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Chengdu Biopurify Phytochemicals Ltd.

Chengdu Biopurify Phytochemicals Ltd. is a leading company in the research, development, manufacture and marketing of High Quality Phytochemicals and Extracts(especially Active Ingredients from Traditional Chinese Medicine,Traditional Chinese Medic

Ingenol

Cas:30220-46-3

Min.Order:0 Metric Ton

Negotiable

Type:Lab/Research institutions

inquiry

Nanjing Spring & Autumn Biological Engineering Co., Ltd.

Nanjing Spring & Autumn Biological Engineering Co., Ltd. Which was founded at 2008, has an R & D team composed very experienced natural products chemists. The company is a high-tech enterprise engaged in functional health care products raw ma

Factory Supply Euphorbia Pekinensis Extract Ingenol

Cas:30220-46-3

Min.Order:1 Kilogram

Negotiable

Type:Lab/Research institutions

inquiry

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. DayangChem can provide different quantities

Ingenol Manufacturer/High quality/Best price/In stock

Cas:30220-46-3

Min.Order:1 Kilogram

FOB Price: $3.0

Type:Lab/Research institutions

inquiry

Simagchem Corporation

Welcome to Simagchem, your partner in China as a premier supply of bulk specialty chemicals for industry and life science. We introduce experienced quality product and exceptional JIT service with instant market intelligence in China to benefit our

High quality Ingenol supplier in China

Cas:30220-46-3

Min.Order:0 Metric Ton

Negotiable

Type:Manufacturers

inquiry

Hebei yanxi chemical co.,LTD.

hebei yanxi chemical co., LTD who registered capital of 10 million yuan, nearly to $2 million, we have a pharmaceutical raw materials factory production of pharmaceutical raw materials, and a reagent r&d center, and we do research and developm

Ingenol CAS NO.30220-46-3

Cas:30220-46-3

Min.Order:1 Metric Ton

FOB Price: $1.0 / 3.0

Type:Manufacturers

inquiry

Xi'an Xszo Chem Co., Ltd.

1. Factory price and high quality must be guaranteed, base on 8 years of production and R&D experience2. Free samples will be provided,ensure specifications and quality are right for customer3. Customers will receive the most professional technical s

High Content Natural Extract Ingenol HACCP manufacturer

Cas:30220-46-3

Min.Order:1 Gram

FOB Price: $0.1

Type:Manufacturers

inquiry

Shanghai Seasonsgreen Chemical Co.,Ltd

Shanghai Seasonsgreen Chemical is a high-tech research and development, production, sale and custom synthesis set in one high-tech chemical products enterprises. Our sales and marketing division is located in Shanghai, serving international pharmaceu

lower price High quality Ingenol

Cas:30220-46-3

Min.Order:1 Kilogram

FOB Price: $1.0

Type:Manufacturers

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

Ingenol

Cas:30220-46-3

Min.Order:5 Kiloliter

FOB Price: $1.2 / 5.0

Type:Manufacturers

inquiry

Henan Tianfu Chemical Co., Ltd.

Product Name: INGENOL Synonyms: 1A,2,5,5A,6,9,10,10A OCTAHYDRO-5,5A,6-TRIHYDROXY4(HYDROXYMETHYL)1,1,7,9-TETRAMETHYL1H-2,8 AMETHANOCYCLOPENTA[A]CYCLOPROPA[E]CYCLODECEN-11 ONE;1 ALPHA,2,5,5 ALPHA,6,9,10,10 AL

INGENOL

Cas:30220-46-3

Min.Order:1 Kilogram

Negotiable

Type:Lab/Research institutions

inquiry

Hebei Nengqian Chemical Import and Export Co., LTD

With our good experience, we offer detailed technical support and advice to assist customers. We communicate closely with customers to establish their quality requirements. Consistent Quality Our plant has strict quality control in each manufacturin

Ingenol

Cas:30220-46-3

Min.Order:1 Kilogram

FOB Price: $1.0 / 10.0

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

Pharmaceutical Grade CAS 30220-46-3 with competitive price

Cas:30220-46-3

Min.Order:1 Kilogram

FOB Price: $139.0 / 210.0

Type:Trading Company

inquiry

Shanghai Upbio Tech Co.,Ltd

1.No Less 8 years exporting experience. Clients 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 Specialized

Baoji Guokang Healthchem co.,ltd

Our company has been in existence for 10 years since its establishment. We have our own unique team. The company integrates independent research and development, production and sales. We have established famous brands at home and abroad. At prese

Ingenol

Cas:30220-46-3

Min.Order:1 Kilogram

FOB Price: $60.0 / 65.0

Type:Trading Company

inquiry

Qingdao Beluga Import and Export Co., LTD

Ingenol CAS:30220-46-3 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 intermediates, st

Ingenol CAS:30220-46-3

Cas:30220-46-3

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

Leader Biochemical Group

PRODUCT DETAILS

China Largest Factory Manufacturer sales Ingenol CAS 30220-46-3

Cas:30220-46-3

Min.Order:500 Kilogram

FOB Price: $1.0 / 2.0

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-

Ingenol 30220-46-3

Cas:30220-46-3

Min.Order:100 Milligram

Negotiable

Type:Lab/Research institutions

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

Ingenol

Cas:30220-46-3

Min.Order:0

Negotiable

Type:Lab/Research institutions

inquiry

Chemsigma International Co.,Ltd.

bulk production superiority 1,high quality with competitive price in china market 2,fast and safe delivery,goods can be sent out immediately after payment. tracking number is available. 3,our products are with mature technical support. 4.

INGENOL

Cas:30220-46-3

Min.Order:1 Kilogram

FOB Price: $2.0 / 3.0

Type:Lab/Research institutions

inquiry

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

High quality Ingenol

Cas:30220-46-3

Min.Order:10 Gram

FOB Price: $100.0

Type:Lab/Research institutions

inquiry

Henan Wentao Chemical Product Co., Ltd.

