,2,2-trichloro-1,1-dimethyl ester
308240-84-8

((6Z,8E)-(3S,11S,15R,17S)-3-formyl-9,11,17-trimethyl-5,13-dioxo-4,12-dioxa-20-thia-21-azabicyclo[16.2.1]heneicosa-1(21),6,8,18-tetraen-15-yl)carbamic acid 2,2,2-trichloro-1,1-dimethyl ester

(-)-pateamine
139220-18-1

(-)-pateamine

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 73 percent / benzene / 3 h / Heating
2: 68 percent / CrCl2 / tetrahydrofuran / 1.5 h / 20 °C
3: 73 percent / aq. NH4OAc / Cd/Pd / tetrahydrofuran / 3 h / 20 °C
View Scheme
Multi-step reaction with 4 steps
1: 73 percent / 3 h / Heating
2: 68 percent / CrCl2 / tetrahydrofuran / 1.5 h / 20 °C
3: 36 percent / Pd(CH3CN)2Cl2 / dimethylformamide / 6 h / 20 °C
4: 73 percent / NH4OAc / Cd-Pb / tetrahydrofuran / 5 h / 20 °C
View Scheme
((6Z,8E)-(3S,11S,15R,17S)-3-hydroxymethyl-9,11,17-trimethyl-5,13-dioxo-4,12-dioxa-20-thia-21-azabicyclo[16.2.1]heneicosa-1(21),6,8,18-tetraen-15-yl)carbamic acid 2,2,2-trichloro-1,1-dimethyl ester
308240-96-2

((6Z,8E)-(3S,11S,15R,17S)-3-hydroxymethyl-9,11,17-trimethyl-5,13-dioxo-4,12-dioxa-20-thia-21-azabicyclo[16.2.1]heneicosa-1(21),6,8,18-tetraen-15-yl)carbamic acid 2,2,2-trichloro-1,1-dimethyl ester

(-)-pateamine
139220-18-1

(-)-pateamine

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 70 percent / Dess-Martin periodinane / CH2Cl2 / 3.5 h / 0 - 20 °C
2: 73 percent / benzene / 3 h / Heating
3: 68 percent / CrCl2 / tetrahydrofuran / 1.5 h / 20 °C
4: 73 percent / aq. NH4OAc / Cd/Pd / tetrahydrofuran / 3 h / 20 °C
View Scheme
Multi-step reaction with 5 steps
1: 70 percent / Dess-Martin reagent; pyridine / CH2Cl2 / 2 h / 20 °C
2: 73 percent / 3 h / Heating
3: 68 percent / CrCl2 / tetrahydrofuran / 1.5 h / 20 °C
4: 36 percent / Pd(CH3CN)2Cl2 / dimethylformamide / 6 h / 20 °C
5: 73 percent / NH4OAc / Cd-Pb / tetrahydrofuran / 5 h / 20 °C
View Scheme
((6Z,8E)-(3S,11S,15R,17S)-9,11,17-trimethyl-3-((E)-2-methyl-3-oxopropenyl)-5,13-dioxo-4,12-dioxa-20-thia-21-azabicyclo[16.2.1]heneicosa-1(21),6,8,18-tetraen-15-yl)carbamic acid 2,2,2-trichloro-1,1-dimethyl ester
308240-85-9

((6Z,8E)-(3S,11S,15R,17S)-9,11,17-trimethyl-3-((E)-2-methyl-3-oxopropenyl)-5,13-dioxo-4,12-dioxa-20-thia-21-azabicyclo[16.2.1]heneicosa-1(21),6,8,18-tetraen-15-yl)carbamic acid 2,2,2-trichloro-1,1-dimethyl ester

(-)-pateamine
139220-18-1

(-)-pateamine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 68 percent / CrCl2 / tetrahydrofuran / 1.5 h / 20 °C
2: 73 percent / aq. NH4OAc / Cd/Pd / tetrahydrofuran / 3 h / 20 °C
View Scheme
Multi-step reaction with 3 steps
1: 68 percent / CrCl2 / tetrahydrofuran / 1.5 h / 20 °C
2: 36 percent / Pd(CH3CN)2Cl2 / dimethylformamide / 6 h / 20 °C
3: 73 percent / NH4OAc / Cd-Pb / tetrahydrofuran / 5 h / 20 °C
View Scheme
((6Z,8E)-(3S,11S,15R,17S)-3-((1E,3E)-4-iodo-2-methylbuta-1,3-dienyl)-9,11,17-trimethyl-5,13-dioxo-4,12-dioxa-20-thia-21-azabicyclo[16.2.1]heneicosa-1(21),6,8,18-tetraen-15-yl)carbamic acid 2,2,2-trichloro-1,1-dimethyl ester
308240-76-8

((6Z,8E)-(3S,11S,15R,17S)-3-((1E,3E)-4-iodo-2-methylbuta-1,3-dienyl)-9,11,17-trimethyl-5,13-dioxo-4,12-dioxa-20-thia-21-azabicyclo[16.2.1]heneicosa-1(21),6,8,18-tetraen-15-yl)carbamic acid 2,2,2-trichloro-1,1-dimethyl ester

(-)-pateamine
139220-18-1

(-)-pateamine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 73 percent / aq. NH4OAc / Cd/Pd / tetrahydrofuran / 3 h / 20 °C
View Scheme
Multi-step reaction with 2 steps
1: 36 percent / Pd(CH3CN)2Cl2 / dimethylformamide / 6 h / 20 °C
2: 73 percent / NH4OAc / Cd-Pb / tetrahydrofuran / 5 h / 20 °C
View Scheme
(+)-(S)-4-tert-Butyldimethylsilyloxy-3-methyl-2-butanone
308240-90-6