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 etc. 3) oem/odm available; 4) rea

INGENOLCAS NO.: 30220-46-3

Cas:30220-46-3

Min.Order:1 Kilogram

FOB Price: $4.0

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,

Ingenol

Cas:30220-46-3

Min.Order:1 Milligram

Negotiable

Type:Trading Company

inquiry

Henan Kanbei Chemical Co.,LTD

High quality, competitive price, fast delivery and first-class service we possesses have won the trust and praise of customers. Standard: BP/USP/EP The purity is equal or greater than 99%. As a supplier, we can provide high-quality products. Cle

Ingenol 99%

Cas:30220-46-3

Min.Order:1 Metric Ton

Negotiable

Type:Lab/Research institutions

inquiry

Shanghai Minstar Chemical Co., Ltd

Ingenol Basic information Description Chemical Properties Ingenol mebutate Pharmacokinetics & metabolism Product Name: Ingenol Synonyms: 1A,2,5,5A,6,9,10,10A OCTAHYDRO-5,5A,6-TRIHYDROXY4(HYDROXYMETHYL)1,1,7,9-TETRAMETHYL1H-2,8 AMETHANOCYCLO

Ingenol

Cas:30220-46-3

Min.Order:1 Milligram

Negotiable

Type:Lab/Research institutions

inquiry

Hubei CuiRan Biotechnology Co., Ltd

Hubei CuiRan Biotechnology Co., Ltd is a leading company in the research, development, manufacture and marketing of High Quality Phytochemicals and Extracts(especially Active Ingredients from Traditional Chinese Medicine,Traditional Chinese Medicine)

Ingenol

Cas:30220-46-3

Min.Order:10 Milligram

Negotiable

Type:Lab/Research institutions

inquiry

Hangzhou Huarong Pharm Co., Ltd.

Hangzhou Huarong Pharm Co., Ltd.established since 2006 , has been actively developing specialty products for Finished Dosages, APIs, Intermediates, and Fine chemicals markets in North America, Europe, Korea, Japan, Mid-East and all over the World. Hu

Ingenol

Cas:30220-46-3

Min.Order:0

Negotiable

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

INGENOL

Cas:30220-46-3

Min.Order:1 Gram

Negotiable

Type:Lab/Research institutions

inquiry

SAGECHEM LIMITED

SAGECHEM is a chemical R&D, manufacturing and distribution company in China since 2009, including pharmaceutical intermediates, agrochemical, dyestuff intermediates, organosilicone, API and etc. We also offer a full range of services in custom synthe

SAGECHEM/Ingenol/SAGECHEM/Manufacturer in China

Cas:30220-46-3

Min.Order:0

Negotiable

Type:Lab/Research institutions

inquiry

shanghai Tauto Biotech Co., Ltd

The quality is guaranteed. If you find the product is wrong compared with COA, we promise 100% refund or change product. COA and HPLC will be shipped out with goods. You can also inform your analysis method and we will follow your analysi

Ingenol

Cas:30220-46-3

Min.Order:0 Metric Ton

Negotiable

Type:Manufacturers

inquiry

Win-Win chemical Co.Ltd

Stock products, own laboratoryAppearance:White to off-white powder Package:Grams, Kilograms Application:For R&D Transportation:According to customer request Port:Shanghai

ingenol cas no. 30220-46-3 98%

Cas:30220-46-3

Min.Order:0

Negotiable

Type:Lab/Research institutions

inquiry

Synthetic route

(1aR,2S,5R,5aS,6S,8aS,9R,10aR)-5,5a,6-trihydroxy-1,1,4,7,9-pentamethyl-1a,2,5,5a,6,9,10,10a-octahydro-1H-2,8a-methanocyclopenta[a]cyclopropa[e][10]annulen-11-one
54706-99-9

(1aR,2S,5R,5aS,6S,8aS,9R,10aR)-5,5a,6-trihydroxy-1,1,4,7,9-pentamethyl-1a,2,5,5a,6,9,10,10a-octahydro-1H-2,8a-methanocyclopenta[a]cyclopropa[e][10]annulen-11-one

ingenol
30220-46-3

ingenol

Conditions
ConditionsYield
With selenium(IV) oxide; formic acid In 1,4-dioxane at 80℃; for 1.25h;76%
Stage #1: (1aR,2S,5R,5aS,6S,8aS,9R,10aR)-5,5a,6-trihydroxy-1,1,4,7,9-pentamethyl-1a,2,5,5a,6,9,10,10a-octahydro-1H-2,8a-methanocyclopenta[a]cyclopropa[e][10]annulen-11-one With selenium(IV) oxide; formic acid In 1,4-dioxane at 80℃; for 2h; Inert atmosphere;
Stage #2: With sodium hydroxide In 1,4-dioxane; water for 0.5h; Inert atmosphere;
76%
With selenium(IV) oxide In 1,4-dioxane; formic acid at 80℃; for 2h;70%
With selenium(IV) oxide; silica gel In tetrahydrofuran at 80℃; for 2h;40%
ingenol monoacetate
64280-37-1

ingenol monoacetate

ingenol
30220-46-3

ingenol

Conditions
ConditionsYield
With potassium hydroxide In methanol; water at 0 - 20℃; Temperature; Solvent; Inert atmosphere;74%
ingenol 3,5,20-triacetate
30220-45-2

ingenol 3,5,20-triacetate

ingenol
30220-46-3

ingenol

Conditions
ConditionsYield
With sodium methylate In methanol71%
(6S,6aR,7aR,9R,9aS,12S,12aR,12bR)-12,12a-dihydroxy-2,2,7,7,9,11-hexamethyl-4,6,6a,7,7a,8,9,12,12a,12b-decahydro-6,9a-methanocyclopenta[9,10]cyclopropa[5,6]cyclodeca[1,2-d][1,3]dioxin-13-one
77573-43-4

(6S,6aR,7aR,9R,9aS,12S,12aR,12bR)-12,12a-dihydroxy-2,2,7,7,9,11-hexamethyl-4,6,6a,7,7a,8,9,12,12a,12b-decahydro-6,9a-methanocyclopenta[9,10]cyclopropa[5,6]cyclodeca[1,2-d][1,3]dioxin-13-one

A

ingenol
30220-46-3

ingenol

B

Ingenol-3,4-acetonid

Ingenol-3,4-acetonid

Conditions
ConditionsYield
With perchloric acid In methanol for 1h;A 66%
B n/a
ingenol-3,4:5,20-diacetonide
77573-44-5

ingenol-3,4:5,20-diacetonide

A

ingenol
30220-46-3

ingenol

B

(6S,6aR,7aR,9R,9aS,12S,12aR,12bR)-12,12a-dihydroxy-2,2,7,7,9,11-hexamethyl-4,6,6a,7,7a,8,9,12,12a,12b-decahydro-6,9a-methanocyclopenta[9,10]cyclopropa[5,6]cyclodeca[1,2-d][1,3]dioxin-13-one
77573-43-4

(6S,6aR,7aR,9R,9aS,12S,12aR,12bR)-12,12a-dihydroxy-2,2,7,7,9,11-hexamethyl-4,6,6a,7,7a,8,9,12,12a,12b-decahydro-6,9a-methanocyclopenta[9,10]cyclopropa[5,6]cyclodeca[1,2-d][1,3]dioxin-13-one

C

Ingenol-3,4-acetonid

Ingenol-3,4-acetonid

Conditions
ConditionsYield
With perchloric acid In methanol for 0.75h; Further byproducts given;A 31%
B 3%
C 18%
C43H47N3O9
49620-09-9

C43H47N3O9

ingenol
30220-46-3

ingenol

Conditions
ConditionsYield
With sodium methylate In methanol
ingenol 3-(2,4,6,8,10)-tetradecapentaenoate
42483-56-7

ingenol 3-(2,4,6,8,10)-tetradecapentaenoate

ingenol
30220-46-3

ingenol

Conditions
ConditionsYield
With sodium methylate In methanol
ingenol-3-(t-butyldimethyl)silyl ether

ingenol-3-(t-butyldimethyl)silyl ether

ingenol
30220-46-3

ingenol

Conditions
ConditionsYield
With tetrabutyl ammonium fluoride In tetrahydrofuran for 0.5h;
20-O-Isobutyryl-ingenol

20-O-Isobutyryl-ingenol

ingenol
30220-46-3

ingenol

Conditions
ConditionsYield
With potassium hydroxide In methanol for 0.5h; Yield given;
3-O-Propionyl-20-O-(S)-(2'-methyl)butyryl-ingenol

3-O-Propionyl-20-O-(S)-(2'-methyl)butyryl-ingenol

A

ingenol
30220-46-3

ingenol

B

20-O-(S)-(2'-Methyl)butyryl-ingenol

20-O-(S)-(2'-Methyl)butyryl-ingenol

Conditions
ConditionsYield
With sodium methylate In methanol for 0.666667h; Ambient temperature; Yield given. Yields of byproduct given;
3,4-O-isopropylidene-20-deoxyingenol
91413-76-2

3,4-O-isopropylidene-20-deoxyingenol

ingenol
30220-46-3

ingenol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 92 percent / aq. HCl / tetrahydrofuran / 5 h / 20 °C
2: 40 percent / SeO2/SiO2 / tetrahydrofuran / 2 h / 80 °C
View Scheme
C20H30O3

C20H30O3

ingenol
30220-46-3

ingenol

Conditions
ConditionsYield
Multi-step reaction with 21 steps
1.1: 98 percent / KH / tetrahydrofuran / Heating
2.1: 76 percent / Hoveyda-Grubbs catalyst / toluene / 30 h / Heating
3.1: aq. HCl / tetrahydrofuran / 3 h / Heating
4.1: 1.9 g / NaBH4 / ethanol; tetrahydrofuran / 0.25 h / 0 °C
5.1: PPh3; imidazole; I2 / tetrahydrofuran / 3 h / 0 °C
5.2: 94 percent / t-BuOK / tetrahydrofuran; dimethylsulfoxide / 20 °C
6.1: 49 percent / SeO2; aq. AcOH; t-BuOOH / CH2Cl2; decane / 2 h / 20 °C
7.1: 74 percent / Dess-Martin periodinane / CH2Cl2 / 1.5 h / -40 - 10 °C
8.1: 74 percent / aq. RhCl3 / aq. ethanol / 0.58 h / 115 °C
9.1: 94 percent / P(OMe)3; O2; t-BuOK / tetrahydrofuran; 2-methyl-propan-2-ol / 0.75 h / -40 °C
10.1: 73 percent / VO(acac)2; t-BuOOH / benzene; decane / 10 h / 20 °C
11.1: 72 percent / Et3N / CH2Cl2 / 1 h / -10 - -5 °C
12.1: NaBH4 / methanol / 5 h / 20 °C
13.1: 39 mg / PPTS / CH2Cl2 / 0.5 h / Heating
14.1: 90 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / CH2Cl2 / 18 h / 20 °C
15.1: 96 percent / Et3N / CH2Cl2 / 0.75 h / -78 °C
16.1: 76 percent / Li2CO3 / dimethylformamide / 5 h / 55 °C
17.1: 97 percent / (NH4)6Mo7O24; aq. H2O2 / aq. ethanol / 6 h / 20 °C
18.1: 47 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / benzene / 5 h / Heating
19.1: 76 percent / Na2HPO4; Na(Hg) / methanol / 0.42 h / -20 - -10 °C
20.1: 92 percent / aq. HCl / tetrahydrofuran / 5 h / 20 °C
21.1: 40 percent / SeO2/SiO2 / tetrahydrofuran / 2 h / 80 °C
View Scheme
C23H32O5
827325-49-5

C23H32O5

ingenol
30220-46-3

ingenol

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1: 96 percent / Et3N / CH2Cl2 / 0.75 h / -78 °C
2: 76 percent / Li2CO3 / dimethylformamide / 5 h / 55 °C
3: 97 percent / (NH4)6Mo7O24; aq. H2O2 / aq. ethanol / 6 h / 20 °C
4: 47 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / benzene / 5 h / Heating
5: 76 percent / Na2HPO4; Na(Hg) / methanol / 0.42 h / -20 - -10 °C
6: 92 percent / aq. HCl / tetrahydrofuran / 5 h / 20 °C
7: 40 percent / SeO2/SiO2 / tetrahydrofuran / 2 h / 80 °C
View Scheme
C28H34O4
827325-41-7

C28H34O4

ingenol
30220-46-3

ingenol

Conditions
ConditionsYield
Multi-step reaction with 13 steps
1: 94 percent / P(OMe)3; O2; t-BuOK / tetrahydrofuran; 2-methyl-propan-2-ol / 0.75 h / -40 °C
2: 73 percent / VO(acac)2; t-BuOOH / benzene; decane / 10 h / 20 °C
3: 72 percent / Et3N / CH2Cl2 / 1 h / -10 - -5 °C
4: NaBH4 / methanol / 5 h / 20 °C
5: 39 mg / PPTS / CH2Cl2 / 0.5 h / Heating
6: 90 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / CH2Cl2 / 18 h / 20 °C
7: 96 percent / Et3N / CH2Cl2 / 0.75 h / -78 °C
8: 76 percent / Li2CO3 / dimethylformamide / 5 h / 55 °C
9: 97 percent / (NH4)6Mo7O24; aq. H2O2 / aq. ethanol / 6 h / 20 °C
10: 47 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / benzene / 5 h / Heating
11: 76 percent / Na2HPO4; Na(Hg) / methanol / 0.42 h / -20 - -10 °C
12: 92 percent / aq. HCl / tetrahydrofuran / 5 h / 20 °C
13: 40 percent / SeO2/SiO2 / tetrahydrofuran / 2 h / 80 °C
View Scheme
C28H36O4