(+)-(S)-4-tert-Butyldimethylsilyloxy-3-methyl-2-butanone

(-)-pateamine
139220-18-1

(-)-pateamine

Conditions
ConditionsYield
Multi-step reaction with 19 steps
1.1: LiHMDS / -78 °C
1.2: 86 percent / TMSCl; Br2
2.1: 2,6-lutidene / CH2Cl2 / 12 h / 20 °C
3.1: (CF3CO)2O; pyridine / CH2Cl2 / 0.5 h / -30 °C
4.1: 92 percent / AcOH / tetrahydrofuran; H2O / 12 h / 20 °C
5.1: Et3N / CH2Cl2 / 1 h / 0 °C
6.1: dimethylsulfoxide / 6 h / 60 °C
7.1: 85 percent / DIBAL / toluene / 2 h / 0 °C
8.1: 64 percent / Ti(OEt)4 / CH2Cl2 / 4 h / 50 °C
9.1: LiHMDS / tetrahydrofuran / 0.17 h / -78 °C
10.1: 95 percent / TFA / methanol / 4 h / 20 °C
11.1: 89 percent / pyridine / CH2Cl2 / 2 h / 0 °C
12.1: 87 percent / DDQ / CH2Cl2; H2O / 2 h / 20 °C
13.1: 2,4,6-trichlorobenzoyl chloride; Et3N; DMAP / toluene / 1 h / -30 °C
13.2: Pd(dba)2; Ph3As / dimethylformamide / 1 h / 55 °C
14.1: 78 percent / TBAF / acetic acid; tetrahydrofuran / 24 h / 20 °C
15.1: 70 percent / Dess-Martin reagent; pyridine / CH2Cl2 / 2 h / 20 °C
16.1: 73 percent / 3 h / Heating
17.1: 68 percent / CrCl2 / tetrahydrofuran / 1.5 h / 20 °C
18.1: 36 percent / Pd(CH3CN)2Cl2 / dimethylformamide / 6 h / 20 °C
19.1: 73 percent / NH4OAc / Cd-Pb / tetrahydrofuran / 5 h / 20 °C
View Scheme
(S)-1-bromo-4-(tert-butyldimethylsilanyloxy)-3-methylbutan-2-one
308240-79-1

(S)-1-bromo-4-(tert-butyldimethylsilanyloxy)-3-methylbutan-2-one

(-)-pateamine
139220-18-1

(-)-pateamine

Conditions
ConditionsYield
Multi-step reaction with 18 steps
1.1: 2,6-lutidene / CH2Cl2 / 12 h / 20 °C
2.1: (CF3CO)2O; pyridine / CH2Cl2 / 0.5 h / -30 °C
3.1: 92 percent / AcOH / tetrahydrofuran; H2O / 12 h / 20 °C
4.1: Et3N / CH2Cl2 / 1 h / 0 °C
5.1: dimethylsulfoxide / 6 h / 60 °C
6.1: 85 percent / DIBAL / toluene / 2 h / 0 °C
7.1: 64 percent / Ti(OEt)4 / CH2Cl2 / 4 h / 50 °C
8.1: LiHMDS / tetrahydrofuran / 0.17 h / -78 °C
9.1: 95 percent / TFA / methanol / 4 h / 20 °C
10.1: 89 percent / pyridine / CH2Cl2 / 2 h / 0 °C
11.1: 87 percent / DDQ / CH2Cl2; H2O / 2 h / 20 °C
12.1: 2,4,6-trichlorobenzoyl chloride; Et3N; DMAP / toluene / 1 h / -30 °C
12.2: Pd(dba)2; Ph3As / dimethylformamide / 1 h / 55 °C
13.1: 78 percent / TBAF / acetic acid; tetrahydrofuran / 24 h / 20 °C
14.1: 70 percent / Dess-Martin reagent; pyridine / CH2Cl2 / 2 h / 20 °C
15.1: 73 percent / 3 h / Heating
16.1: 68 percent / CrCl2 / tetrahydrofuran / 1.5 h / 20 °C
17.1: 36 percent / Pd(CH3CN)2Cl2 / dimethylformamide / 6 h / 20 °C
18.1: 73 percent / NH4OAc / Cd-Pb / tetrahydrofuran / 5 h / 20 °C
View Scheme
(S)-3-{2-[(S)-2-(4-Methoxy-benzyloxy)-3-triisopropylsilanyloxy-propyl]-thiazol-4-yl}-butyraldehyde
308240-93-9

(S)-3-{2-[(S)-2-(4-Methoxy-benzyloxy)-3-triisopropylsilanyloxy-propyl]-thiazol-4-yl}-butyraldehyde

(-)-pateamine
139220-18-1

(-)-pateamine

Conditions
ConditionsYield
Multi-step reaction with 12 steps
1.1: 64 percent / Ti(OEt)4 / CH2Cl2 / 4 h / 50 °C
2.1: LiHMDS / tetrahydrofuran / 0.17 h / -78 °C
3.1: 95 percent / TFA / methanol / 4 h / 20 °C
4.1: 89 percent / pyridine / CH2Cl2 / 2 h / 0 °C
5.1: 87 percent / DDQ / CH2Cl2; H2O / 2 h / 20 °C
6.1: 2,4,6-trichlorobenzoyl chloride; Et3N; DMAP / toluene / 1 h / -30 °C
6.2: Pd(dba)2; Ph3As / dimethylformamide / 1 h / 55 °C
7.1: 78 percent / TBAF / acetic acid; tetrahydrofuran / 24 h / 20 °C
8.1: 70 percent / Dess-Martin reagent; pyridine / CH2Cl2 / 2 h / 20 °C
9.1: 73 percent / 3 h / Heating
10.1: 68 percent / CrCl2 / tetrahydrofuran / 1.5 h / 20 °C
11.1: 36 percent / Pd(CH3CN)2Cl2 / dimethylformamide / 6 h / 20 °C
12.1: 73 percent / NH4OAc / Cd-Pb / tetrahydrofuran / 5 h / 20 °C
View Scheme
(S)-3-{2-[(S)-2-(4-Methoxy-benzyloxy)-3-triisopropylsilanyloxy-propyl]-thiazol-4-yl}-butyronitrile
308240-81-5

(S)-3-{2-[(S)-2-(4-Methoxy-benzyloxy)-3-triisopropylsilanyloxy-propyl]-thiazol-4-yl}-butyronitrile

(-)-pateamine
139220-18-1

(-)-pateamine

Conditions
ConditionsYield
Multi-step reaction with 13 steps
1.1: 85 percent / DIBAL / toluene / 2 h / 0 °C
2.1: 64 percent / Ti(OEt)4 / CH2Cl2 / 4 h / 50 °C
3.1: LiHMDS / tetrahydrofuran / 0.17 h / -78 °C
4.1: 95 percent / TFA / methanol / 4 h / 20 °C
5.1: 89 percent / pyridine / CH2Cl2 / 2 h / 0 °C
6.1: 87 percent / DDQ / CH2Cl2; H2O / 2 h / 20 °C
7.1: 2,4,6-trichlorobenzoyl chloride; Et3N; DMAP / toluene / 1 h / -30 °C
7.2: Pd(dba)2; Ph3As / dimethylformamide / 1 h / 55 °C
8.1: 78 percent / TBAF / acetic acid; tetrahydrofuran / 24 h / 20 °C
9.1: 70 percent / Dess-Martin reagent; pyridine / CH2Cl2 / 2 h / 20 °C
10.1: 73 percent / 3 h / Heating
11.1: 68 percent / CrCl2 / tetrahydrofuran / 1.5 h / 20 °C
12.1: 36 percent / Pd(CH3CN)2Cl2 / dimethylformamide / 6 h / 20 °C
13.1: 73 percent / NH4OAc / Cd-Pb / tetrahydrofuran / 5 h / 20 °C
View Scheme
(R)-2-{2-[(S)-2-(4-Methoxy-benzyloxy)-3-triisopropylsilanyloxy-propyl]-thiazol-4-yl}-propan-1-ol
308240-91-7