C28H36O4

ingenol
30220-46-3

ingenol

Conditions
ConditionsYield
Multi-step reaction with 18 steps
1.1: 1.9 g / NaBH4 / ethanol; tetrahydrofuran / 0.25 h / 0 °C
2.1: PPh3; imidazole; I2 / tetrahydrofuran / 3 h / 0 °C
2.2: 94 percent / t-BuOK / tetrahydrofuran; dimethylsulfoxide / 20 °C
3.1: 49 percent / SeO2; aq. AcOH; t-BuOOH / CH2Cl2; decane / 2 h / 20 °C
4.1: 74 percent / Dess-Martin periodinane / CH2Cl2 / 1.5 h / -40 - 10 °C
5.1: 74 percent / aq. RhCl3 / aq. ethanol / 0.58 h / 115 °C
6.1: 94 percent / P(OMe)3; O2; t-BuOK / tetrahydrofuran; 2-methyl-propan-2-ol / 0.75 h / -40 °C
7.1: 73 percent / VO(acac)2; t-BuOOH / benzene; decane / 10 h / 20 °C
8.1: 72 percent / Et3N / CH2Cl2 / 1 h / -10 - -5 °C
9.1: NaBH4 / methanol / 5 h / 20 °C
10.1: 39 mg / PPTS / CH2Cl2 / 0.5 h / Heating
11.1: 90 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / CH2Cl2 / 18 h / 20 °C
12.1: 96 percent / Et3N / CH2Cl2 / 0.75 h / -78 °C
13.1: 76 percent / Li2CO3 / dimethylformamide / 5 h / 55 °C
14.1: 97 percent / (NH4)6Mo7O24; aq. H2O2 / aq. ethanol / 6 h / 20 °C
15.1: 47 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / benzene / 5 h / Heating
16.1: 76 percent / Na2HPO4; Na(Hg) / methanol / 0.42 h / -20 - -10 °C
17.1: 92 percent / aq. HCl / tetrahydrofuran / 5 h / 20 °C
18.1: 40 percent / SeO2/SiO2 / tetrahydrofuran / 2 h / 80 °C
View Scheme
C24H34O7S
827325-50-8

C24H34O7S

ingenol
30220-46-3

ingenol

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: 76 percent / Li2CO3 / dimethylformamide / 5 h / 55 °C
2: 97 percent / (NH4)6Mo7O24; aq. H2O2 / aq. ethanol / 6 h / 20 °C
3: 47 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / benzene / 5 h / Heating
4: 76 percent / Na2HPO4; Na(Hg) / methanol / 0.42 h / -20 - -10 °C
5: 92 percent / aq. HCl / tetrahydrofuran / 5 h / 20 °C
6: 40 percent / SeO2/SiO2 / tetrahydrofuran / 2 h / 80 °C
View Scheme
C28H36O3
827325-39-3

C28H36O3

ingenol
30220-46-3

ingenol

Conditions
ConditionsYield
Multi-step reaction with 16 steps
1: 49 percent / SeO2; aq. AcOH; t-BuOOH / CH2Cl2; decane / 2 h / 20 °C
2: 74 percent / Dess-Martin periodinane / CH2Cl2 / 1.5 h / -40 - 10 °C
3: 74 percent / aq. RhCl3 / aq. ethanol / 0.58 h / 115 °C
4: 94 percent / P(OMe)3; O2; t-BuOK / tetrahydrofuran; 2-methyl-propan-2-ol / 0.75 h / -40 °C
5: 73 percent / VO(acac)2; t-BuOOH / benzene; decane / 10 h / 20 °C
6: 72 percent / Et3N / CH2Cl2 / 1 h / -10 - -5 °C
7: NaBH4 / methanol / 5 h / 20 °C
8: 39 mg / PPTS / CH2Cl2 / 0.5 h / Heating
9: 90 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / CH2Cl2 / 18 h / 20 °C
10: 96 percent / Et3N / CH2Cl2 / 0.75 h / -78 °C
11: 76 percent / Li2CO3 / dimethylformamide / 5 h / 55 °C
12: 97 percent / (NH4)6Mo7O24; aq. H2O2 / aq. ethanol / 6 h / 20 °C
13: 47 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / benzene / 5 h / Heating
14: 76 percent / Na2HPO4; Na(Hg) / methanol / 0.42 h / -20 - -10 °C
15: 92 percent / aq. HCl / tetrahydrofuran / 5 h / 20 °C
16: 40 percent / SeO2/SiO2 / tetrahydrofuran / 2 h / 80 °C
View Scheme
C28H38O4
827325-56-4

C28H38O4

ingenol
30220-46-3

ingenol

Conditions
ConditionsYield
Multi-step reaction with 17 steps
1.1: PPh3; imidazole; I2 / tetrahydrofuran / 3 h / 0 °C
1.2: 94 percent / t-BuOK / tetrahydrofuran; dimethylsulfoxide / 20 °C
2.1: 49 percent / SeO2; aq. AcOH; t-BuOOH / CH2Cl2; decane / 2 h / 20 °C
3.1: 74 percent / Dess-Martin periodinane / CH2Cl2 / 1.5 h / -40 - 10 °C
4.1: 74 percent / aq. RhCl3 / aq. ethanol / 0.58 h / 115 °C
5.1: 94 percent / P(OMe)3; O2; t-BuOK / tetrahydrofuran; 2-methyl-propan-2-ol / 0.75 h / -40 °C
6.1: 73 percent / VO(acac)2; t-BuOOH / benzene; decane / 10 h / 20 °C
7.1: 72 percent / Et3N / CH2Cl2 / 1 h / -10 - -5 °C
8.1: NaBH4 / methanol / 5 h / 20 °C
9.1: 39 mg / PPTS / CH2Cl2 / 0.5 h / Heating
10.1: 90 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / CH2Cl2 / 18 h / 20 °C
11.1: 96 percent / Et3N / CH2Cl2 / 0.75 h / -78 °C
12.1: 76 percent / Li2CO3 / dimethylformamide / 5 h / 55 °C
13.1: 97 percent / (NH4)6Mo7O24; aq. H2O2 / aq. ethanol / 6 h / 20 °C
14.1: 47 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / benzene / 5 h / Heating
15.1: 76 percent / Na2HPO4; Na(Hg) / methanol / 0.42 h / -20 - -10 °C
16.1: 92 percent / aq. HCl / tetrahydrofuran / 5 h / 20 °C
17.1: 40 percent / SeO2/SiO2 / tetrahydrofuran / 2 h / 80 °C
View Scheme
C28H34O5
827325-42-8

C28H34O5

ingenol
30220-46-3

ingenol

Conditions
ConditionsYield
Multi-step reaction with 12 steps
1: 73 percent / VO(acac)2; t-BuOOH / benzene; decane / 10 h / 20 °C
2: 72 percent / Et3N / CH2Cl2 / 1 h / -10 - -5 °C
3: NaBH4 / methanol / 5 h / 20 °C
4: 39 mg / PPTS / CH2Cl2 / 0.5 h / Heating
5: 90 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / CH2Cl2 / 18 h / 20 °C
6: 96 percent / Et3N / CH2Cl2 / 0.75 h / -78 °C
7: 76 percent / Li2CO3 / dimethylformamide / 5 h / 55 °C
8: 97 percent / (NH4)6Mo7O24; aq. H2O2 / aq. ethanol / 6 h / 20 °C
9: 47 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / benzene / 5 h / Heating
10: 76 percent / Na2HPO4; Na(Hg) / methanol / 0.42 h / -20 - -10 °C
11: 92 percent / aq. HCl / tetrahydrofuran / 5 h / 20 °C
12: 40 percent / SeO2/SiO2 / tetrahydrofuran / 2 h / 80 °C
View Scheme
C29H36O4S
827325-51-9

C29H36O4S

ingenol
30220-46-3

ingenol

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 97 percent / (NH4)6Mo7O24; aq. H2O2 / aq. ethanol / 6 h / 20 °C
2: 47 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / benzene / 5 h / Heating
3: 76 percent / Na2HPO4; Na(Hg) / methanol / 0.42 h / -20 - -10 °C
4: 92 percent / aq. HCl / tetrahydrofuran / 5 h / 20 °C
5: 40 percent / SeO2/SiO2 / tetrahydrofuran / 2 h / 80 °C
View Scheme
C28H36O4
827325-40-6

C28H36O4

ingenol
30220-46-3

ingenol

Conditions
ConditionsYield
Multi-step reaction with 15 steps
1: 74 percent / Dess-Martin periodinane / CH2Cl2 / 1.5 h / -40 - 10 °C
2: 74 percent / aq. RhCl3 / aq. ethanol / 0.58 h / 115 °C
3: 94 percent / P(OMe)3; O2; t-BuOK / tetrahydrofuran; 2-methyl-propan-2-ol / 0.75 h / -40 °C
4: 73 percent / VO(acac)2; t-BuOOH / benzene; decane / 10 h / 20 °C
5: 72 percent / Et3N / CH2Cl2 / 1 h / -10 - -5 °C
6: NaBH4 / methanol / 5 h / 20 °C
7: 39 mg / PPTS / CH2Cl2 / 0.5 h / Heating
8: 90 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / CH2Cl2 / 18 h / 20 °C
9: 96 percent / Et3N / CH2Cl2 / 0.75 h / -78 °C
10: 76 percent / Li2CO3 / dimethylformamide / 5 h / 55 °C
11: 97 percent / (NH4)6Mo7O24; aq. H2O2 / aq. ethanol / 6 h / 20 °C
12: 47 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / benzene / 5 h / Heating
13: 76 percent / Na2HPO4; Na(Hg) / methanol / 0.42 h / -20 - -10 °C
14: 92 percent / aq. HCl / tetrahydrofuran / 5 h / 20 °C
15: 40 percent / SeO2/SiO2 / tetrahydrofuran / 2 h / 80 °C
View Scheme
C28H34O4
827325-57-5

C28H34O4

ingenol
30220-46-3

ingenol

Conditions
ConditionsYield
Multi-step reaction with 14 steps
1: 74 percent / aq. RhCl3 / aq. ethanol / 0.58 h / 115 °C
2: 94 percent / P(OMe)3; O2; t-BuOK / tetrahydrofuran; 2-methyl-propan-2-ol / 0.75 h / -40 °C
3: 73 percent / VO(acac)2; t-BuOOH / benzene; decane / 10 h / 20 °C
4: 72 percent / Et3N / CH2Cl2 / 1 h / -10 - -5 °C
5: NaBH4 / methanol / 5 h / 20 °C
6: 39 mg / PPTS / CH2Cl2 / 0.5 h / Heating
7: 90 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / CH2Cl2 / 18 h / 20 °C
8: 96 percent / Et3N / CH2Cl2 / 0.75 h / -78 °C
9: 76 percent / Li2CO3 / dimethylformamide / 5 h / 55 °C
10: 97 percent / (NH4)6Mo7O24; aq. H2O2 / aq. ethanol / 6 h / 20 °C
11: 47 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / benzene / 5 h / Heating
12: 76 percent / Na2HPO4; Na(Hg) / methanol / 0.42 h / -20 - -10 °C
13: 92 percent / aq. HCl / tetrahydrofuran / 5 h / 20 °C
14: 40 percent / SeO2/SiO2 / tetrahydrofuran / 2 h / 80 °C
View Scheme
C29H36O6S

C29H36O6S

ingenol
30220-46-3

ingenol

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 47 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / benzene / 4 h / Heating
2: 76 percent / Na2HPO4; Na(Hg) / methanol / 0.42 h / -20 - -10 °C
3: 92 percent / aq. HCl / tetrahydrofuran / 5 h / 20 °C
4: 40 percent / SeO2/SiO2 / tetrahydrofuran / 2 h / 80 °C
View Scheme
C29H36O6S
827325-54-2

C29H36O6S

ingenol
30220-46-3

ingenol

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 76 percent / Na2HPO4; Na(Hg) / methanol / 0.42 h / -20 - -10 °C
2: 92 percent / aq. HCl / tetrahydrofuran / 5 h / 20 °C
3: 40 percent / SeO2/SiO2 / tetrahydrofuran / 2 h / 80 °C
View Scheme
C29H36O6S
827325-52-0

C29H36O6S

ingenol
30220-46-3

ingenol

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 47 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / benzene / 5 h / Heating
2: 76 percent / Na2HPO4; Na(Hg) / methanol / 0.42 h / -20 - -10 °C
3: 92 percent / aq. HCl / tetrahydrofuran / 5 h / 20 °C
4: 40 percent / SeO2/SiO2 / tetrahydrofuran / 2 h / 80 °C
View Scheme
C30H40O5
827325-38-2