(R)-2-{2-[(S)-2-(4-Methoxy-benzyloxy)-3-triisopropylsilanyloxy-propyl]-thiazol-4-yl}-propan-1-ol

(-)-pateamine
139220-18-1

(-)-pateamine

Conditions
ConditionsYield
Multi-step reaction with 15 steps
1.1: Et3N / CH2Cl2 / 1 h / 0 °C
2.1: dimethylsulfoxide / 6 h / 60 °C
3.1: 85 percent / DIBAL / toluene / 2 h / 0 °C
4.1: 64 percent / Ti(OEt)4 / CH2Cl2 / 4 h / 50 °C
5.1: LiHMDS / tetrahydrofuran / 0.17 h / -78 °C
6.1: 95 percent / TFA / methanol / 4 h / 20 °C
7.1: 89 percent / pyridine / CH2Cl2 / 2 h / 0 °C
8.1: 87 percent / DDQ / CH2Cl2; H2O / 2 h / 20 °C
9.1: 2,4,6-trichlorobenzoyl chloride; Et3N; DMAP / toluene / 1 h / -30 °C
9.2: Pd(dba)2; Ph3As / dimethylformamide / 1 h / 55 °C
10.1: 78 percent / TBAF / acetic acid; tetrahydrofuran / 24 h / 20 °C
11.1: 70 percent / Dess-Martin reagent; pyridine / CH2Cl2 / 2 h / 20 °C
12.1: 73 percent / 3 h / Heating
13.1: 68 percent / CrCl2 / tetrahydrofuran / 1.5 h / 20 °C
14.1: 36 percent / Pd(CH3CN)2Cl2 / dimethylformamide / 6 h / 20 °C
15.1: 73 percent / NH4OAc / Cd-Pb / tetrahydrofuran / 5 h / 20 °C
View Scheme
Methanesulfonic acid (R)-2-{2-[(S)-2-(4-methoxy-benzyloxy)-3-triisopropylsilanyloxy-propyl]-thiazol-4-yl}-propyl ester
308240-92-8

Methanesulfonic acid (R)-2-{2-[(S)-2-(4-methoxy-benzyloxy)-3-triisopropylsilanyloxy-propyl]-thiazol-4-yl}-propyl ester

(-)-pateamine
139220-18-1

(-)-pateamine

Conditions
ConditionsYield
Multi-step reaction with 14 steps
1.1: dimethylsulfoxide / 6 h / 60 °C
2.1: 85 percent / DIBAL / toluene / 2 h / 0 °C
3.1: 64 percent / Ti(OEt)4 / CH2Cl2 / 4 h / 50 °C
4.1: LiHMDS / tetrahydrofuran / 0.17 h / -78 °C
5.1: 95 percent / TFA / methanol / 4 h / 20 °C
6.1: 89 percent / pyridine / CH2Cl2 / 2 h / 0 °C
7.1: 87 percent / DDQ / CH2Cl2; H2O / 2 h / 20 °C
8.1: 2,4,6-trichlorobenzoyl chloride; Et3N; DMAP / toluene / 1 h / -30 °C
8.2: Pd(dba)2; Ph3As / dimethylformamide / 1 h / 55 °C
9.1: 78 percent / TBAF / acetic acid; tetrahydrofuran / 24 h / 20 °C
10.1: 70 percent / Dess-Martin reagent; pyridine / CH2Cl2 / 2 h / 20 °C
11.1: 73 percent / 3 h / Heating
12.1: 68 percent / CrCl2 / tetrahydrofuran / 1.5 h / 20 °C
13.1: 36 percent / Pd(CH3CN)2Cl2 / dimethylformamide / 6 h / 20 °C
14.1: 73 percent / NH4OAc / Cd-Pb / tetrahydrofuran / 5 h / 20 °C
View Scheme
4-[(R)-2-(tert-Butyl-dimethyl-silanyloxy)-1-methyl-ethyl]-2-[(S)-2-(4-methoxy-benzyloxy)-3-triisopropylsilanyloxy-propyl]-thiazole
308240-80-4

4-[(R)-2-(tert-Butyl-dimethyl-silanyloxy)-1-methyl-ethyl]-2-[(S)-2-(4-methoxy-benzyloxy)-3-triisopropylsilanyloxy-propyl]-thiazole

(-)-pateamine
139220-18-1

(-)-pateamine

Conditions
ConditionsYield
Multi-step reaction with 16 steps
1.1: 92 percent / AcOH / tetrahydrofuran; H2O / 12 h / 20 °C
2.1: Et3N / CH2Cl2 / 1 h / 0 °C
3.1: dimethylsulfoxide / 6 h / 60 °C
4.1: 85 percent / DIBAL / toluene / 2 h / 0 °C
5.1: 64 percent / Ti(OEt)4 / CH2Cl2 / 4 h / 50 °C
6.1: LiHMDS / tetrahydrofuran / 0.17 h / -78 °C
7.1: 95 percent / TFA / methanol / 4 h / 20 °C
8.1: 89 percent / pyridine / CH2Cl2 / 2 h / 0 °C
9.1: 87 percent / DDQ / CH2Cl2; H2O / 2 h / 20 °C
10.1: 2,4,6-trichlorobenzoyl chloride; Et3N; DMAP / toluene / 1 h / -30 °C
10.2: Pd(dba)2; Ph3As / dimethylformamide / 1 h / 55 °C
11.1: 78 percent / TBAF / acetic acid; tetrahydrofuran / 24 h / 20 °C
12.1: 70 percent / Dess-Martin reagent; pyridine / CH2Cl2 / 2 h / 20 °C
13.1: 73 percent / 3 h / Heating
14.1: 68 percent / CrCl2 / tetrahydrofuran / 1.5 h / 20 °C
15.1: 36 percent / Pd(CH3CN)2Cl2 / dimethylformamide / 6 h / 20 °C
16.1: 73 percent / NH4OAc / Cd-Pb / tetrahydrofuran / 5 h / 20 °C
View Scheme
4-[(S)-2-(tert-Butyl-dimethyl-silanyloxy)-1-methyl-ethyl]-2-[(S)-2-(4-methoxy-benzyloxy)-3-triisopropylsilanyloxy-propyl]-4,5-dihydro-thiazol-4-ol