C30H40O5

ingenol
30220-46-3

ingenol

Conditions
ConditionsYield
Multi-step reaction with 19 steps
1.1: aq. HCl / tetrahydrofuran / 3 h / Heating
2.1: 1.9 g / NaBH4 / ethanol; tetrahydrofuran / 0.25 h / 0 °C
3.1: PPh3; imidazole; I2 / tetrahydrofuran / 3 h / 0 °C
3.2: 94 percent / t-BuOK / tetrahydrofuran; dimethylsulfoxide / 20 °C
4.1: 49 percent / SeO2; aq. AcOH; t-BuOOH / CH2Cl2; decane / 2 h / 20 °C
5.1: 74 percent / Dess-Martin periodinane / CH2Cl2 / 1.5 h / -40 - 10 °C
6.1: 74 percent / aq. RhCl3 / aq. ethanol / 0.58 h / 115 °C
7.1: 94 percent / P(OMe)3; O2; t-BuOK / tetrahydrofuran; 2-methyl-propan-2-ol / 0.75 h / -40 °C
8.1: 73 percent / VO(acac)2; t-BuOOH / benzene; decane / 10 h / 20 °C
9.1: 72 percent / Et3N / CH2Cl2 / 1 h / -10 - -5 °C
10.1: NaBH4 / methanol / 5 h / 20 °C
11.1: 39 mg / PPTS / CH2Cl2 / 0.5 h / Heating
12.1: 90 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / CH2Cl2 / 18 h / 20 °C
13.1: 96 percent / Et3N / CH2Cl2 / 0.75 h / -78 °C
14.1: 76 percent / Li2CO3 / dimethylformamide / 5 h / 55 °C
15.1: 97 percent / (NH4)6Mo7O24; aq. H2O2 / aq. ethanol / 6 h / 20 °C
16.1: 47 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / benzene / 5 h / Heating
17.1: 76 percent / Na2HPO4; Na(Hg) / methanol / 0.42 h / -20 - -10 °C
18.1: 92 percent / aq. HCl / tetrahydrofuran / 5 h / 20 °C
19.1: 40 percent / SeO2/SiO2 / tetrahydrofuran / 2 h / 80 °C
View Scheme
C28H34O6
827325-46-2

C28H34O6

ingenol
30220-46-3

ingenol

Conditions
ConditionsYield
Multi-step reaction with 11 steps
1: 72 percent / Et3N / CH2Cl2 / 1 h / -10 - -5 °C
2: NaBH4 / methanol / 5 h / 20 °C
3: 39 mg / PPTS / CH2Cl2 / 0.5 h / Heating
4: 90 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / CH2Cl2 / 18 h / 20 °C
5: 96 percent / Et3N / CH2Cl2 / 0.75 h / -78 °C
6: 76 percent / Li2CO3 / dimethylformamide / 5 h / 55 °C
7: 97 percent / (NH4)6Mo7O24; aq. H2O2 / aq. ethanol / 6 h / 20 °C
8: 47 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / benzene / 5 h / Heating
9: 76 percent / Na2HPO4; Na(Hg) / methanol / 0.42 h / -20 - -10 °C
10: 92 percent / aq. HCl / tetrahydrofuran / 5 h / 20 °C
11: 40 percent / SeO2/SiO2 / tetrahydrofuran / 2 h / 80 °C
View Scheme
C31H40O6
827325-48-4

C31H40O6

ingenol
30220-46-3

ingenol

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1: 90 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / CH2Cl2 / 18 h / 20 °C
2: 96 percent / Et3N / CH2Cl2 / 0.75 h / -78 °C
3: 76 percent / Li2CO3 / dimethylformamide / 5 h / 55 °C
4: 97 percent / (NH4)6Mo7O24; aq. H2O2 / aq. ethanol / 6 h / 20 °C
5: 47 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / benzene / 5 h / Heating
6: 76 percent / Na2HPO4; Na(Hg) / methanol / 0.42 h / -20 - -10 °C
7: 92 percent / aq. HCl / tetrahydrofuran / 5 h / 20 °C
8: 40 percent / SeO2/SiO2 / tetrahydrofuran / 2 h / 80 °C
View Scheme
C28H36O6

C28H36O6

ingenol
30220-46-3

ingenol

Conditions
ConditionsYield
Multi-step reaction with 9 steps
1: 39 mg / PPTS / CH2Cl2 / 0.5 h / Heating
2: 90 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / CH2Cl2 / 18 h / 20 °C
3: 96 percent / Et3N / CH2Cl2 / 0.75 h / -78 °C
4: 76 percent / Li2CO3 / dimethylformamide / 5 h / 55 °C
5: 97 percent / (NH4)6Mo7O24; aq. H2O2 / aq. ethanol / 6 h / 20 °C
6: 47 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / benzene / 5 h / Heating
7: 76 percent / Na2HPO4; Na(Hg) / methanol / 0.42 h / -20 - -10 °C
8: 92 percent / aq. HCl / tetrahydrofuran / 5 h / 20 °C
9: 40 percent / SeO2/SiO2 / tetrahydrofuran / 2 h / 80 °C
View Scheme
ingenol
30220-46-3

ingenol

trityl chloride
76-83-5

trityl chloride

ingenol 20-trityl ether
79720-52-8

ingenol 20-trityl ether

Conditions
ConditionsYield
With pyridine Inert atmosphere;96%
In pyridine for 24h;89%
With dmap In pyridine for 16h; Etherification;86%
ingenol
30220-46-3

ingenol

acetic anhydride
108-24-7

acetic anhydride

ingenol 3,5,20-triacetate
30220-45-2

ingenol 3,5,20-triacetate

Conditions
ConditionsYield
In pyridine95%
With pyridine Ambient temperature; Yield given;
ingenol
30220-46-3

ingenol

tert-butyldimethylsilyl chloride
18162-48-6

tert-butyldimethylsilyl chloride

Ingenol-20-(t-butyldimethylsilyl)ether

Ingenol-20-(t-butyldimethylsilyl)ether

Conditions
ConditionsYield
With 2,6-dimethylpyridine In N,N-dimethyl-formamide at 20℃; for 1.5h;95%
In N,N-dimethyl-formamide for 0.75h;75%
[18O]-acetic acid
17217-83-3