4-[(S)-2-(tert-Butyl-dimethyl-silanyloxy)-1-methyl-ethyl]-2-[(S)-2-(4-methoxy-benzyloxy)-3-triisopropylsilanyloxy-propyl]-4,5-dihydro-thiazol-4-ol

(-)-pateamine
139220-18-1

(-)-pateamine

Conditions
ConditionsYield
Multi-step reaction with 17 steps
1.1: (CF3CO)2O; pyridine / CH2Cl2 / 0.5 h / -30 °C
2.1: 92 percent / AcOH / tetrahydrofuran; H2O / 12 h / 20 °C
3.1: Et3N / CH2Cl2 / 1 h / 0 °C
4.1: dimethylsulfoxide / 6 h / 60 °C
5.1: 85 percent / DIBAL / toluene / 2 h / 0 °C
6.1: 64 percent / Ti(OEt)4 / CH2Cl2 / 4 h / 50 °C
7.1: LiHMDS / tetrahydrofuran / 0.17 h / -78 °C
8.1: 95 percent / TFA / methanol / 4 h / 20 °C
9.1: 89 percent / pyridine / CH2Cl2 / 2 h / 0 °C
10.1: 87 percent / DDQ / CH2Cl2; H2O / 2 h / 20 °C
11.1: 2,4,6-trichlorobenzoyl chloride; Et3N; DMAP / toluene / 1 h / -30 °C
11.2: Pd(dba)2; Ph3As / dimethylformamide / 1 h / 55 °C
12.1: 78 percent / TBAF / acetic acid; tetrahydrofuran / 24 h / 20 °C
13.1: 70 percent / Dess-Martin reagent; pyridine / CH2Cl2 / 2 h / 20 °C
14.1: 73 percent / 3 h / Heating
15.1: 68 percent / CrCl2 / tetrahydrofuran / 1.5 h / 20 °C
16.1: 36 percent / Pd(CH3CN)2Cl2 / dimethylformamide / 6 h / 20 °C
17.1: 73 percent / NH4OAc / Cd-Pb / tetrahydrofuran / 5 h / 20 °C
View Scheme
4-Methyl-benzenesulfinic acid [(S)-3-{2-[(S)-2-(4-methoxy-benzyloxy)-3-triisopropylsilanyloxy-propyl]-thiazol-4-yl}-but-(E)-ylidene]-amide

4-Methyl-benzenesulfinic acid [(S)-3-{2-[(S)-2-(4-methoxy-benzyloxy)-3-triisopropylsilanyloxy-propyl]-thiazol-4-yl}-but-(E)-ylidene]-amide

(-)-pateamine
139220-18-1

(-)-pateamine

Conditions
ConditionsYield
Multi-step reaction with 11 steps
1.1: LiHMDS / tetrahydrofuran / 0.17 h / -78 °C
2.1: 95 percent / TFA / methanol / 4 h / 20 °C
3.1: 89 percent / pyridine / CH2Cl2 / 2 h / 0 °C
4.1: 87 percent / DDQ / CH2Cl2; H2O / 2 h / 20 °C
5.1: 2,4,6-trichlorobenzoyl chloride; Et3N; DMAP / toluene / 1 h / -30 °C
5.2: Pd(dba)2; Ph3As / dimethylformamide / 1 h / 55 °C
6.1: 78 percent / TBAF / acetic acid; tetrahydrofuran / 24 h / 20 °C
7.1: 70 percent / Dess-Martin reagent; pyridine / CH2Cl2 / 2 h / 20 °C
8.1: 73 percent / 3 h / Heating
9.1: 68 percent / CrCl2 / tetrahydrofuran / 1.5 h / 20 °C
10.1: 36 percent / Pd(CH3CN)2Cl2 / dimethylformamide / 6 h / 20 °C
11.1: 73 percent / NH4OAc / Cd-Pb / tetrahydrofuran / 5 h / 20 °C
View Scheme
(3R,5S)-3-Amino-5-{2-[(S)-2-(4-methoxy-benzyloxy)-3-triisopropylsilanyloxy-propyl]-thiazol-4-yl}-hexanoic acid (E)-(S)-4-iodo-1,3-dimethyl-but-3-enyl ester
308240-94-0

(3R,5S)-3-Amino-5-{2-[(S)-2-(4-methoxy-benzyloxy)-3-triisopropylsilanyloxy-propyl]-thiazol-4-yl}-hexanoic acid (E)-(S)-4-iodo-1,3-dimethyl-but-3-enyl ester

(-)-pateamine
139220-18-1

(-)-pateamine

Conditions
ConditionsYield
Multi-step reaction with 9 steps
1.1: 89 percent / pyridine / CH2Cl2 / 2 h / 0 °C
2.1: 87 percent / DDQ / CH2Cl2; H2O / 2 h / 20 °C
3.1: 2,4,6-trichlorobenzoyl chloride; Et3N; DMAP / toluene / 1 h / -30 °C
3.2: Pd(dba)2; Ph3As / dimethylformamide / 1 h / 55 °C
4.1: 78 percent / TBAF / acetic acid; tetrahydrofuran / 24 h / 20 °C
5.1: 70 percent / Dess-Martin reagent; pyridine / CH2Cl2 / 2 h / 20 °C
6.1: 73 percent / 3 h / Heating
7.1: 68 percent / CrCl2 / tetrahydrofuran / 1.5 h / 20 °C
8.1: 36 percent / Pd(CH3CN)2Cl2 / dimethylformamide / 6 h / 20 °C
9.1: 73 percent / NH4OAc / Cd-Pb / tetrahydrofuran / 5 h / 20 °C
View Scheme
(3R,5S)-5-[2-((S)-2-Hydroxy-3-triisopropylsilanyloxy-propyl)-thiazol-4-yl]-3-(2,2,2-trichloro-1,1-dimethyl-ethoxycarbonylamino)-hexanoic acid (E)-(S)-4-iodo-1,3-dimethyl-but-3-enyl ester
308240-83-7

(3R,5S)-5-[2-((S)-2-Hydroxy-3-triisopropylsilanyloxy-propyl)-thiazol-4-yl]-3-(2,2,2-trichloro-1,1-dimethyl-ethoxycarbonylamino)-hexanoic acid (E)-(S)-4-iodo-1,3-dimethyl-but-3-enyl ester