[18O]-acetic acid

ingenol
30220-46-3

ingenol

20-[18O2]-acetylingenol

20-[18O2]-acetylingenol

Conditions
ConditionsYield
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 0 - 20℃; for 14h; Mitsunobu Displacement; Inert atmosphere;92%
ingenol
30220-46-3

ingenol

acetic acid
64-19-7

acetic acid

ingenol monoacetate
64280-37-1

ingenol monoacetate

Conditions
ConditionsYield
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 0 - 20℃; Solvent; Temperature; Reagent/catalyst; Mitsunobu Displacement; Inert atmosphere;91%
ingenol
30220-46-3

ingenol

benzoyl chloride
98-88-4

benzoyl chloride

Ingenol-3,5,20-tribenzoat

Ingenol-3,5,20-tribenzoat

Conditions
ConditionsYield
In pyridine90%
ingenol
30220-46-3

ingenol

chlorodiethylisopropylsilane
107149-56-4

chlorodiethylisopropylsilane

A

(1aR,2S,5R,5aS,6S,8aS,9R,10aR)-6-((diethyl(isopropyl)silyl)oxy)-4-(((diethyl(isopropyl)silyl)oxy)methyl)-5,5a-dihydroxy-1,1,7,9-tetramethyl-1a,2,5,5a,6,9,10,10a-octahydro-1H-2,8a-methanocyclopenta[a]cyclopropa[e][10]annulen-11-one

(1aR,2S,5R,5aS,6S,8aS,9R,10aR)-6-((diethyl(isopropyl)silyl)oxy)-4-(((diethyl(isopropyl)silyl)oxy)methyl)-5,5a-dihydroxy-1,1,7,9-tetramethyl-1a,2,5,5a,6,9,10,10a-octahydro-1H-2,8a-methanocyclopenta[a]cyclopropa[e][10]annulen-11-one

B

(1aR,2S,5R,5aR,6S,8aS,9R,10aR)-5-((diethyl(isopropyl)silyl)oxy)-4-(((diethyl(isopropyl)silyl)oxy)methyl)-5a,6-dihydroxy-1,1,7,9-tetramethyl-1a,2,5,5a,6,9,10,10a-octahydro-1H-2,8a-methanocyclopenta[a]cyclopropa[e][10]annulen-11-one

(1aR,2S,5R,5aR,6S,8aS,9R,10aR)-5-((diethyl(isopropyl)silyl)oxy)-4-(((diethyl(isopropyl)silyl)oxy)methyl)-5a,6-dihydroxy-1,1,7,9-tetramethyl-1a,2,5,5a,6,9,10,10a-octahydro-1H-2,8a-methanocyclopenta[a]cyclopropa[e][10]annulen-11-one

Conditions
ConditionsYield
With 1H-imidazole In N,N-dimethyl-formamide at 20℃; for 1.5h;A 87%
B 3.62%
methanol
67-56-1

methanol

ingenol
30220-46-3

ingenol

(1aR,1bS,4R,4aS,5R,6R,7bR,8R,9aR)-3-Hydroxymethyl-6-methoxy-1,1,6,8-tetramethyl-1a,1b,4,5,6,8,9,9a-octahydro-1H-cyclopropa[3,4]benzo[1,2-e]azulene-4,4a,5,7b-tetraol

(1aR,1bS,4R,4aS,5R,6R,7bR,8R,9aR)-3-Hydroxymethyl-6-methoxy-1,1,6,8-tetramethyl-1a,1b,4,5,6,8,9,9a-octahydro-1H-cyclopropa[3,4]benzo[1,2-e]azulene-4,4a,5,7b-tetraol

Conditions
ConditionsYield
With perchloric acid at 20℃; for 16h; Addition; rearrangement;84%
ingenol
30220-46-3

ingenol

acetone
67-64-1

acetone

(6S,6aR,7aR,9R,9aS,12S,12aR,12bR)-12,12a-dihydroxy-2,2,7,7,9,11-hexamethyl-4,6,6a,7,7a,8,9,12,12a,12b-decahydro-6,9a-methanocyclopenta[9,10]cyclopropa[5,6]cyclodeca[1,2-d][1,3]dioxin-13-one
77573-43-4

(6S,6aR,7aR,9R,9aS,12S,12aR,12bR)-12,12a-dihydroxy-2,2,7,7,9,11-hexamethyl-4,6,6a,7,7a,8,9,12,12a,12b-decahydro-6,9a-methanocyclopenta[9,10]cyclopropa[5,6]cyclodeca[1,2-d][1,3]dioxin-13-one

Conditions
ConditionsYield
With toluene-4-sulfonic acid at 20℃; for 1.5h; Product distribution / selectivity;81%
With toluene-4-sulfonic acid for 0.133333h;80%
With methanesulfonic acid In tetrahydrofuran at 45℃;80%
ingenol
30220-46-3

ingenol

acetone
67-64-1

acetone

A

(6S,6aR,7aR,9R,9aS,12S,12aR,12bR)-12,12a-dihydroxy-2,2,7,7,9,11-hexamethyl-4,6,6a,7,7a,8,9,12,12a,12b-decahydro-6,9a-methanocyclopenta[9,10]cyclopropa[5,6]cyclodeca[1,2-d][1,3]dioxin-13-one
77573-43-4

(6S,6aR,7aR,9R,9aS,12S,12aR,12bR)-12,12a-dihydroxy-2,2,7,7,9,11-hexamethyl-4,6,6a,7,7a,8,9,12,12a,12b-decahydro-6,9a-methanocyclopenta[9,10]cyclopropa[5,6]cyclodeca[1,2-d][1,3]dioxin-13-one

B

Ingenol-3,4-acetonid

Ingenol-3,4-acetonid

Conditions
ConditionsYield
With toluene-4-sulfonic acid at 20℃; for 0.5h; Overall yield = 73 %;A 73%
B 4.5%
phthalimide
136918-14-4

phthalimide

ingenol
30220-46-3

ingenol

20-deoxy-20-phthalimidoingenol
256427-45-9

20-deoxy-20-phthalimidoingenol

Conditions
ConditionsYield
With PS-triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 0℃; for 2h; Substitution;67%
ingenol
30220-46-3

ingenol

phenyl isocyanate
103-71-9

phenyl isocyanate

((1aR,2S,5R,5aR,6S,8aS,9R,10aR)-5,5a,6-trihydroxy-1,1,7,9-tetramethyl-11-oxo-1a,2,5,5a,6,9,10,10a-octahydro-1H-2,8a-methanocyclopenta[a]cyclopropa[e][10]annulen-4-yl)methyl phenylcarbamate

((1aR,2S,5R,5aR,6S,8aS,9R,10aR)-5,5a,6-trihydroxy-1,1,7,9-tetramethyl-11-oxo-1a,2,5,5a,6,9,10,10a-octahydro-1H-2,8a-methanocyclopenta[a]cyclopropa[e][10]annulen-4-yl)methyl phenylcarbamate