(-)-pateamine
139220-18-1

(-)-pateamine

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1.1: 2,4,6-trichlorobenzoyl chloride; Et3N; DMAP / toluene / 1 h / -30 °C
1.2: Pd(dba)2; Ph3As / dimethylformamide / 1 h / 55 °C
2.1: 78 percent / TBAF / acetic acid; tetrahydrofuran / 24 h / 20 °C
3.1: 70 percent / Dess-Martin reagent; pyridine / CH2Cl2 / 2 h / 20 °C
4.1: 73 percent / 3 h / Heating
5.1: 68 percent / CrCl2 / tetrahydrofuran / 1.5 h / 20 °C
6.1: 36 percent / Pd(CH3CN)2Cl2 / dimethylformamide / 6 h / 20 °C
7.1: 73 percent / NH4OAc / Cd-Pb / tetrahydrofuran / 5 h / 20 °C
View Scheme
((6Z,8E)-(3S,11S,15R,17S)-9,11,17-Trimethyl-5,13-dioxo-3-triisopropylsilanyloxymethyl-4,12-dioxa-20-thia-21-aza-bicyclo[16.2.1]henicosa-1(21),6,8,18-tetraen-15-yl)-carbamic acid 2,2,2-trichloro-1,1-dimethyl-ethyl ester
308240-75-7

((6Z,8E)-(3S,11S,15R,17S)-9,11,17-Trimethyl-5,13-dioxo-3-triisopropylsilanyloxymethyl-4,12-dioxa-20-thia-21-aza-bicyclo[16.2.1]henicosa-1(21),6,8,18-tetraen-15-yl)-carbamic acid 2,2,2-trichloro-1,1-dimethyl-ethyl ester

(-)-pateamine
139220-18-1

(-)-pateamine

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: 78 percent / TBAF / acetic acid; tetrahydrofuran / 24 h / 20 °C
2: 70 percent / Dess-Martin reagent; pyridine / CH2Cl2 / 2 h / 20 °C
3: 73 percent / 3 h / Heating
4: 68 percent / CrCl2 / tetrahydrofuran / 1.5 h / 20 °C
5: 36 percent / Pd(CH3CN)2Cl2 / dimethylformamide / 6 h / 20 °C
6: 73 percent / NH4OAc / Cd-Pb / tetrahydrofuran / 5 h / 20 °C
View Scheme
(3R,5S)-5-{2-[(S)-2-(4-Methoxy-benzyloxy)-3-triisopropylsilanyloxy-propyl]-thiazol-4-yl}-3-((R)-toluene-4-sulfinylamino)-hexanoic acid (E)-(S)-4-iodo-1,3-dimethyl-but-3-enyl ester
308240-82-6

(3R,5S)-5-{2-[(S)-2-(4-Methoxy-benzyloxy)-3-triisopropylsilanyloxy-propyl]-thiazol-4-yl}-3-((R)-toluene-4-sulfinylamino)-hexanoic acid (E)-(S)-4-iodo-1,3-dimethyl-but-3-enyl ester

(-)-pateamine
139220-18-1

(-)-pateamine

Conditions
ConditionsYield
Multi-step reaction with 10 steps
1.1: 95 percent / TFA / methanol / 4 h / 20 °C
2.1: 89 percent / pyridine / CH2Cl2 / 2 h / 0 °C
3.1: 87 percent / DDQ / CH2Cl2; H2O / 2 h / 20 °C
4.1: 2,4,6-trichlorobenzoyl chloride; Et3N; DMAP / toluene / 1 h / -30 °C
4.2: Pd(dba)2; Ph3As / dimethylformamide / 1 h / 55 °C
5.1: 78 percent / TBAF / acetic acid; tetrahydrofuran / 24 h / 20 °C
6.1: 70 percent / Dess-Martin reagent; pyridine / CH2Cl2 / 2 h / 20 °C
7.1: 73 percent / 3 h / Heating
8.1: 68 percent / CrCl2 / tetrahydrofuran / 1.5 h / 20 °C
9.1: 36 percent / Pd(CH3CN)2Cl2 / dimethylformamide / 6 h / 20 °C
10.1: 73 percent / NH4OAc / Cd-Pb / tetrahydrofuran / 5 h / 20 °C
View Scheme
(3R,5S)-5-{2-[(S)-2-(4-Methoxy-benzyloxy)-3-triisopropylsilanyloxy-propyl]-thiazol-4-yl}-3-(2,2,2-trichloro-1,1-dimethyl-ethoxycarbonylamino)-hexanoic acid (E)-(S)-4-iodo-1,3-dimethyl-but-3-enyl ester
308240-95-1

(3R,5S)-5-{2-[(S)-2-(4-Methoxy-benzyloxy)-3-triisopropylsilanyloxy-propyl]-thiazol-4-yl}-3-(2,2,2-trichloro-1,1-dimethyl-ethoxycarbonylamino)-hexanoic acid (E)-(S)-4-iodo-1,3-dimethyl-but-3-enyl ester

(-)-pateamine
139220-18-1

(-)-pateamine

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1.1: 87 percent / DDQ / CH2Cl2; H2O / 2 h / 20 °C
2.1: 2,4,6-trichlorobenzoyl chloride; Et3N; DMAP / toluene / 1 h / -30 °C
2.2: Pd(dba)2; Ph3As / dimethylformamide / 1 h / 55 °C
3.1: 78 percent / TBAF / acetic acid; tetrahydrofuran / 24 h / 20 °C
4.1: 70 percent / Dess-Martin reagent; pyridine / CH2Cl2 / 2 h / 20 °C
5.1: 73 percent / 3 h / Heating
6.1: 68 percent / CrCl2 / tetrahydrofuran / 1.5 h / 20 °C
7.1: 36 percent / Pd(CH3CN)2Cl2 / dimethylformamide / 6 h / 20 °C
8.1: 73 percent / NH4OAc / Cd-Pb / tetrahydrofuran / 5 h / 20 °C
View Scheme
tert-Butyl-((E)-(S)-4-iodo-1,3-dimethyl-but-3-enyloxy)-dimethyl-silane
218782-56-0

tert-Butyl-((E)-(S)-4-iodo-1,3-dimethyl-but-3-enyloxy)-dimethyl-silane

(-)-pateamine
139220-18-1

(-)-pateamine

Conditions
ConditionsYield
Multi-step reaction with 9 steps
1: 94 percent / Pd(PPh3)4, CuI, n-PrNH2 / benzene / 20 h / 25 °C
2: 1.) (COCl)2, DMSO, 2.) Et3N / 1.) CH2Cl2, -78 deg C, 20 min, 2.) CH2Cl2, -78 deg C, 20 min
3: 61 percent / H2O2, NaH2PO4, NaClO2 / acetonitrile; 2-methyl-propan-2-ol / 2.5 h / 0 °C
4: 57 percent / DIAD, Ph3P / tetrahydrofuran / 1.5 h / -20 °C
5: 78 percent / HF, pyridine / tetrahydrofuran / 5 h / 25 °C
6: 68 percent / Et4NCN / CH2Cl2 / 6 h / 25 °C
7: H2 / Pd/CaCO3 poisoned with Pb / methanol / 17 h / 25 °C / 760 Torr
8: 27 percent / Pd2dba3*CHCl3, triphenyl arsine / tetrahydrofuran / 33 h / 25 °C
9: 78 percent / NH4OAc, Cd-Pb / tetrahydrofuran / 3.5 h / 25 °C
View Scheme
(E)-(S)-7-(tert-Butyl-dimethyl-silanyloxy)-5-methyl-oct-4-en-2-yn-1-ol
218782-58-2

(E)-(S)-7-(tert-Butyl-dimethyl-silanyloxy)-5-methyl-oct-4-en-2-yn-1-ol

(-)-pateamine
139220-18-1

(-)-pateamine

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1: 1.) (COCl)2, DMSO, 2.) Et3N / 1.) CH2Cl2, -78 deg C, 20 min, 2.) CH2Cl2, -78 deg C, 20 min
2: 61 percent / H2O2, NaH2PO4, NaClO2 / acetonitrile; 2-methyl-propan-2-ol / 2.5 h / 0 °C
3: 57 percent / DIAD, Ph3P / tetrahydrofuran / 1.5 h / -20 °C
4: 78 percent / HF, pyridine / tetrahydrofuran / 5 h / 25 °C
5: 68 percent / Et4NCN / CH2Cl2 / 6 h / 25 °C
6: H2 / Pd/CaCO3 poisoned with Pb / methanol / 17 h / 25 °C / 760 Torr
7: 27 percent / Pd2dba3*CHCl3, triphenyl arsine / tetrahydrofuran / 33 h / 25 °C
8: 78 percent / NH4OAc, Cd-Pb / tetrahydrofuran / 3.5 h / 25 °C
View Scheme
(E)-(S)-7-(tert-Butyl-dimethyl-silanyloxy)-5-methyl-oct-4-en-2-ynal
218782-60-6

(E)-(S)-7-(tert-Butyl-dimethyl-silanyloxy)-5-methyl-oct-4-en-2-ynal

(-)-pateamine
139220-18-1

(-)-pateamine

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1: 61 percent / H2O2, NaH2PO4, NaClO2 / acetonitrile; 2-methyl-propan-2-ol / 2.5 h / 0 °C
2: 57 percent / DIAD, Ph3P / tetrahydrofuran / 1.5 h / -20 °C
3: 78 percent / HF, pyridine / tetrahydrofuran / 5 h / 25 °C
4: 68 percent / Et4NCN / CH2Cl2 / 6 h / 25 °C
5: H2 / Pd/CaCO3 poisoned with Pb / methanol / 17 h / 25 °C / 760 Torr
6: 27 percent / Pd2dba3*CHCl3, triphenyl arsine / tetrahydrofuran / 33 h / 25 °C
7: 78 percent / NH4OAc, Cd-Pb / tetrahydrofuran / 3.5 h / 25 °C
View Scheme
(E)-(S)-7-(tert-Butyl-dimethyl-silanyloxy)-5-methyl-oct-4-en-2-ynoic acid
201339-95-9

(E)-(S)-7-(tert-Butyl-dimethyl-silanyloxy)-5-methyl-oct-4-en-2-ynoic acid

(-)-pateamine
139220-18-1

(-)-pateamine

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: 57 percent / DIAD, Ph3P / tetrahydrofuran / 1.5 h / -20 °C
2: 78 percent / HF, pyridine / tetrahydrofuran / 5 h / 25 °C
3: 68 percent / Et4NCN / CH2Cl2 / 6 h / 25 °C
4: H2 / Pd/CaCO3 poisoned with Pb / methanol / 17 h / 25 °C / 760 Torr
5: 27 percent / Pd2dba3*CHCl3, triphenyl arsine / tetrahydrofuran / 33 h / 25 °C
6: 78 percent / NH4OAc, Cd-Pb / tetrahydrofuran / 3.5 h / 25 °C
View Scheme
(E)-(R)-5-Bromo-3-triisopropylsilanyloxy-hex-4-enoic acid amide
201339-99-3

(E)-(R)-5-Bromo-3-triisopropylsilanyloxy-hex-4-enoic acid amide

(-)-pateamine
139220-18-1

(-)-pateamine

Conditions
ConditionsYield
Multi-step reaction with 20 steps
1: 72 percent / (PhOPh)2P2S4 / tetrahydrofuran / 0.5 h / 25 °C
2: KHCO3 / 1,2-dimethoxy-ethane / -30 - 25 °C
3: trifluoroacetic anhydride, 2,6-lutidine / 1,2-dimethoxy-ethane / 1 h / -30 °C
4: 80 percent / DIBAL-H / CH2Cl2 / 3 h / -90 °C
5: 1.) NaHMDS / 1.) THF, 25 deg C, 15 min, 2.) THF, 25 deg C, 1.5 h
6: 1.) CuBr*DMS / 1.) THF, Et2O, from -78 to 0 deg C, 30 min, 2.) THF, Et2O, CH2Cl2, -30 deg C, 3.5 h
7: 1.) AlMe3 / 1.) CH2Cl2, toluene, 25 deg C, 30 min, 2.) CH2Cl2, toluene, -20 deg C, 8 h
8: 95 percent / DIBAL-H / tetrahydrofuran; CH2Cl2 / 1.3 h / -78 °C
9: 1.) Sn(OTf)2, N-ethylpiperidine / 1.) CH2Cl2, -50 deg C, 4 h, 2.) CH2Cl2, -78 deg C, 1 h
10: 1.) Et3N / 1.) CH2Cl2, 25 deg C, 30 min, 2.) CH2Cl2, RT, 27 h
11: 92 percent / diisopropylazodicarboxylate, Ph3P / tetrahydrofuran / 2.5 h / 25 °C
12: 96 percent / aq. SmI2 / tetrahydrofuran / 1 h / 0 °C
13: 51 percent / Et3N, DMAP / CH2Cl2 / 12 h / 25 °C
14: 78 percent / TBAF, AcOH / tetrahydrofuran / 1 h / -20 °C
15: 57 percent / DIAD, Ph3P / tetrahydrofuran / 1.5 h / -20 °C
16: 78 percent / HF, pyridine / tetrahydrofuran / 5 h / 25 °C
17: 68 percent / Et4NCN / CH2Cl2 / 6 h / 25 °C
18: H2 / Pd/CaCO3 poisoned with Pb / methanol / 17 h / 25 °C / 760 Torr
19: 27 percent / Pd2dba3*CHCl3, triphenyl arsine / tetrahydrofuran / 33 h / 25 °C
20: 78 percent / NH4OAc, Cd-Pb / tetrahydrofuran / 3.5 h / 25 °C
View Scheme
(E)-(R)-5-Bromo-3-triisopropylsilanyloxy-hex-4-enethioic acid amide
218782-66-2

(E)-(R)-5-Bromo-3-triisopropylsilanyloxy-hex-4-enethioic acid amide

(-)-pateamine
139220-18-1

(-)-pateamine

Conditions
ConditionsYield
Multi-step reaction with 19 steps
1: KHCO3 / 1,2-dimethoxy-ethane / -30 - 25 °C
2: trifluoroacetic anhydride, 2,6-lutidine / 1,2-dimethoxy-ethane / 1 h / -30 °C
3: 80 percent / DIBAL-H / CH2Cl2 / 3 h / -90 °C
4: 1.) NaHMDS / 1.) THF, 25 deg C, 15 min, 2.) THF, 25 deg C, 1.5 h
5: 1.) CuBr*DMS / 1.) THF, Et2O, from -78 to 0 deg C, 30 min, 2.) THF, Et2O, CH2Cl2, -30 deg C, 3.5 h
6: 1.) AlMe3 / 1.) CH2Cl2, toluene, 25 deg C, 30 min, 2.) CH2Cl2, toluene, -20 deg C, 8 h
7: 95 percent / DIBAL-H / tetrahydrofuran; CH2Cl2 / 1.3 h / -78 °C
8: 1.) Sn(OTf)2, N-ethylpiperidine / 1.) CH2Cl2, -50 deg C, 4 h, 2.) CH2Cl2, -78 deg C, 1 h
9: 1.) Et3N / 1.) CH2Cl2, 25 deg C, 30 min, 2.) CH2Cl2, RT, 27 h
10: 92 percent / diisopropylazodicarboxylate, Ph3P / tetrahydrofuran / 2.5 h / 25 °C
11: 96 percent / aq. SmI2 / tetrahydrofuran / 1 h / 0 °C
12: 51 percent / Et3N, DMAP / CH2Cl2 / 12 h / 25 °C
13: 78 percent / TBAF, AcOH / tetrahydrofuran / 1 h / -20 °C
14: 57 percent / DIAD, Ph3P / tetrahydrofuran / 1.5 h / -20 °C
15: 78 percent / HF, pyridine / tetrahydrofuran / 5 h / 25 °C
16: 68 percent / Et4NCN / CH2Cl2 / 6 h / 25 °C
17: H2 / Pd/CaCO3 poisoned with Pb / methanol / 17 h / 25 °C / 760 Torr
18: 27 percent / Pd2dba3*CHCl3, triphenyl arsine / tetrahydrofuran / 33 h / 25 °C
19: 78 percent / NH4OAc, Cd-Pb / tetrahydrofuran / 3.5 h / 25 °C
View Scheme
(E)-(R)-5-Bromo-3-hydroxy-1-((S)-4-isopropyl-2-thioxo-thiazolidin-3-yl)-hex-4-en-1-one
218782-63-9

(E)-(R)-5-Bromo-3-hydroxy-1-((S)-4-isopropyl-2-thioxo-thiazolidin-3-yl)-hex-4-en-1-one

(-)-pateamine
139220-18-1

(-)-pateamine

Conditions
ConditionsYield
Multi-step reaction with 22 steps
1: 99 percent / 2,6-lutidine / CH2Cl2 / 0.67 h / 0 - 20 °C
2: 90 percent / NH3 gas / CH2Cl2 / 0 °C
3: 72 percent / (PhOPh)2P2S4 / tetrahydrofuran / 0.5 h / 25 °C
4: KHCO3 / 1,2-dimethoxy-ethane / -30 - 25 °C
5: trifluoroacetic anhydride, 2,6-lutidine / 1,2-dimethoxy-ethane / 1 h / -30 °C
6: 80 percent / DIBAL-H / CH2Cl2 / 3 h / -90 °C
7: 1.) NaHMDS / 1.) THF, 25 deg C, 15 min, 2.) THF, 25 deg C, 1.5 h
8: 1.) CuBr*DMS / 1.) THF, Et2O, from -78 to 0 deg C, 30 min, 2.) THF, Et2O, CH2Cl2, -30 deg C, 3.5 h
9: 1.) AlMe3 / 1.) CH2Cl2, toluene, 25 deg C, 30 min, 2.) CH2Cl2, toluene, -20 deg C, 8 h
10: 95 percent / DIBAL-H / tetrahydrofuran; CH2Cl2 / 1.3 h / -78 °C
11: 1.) Sn(OTf)2, N-ethylpiperidine / 1.) CH2Cl2, -50 deg C, 4 h, 2.) CH2Cl2, -78 deg C, 1 h
12: 1.) Et3N / 1.) CH2Cl2, 25 deg C, 30 min, 2.) CH2Cl2, RT, 27 h
13: 92 percent / diisopropylazodicarboxylate, Ph3P / tetrahydrofuran / 2.5 h / 25 °C
14: 96 percent / aq. SmI2 / tetrahydrofuran / 1 h / 0 °C
15: 51 percent / Et3N, DMAP / CH2Cl2 / 12 h / 25 °C
16: 78 percent / TBAF, AcOH / tetrahydrofuran / 1 h / -20 °C
17: 57 percent / DIAD, Ph3P / tetrahydrofuran / 1.5 h / -20 °C
18: 78 percent / HF, pyridine / tetrahydrofuran / 5 h / 25 °C
19: 68 percent / Et4NCN / CH2Cl2 / 6 h / 25 °C
20: H2 / Pd/CaCO3 poisoned with Pb / methanol / 17 h / 25 °C / 760 Torr
21: 27 percent / Pd2dba3*CHCl3, triphenyl arsine / tetrahydrofuran / 33 h / 25 °C
22: 78 percent / NH4OAc, Cd-Pb / tetrahydrofuran / 3.5 h / 25 °C
View Scheme
2-((E)-(R)-4-Bromo-2-triisopropylsilanyloxy-pent-3-enyl)-thiazole-4-carbaldehyde
201340-01-4

2-((E)-(R)-4-Bromo-2-triisopropylsilanyloxy-pent-3-enyl)-thiazole-4-carbaldehyde

(-)-pateamine
139220-18-1

(-)-pateamine

Conditions
ConditionsYield
Multi-step reaction with 16 steps
1: 1.) NaHMDS / 1.) THF, 25 deg C, 15 min, 2.) THF, 25 deg C, 1.5 h
2: 1.) CuBr*DMS / 1.) THF, Et2O, from -78 to 0 deg C, 30 min, 2.) THF, Et2O, CH2Cl2, -30 deg C, 3.5 h
3: 1.) AlMe3 / 1.) CH2Cl2, toluene, 25 deg C, 30 min, 2.) CH2Cl2, toluene, -20 deg C, 8 h
4: 95 percent / DIBAL-H / tetrahydrofuran; CH2Cl2 / 1.3 h / -78 °C
5: 1.) Sn(OTf)2, N-ethylpiperidine / 1.) CH2Cl2, -50 deg C, 4 h, 2.) CH2Cl2, -78 deg C, 1 h
6: 1.) Et3N / 1.) CH2Cl2, 25 deg C, 30 min, 2.) CH2Cl2, RT, 27 h
7: 92 percent / diisopropylazodicarboxylate, Ph3P / tetrahydrofuran / 2.5 h / 25 °C
8: 96 percent / aq. SmI2 / tetrahydrofuran / 1 h / 0 °C
9: 51 percent / Et3N, DMAP / CH2Cl2 / 12 h / 25 °C
10: 78 percent / TBAF, AcOH / tetrahydrofuran / 1 h / -20 °C
11: 57 percent / DIAD, Ph3P / tetrahydrofuran / 1.5 h / -20 °C
12: 78 percent / HF, pyridine / tetrahydrofuran / 5 h / 25 °C
13: 68 percent / Et4NCN / CH2Cl2 / 6 h / 25 °C
14: H2 / Pd/CaCO3 poisoned with Pb / methanol / 17 h / 25 °C / 760 Torr
15: 27 percent / Pd2dba3*CHCl3, triphenyl arsine / tetrahydrofuran / 33 h / 25 °C
16: 78 percent / NH4OAc, Cd-Pb / tetrahydrofuran / 3.5 h / 25 °C
View Scheme
(S)-3-[2-((E)-(R)-4-Bromo-2-triisopropylsilanyloxy-pent-3-enyl)-thiazol-4-yl]-butyraldehyde
201340-04-7

(S)-3-[2-((E)-(R)-4-Bromo-2-triisopropylsilanyloxy-pent-3-enyl)-thiazol-4-yl]-butyraldehyde

(-)-pateamine
139220-18-1

(-)-pateamine

Conditions
ConditionsYield
Multi-step reaction with 12 steps
1: 1.) Sn(OTf)2, N-ethylpiperidine / 1.) CH2Cl2, -50 deg C, 4 h, 2.) CH2Cl2, -78 deg C, 1 h
2: 1.) Et3N / 1.) CH2Cl2, 25 deg C, 30 min, 2.) CH2Cl2, RT, 27 h
3: 92 percent / diisopropylazodicarboxylate, Ph3P / tetrahydrofuran / 2.5 h / 25 °C
4: 96 percent / aq. SmI2 / tetrahydrofuran / 1 h / 0 °C
5: 51 percent / Et3N, DMAP / CH2Cl2 / 12 h / 25 °C
6: 78 percent / TBAF, AcOH / tetrahydrofuran / 1 h / -20 °C
7: 57 percent / DIAD, Ph3P / tetrahydrofuran / 1.5 h / -20 °C
8: 78 percent / HF, pyridine / tetrahydrofuran / 5 h / 25 °C
9: 68 percent / Et4NCN / CH2Cl2 / 6 h / 25 °C
10: H2 / Pd/CaCO3 poisoned with Pb / methanol / 17 h / 25 °C / 760 Torr
11: 27 percent / Pd2dba3*CHCl3, triphenyl arsine / tetrahydrofuran / 33 h / 25 °C
12: 78 percent / NH4OAc, Cd-Pb / tetrahydrofuran / 3.5 h / 25 °C
View Scheme
2-((E)-(R)-4-Bromo-2-triisopropylsilanyloxy-pent-3-enyl)-thiazole-4-carboxylic acid ethyl ester
201340-00-3

2-((E)-(R)-4-Bromo-2-triisopropylsilanyloxy-pent-3-enyl)-thiazole-4-carboxylic acid ethyl ester

(-)-pateamine
139220-18-1

(-)-pateamine

Conditions
ConditionsYield
Multi-step reaction with 17 steps
1: 80 percent / DIBAL-H / CH2Cl2 / 3 h / -90 °C
2: 1.) NaHMDS / 1.) THF, 25 deg C, 15 min, 2.) THF, 25 deg C, 1.5 h
3: 1.) CuBr*DMS / 1.) THF, Et2O, from -78 to 0 deg C, 30 min, 2.) THF, Et2O, CH2Cl2, -30 deg C, 3.5 h
4: 1.) AlMe3 / 1.) CH2Cl2, toluene, 25 deg C, 30 min, 2.) CH2Cl2, toluene, -20 deg C, 8 h
5: 95 percent / DIBAL-H / tetrahydrofuran; CH2Cl2 / 1.3 h / -78 °C
6: 1.) Sn(OTf)2, N-ethylpiperidine / 1.) CH2Cl2, -50 deg C, 4 h, 2.) CH2Cl2, -78 deg C, 1 h
7: 1.) Et3N / 1.) CH2Cl2, 25 deg C, 30 min, 2.) CH2Cl2, RT, 27 h
8: 92 percent / diisopropylazodicarboxylate, Ph3P / tetrahydrofuran / 2.5 h / 25 °C
9: 96 percent / aq. SmI2 / tetrahydrofuran / 1 h / 0 °C
10: 51 percent / Et3N, DMAP / CH2Cl2 / 12 h / 25 °C
11: 78 percent / TBAF, AcOH / tetrahydrofuran / 1 h / -20 °C
12: 57 percent / DIAD, Ph3P / tetrahydrofuran / 1.5 h / -20 °C
13: 78 percent / HF, pyridine / tetrahydrofuran / 5 h / 25 °C
14: 68 percent / Et4NCN / CH2Cl2 / 6 h / 25 °C
15: H2 / Pd/CaCO3 poisoned with Pb / methanol / 17 h / 25 °C / 760 Torr
16: 27 percent / Pd2dba3*CHCl3, triphenyl arsine / tetrahydrofuran / 33 h / 25 °C
17: 78 percent / NH4OAc, Cd-Pb / tetrahydrofuran / 3.5 h / 25 °C
View Scheme
(-)-pateamine
139220-18-1

(-)-pateamine

Carbonic acid 11-[((8S,9R,10S,11S,13S,14S,16R,17R)-9-fluoro-11,17-dihydroxy-10,13,16-trimethyl-3-oxo-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthrene-17-carbonyl)-amino]-undecyl ester 4-nitro-phenyl ester
218782-88-8

Carbonic acid 11-[((8S,9R,10S,11S,13S,14S,16R,17R)-9-fluoro-11,17-dihydroxy-10,13,16-trimethyl-3-oxo-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthrene-17-carbonyl)-amino]-undecyl ester 4-nitro-phenyl ester

C64H93FN4O10S

C64H93FN4O10S

Conditions
ConditionsYield
With triethylamine In tetrahydrofuran at 25℃; for 18h;64%

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