Conditions
ConditionsYield
With triethylamine In dichloromethane at 20℃; for 2h; Acylation;51%
In dichloromethane; N,N-dimethyl-formamide at 20℃; for 5.33h;45.4%
ingenol
30220-46-3

ingenol

methyl 2-(benzo[d]thiazol-2-ylsulfonyl)acetate
24045-01-0

methyl 2-(benzo[d]thiazol-2-ylsulfonyl)acetate

C30H35NO8S2

C30H35NO8S2

Conditions
ConditionsYield
Stage #1: ingenol; methyl 2-(benzo[d]thiazol-2-ylsulfonyl)acetate With triphenylphosphine In benzene at 0℃; for 0.0833333h;
Stage #2: With di-isopropyl azodicarboxylate In benzene at 0 - 20℃; for 12.5h;
51%
ingenol
30220-46-3

ingenol

di-tert-butylsilyl bis(trifluoromethanesulfonate)
85272-31-7

di-tert-butylsilyl bis(trifluoromethanesulfonate)

ingenol-5,20-(di(tert-butyl)silylene) ether
1356187-16-0

ingenol-5,20-(di(tert-butyl)silylene) ether

Conditions
ConditionsYield
With 2,6-dimethylpyridine In N,N-dimethyl-formamide at 0 - 20℃;50%
(Z)-2-methyl-2-butenoic anhydride
94487-74-8

(Z)-2-methyl-2-butenoic anhydride

ingenol
30220-46-3

ingenol

ingenol 3,20-di-angelate
1356187-34-2

ingenol 3,20-di-angelate

Conditions
ConditionsYield
With caesium carbonate In acetonitrile at 20℃; for 1h;48%
ingenol
30220-46-3

ingenol

tert-butyldimethylsilyl chloride
18162-48-6

tert-butyldimethylsilyl chloride

ingenol-3,20-bis((t-butyldimethyl)silyl)ether

ingenol-3,20-bis((t-butyldimethyl)silyl)ether

Conditions
ConditionsYield
With 1H-imidazole In N,N-dimethyl-formamide for 22h;47%
ingenol
30220-46-3

ingenol

n-butyl isocyanide
111-36-4

n-butyl isocyanide

((1aR,2S,5R,5aR,6S,8aS,9R,10aR)-5,5a,6-trihydroxy-1,1,7,9-tetramethyl-11-oxo-1a,2,5,5a,6,9,10,10a-octahydro-1H-2,8a-methanocyclopenta[a]cyclopropa[e][10]annulen-4-yl)methyl butylcarbamate

((1aR,2S,5R,5aR,6S,8aS,9R,10aR)-5,5a,6-trihydroxy-1,1,7,9-tetramethyl-11-oxo-1a,2,5,5a,6,9,10,10a-octahydro-1H-2,8a-methanocyclopenta[a]cyclopropa[e][10]annulen-4-yl)methyl butylcarbamate

Conditions
ConditionsYield
Stage #1: ingenol; n-butyl isocyanide In dichloromethane; N,N-dimethyl-formamide at 20℃; for 3.66h;
Stage #2: With triethylamine In dichloromethane; N,N-dimethyl-formamide at 20℃; for 18h;
46%
ingenol
30220-46-3

ingenol

benzoic acid
65-85-0

benzoic acid

A

Ingenol-3-benzoate
83036-64-0

Ingenol-3-benzoate

B

Ingenol dibenzoate

Ingenol dibenzoate

Conditions
ConditionsYield
With dmap; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In dichloromethane at -18℃; for 72h; Acylation;A 42%
B 18%
1-chlorocarbonyl-2,3-dihydroindole
117086-91-6

1-chlorocarbonyl-2,3-dihydroindole

ingenol
30220-46-3

ingenol

A

((1aR,2S,5R,5aR,6S,8aS,9R,10aR)-5,5a,6-trihydroxy-1,1,7,9-tetramethyl-11-oxo-1a,2,5,5a,6, 9,10,10a-octahydro-1H-2,8a-methanocyclopenta[a]cyclopropa[e][10]annulen-4-yl)methyl indoline-1-carboxylate

((1aR,2S,5R,5aR,6S,8aS,9R,10aR)-5,5a,6-trihydroxy-1,1,7,9-tetramethyl-11-oxo-1a,2,5,5a,6, 9,10,10a-octahydro-1H-2,8a-methanocyclopenta[a]cyclopropa[e][10]annulen-4-yl)methyl indoline-1-carboxylate

B

(1aR,2S,5R,5aS,6S,8aS,9R,10aR)-5,5a-dihydroxy-4-(((indoline-1-carbonyl)oxy)methyl)-1,1,7,9-tetramethyl-11-oxo-1a,2,5,5a,6,9,10,10a-octahydro-1H-2,8a-methanocyclopenta[a]cyclopropa[e][10]annulen-6-yl indoline-1-carboxylate

(1aR,2S,5R,5aS,6S,8aS,9R,10aR)-5,5a-dihydroxy-4-(((indoline-1-carbonyl)oxy)methyl)-1,1,7,9-tetramethyl-11-oxo-1a,2,5,5a,6,9,10,10a-octahydro-1H-2,8a-methanocyclopenta[a]cyclopropa[e][10]annulen-6-yl indoline-1-carboxylate

Conditions
ConditionsYield
With potassium carbonate In dichloromethane; N,N-dimethyl-formamide at 0 - 20℃;A 42%
B 19%
ingenol
30220-46-3

ingenol

C20H26O5

C20H26O5

Conditions
ConditionsYield
Stage #1: ingenol With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; tetrabutylammomium bromide In dichloromethane at 20℃; for 0.0833333h; pH=8.6; Inert atmosphere;
Stage #2: With N-chloro-succinimide In dichloromethane at 20℃; for 12h; pH=8.6; Reagent/catalyst; Solvent; pH-value; Inert atmosphere;
35%
ingenol
30220-46-3

ingenol

N-(4-chlorophenyl)-N-methylcarbamyl chloride
55239-75-3

N-(4-chlorophenyl)-N-methylcarbamyl chloride

((1aR,2S,5R,5aR,6S,8aS,9R,10aR)-5,5a,6-trihydroxy-1,1,7,9-tetramethyl-11-oxo-1a,2,5,5a,6,9,10,10a-octahydro-1H-2,8a-methanocyclopenta[a]cyclopropa[e][10]annulen-4-yl)methyl (4-chlorophenyl)(methyl)carbamate

((1aR,2S,5R,5aR,6S,8aS,9R,10aR)-5,5a,6-trihydroxy-1,1,7,9-tetramethyl-11-oxo-1a,2,5,5a,6,9,10,10a-octahydro-1H-2,8a-methanocyclopenta[a]cyclopropa[e][10]annulen-4-yl)methyl (4-chlorophenyl)(methyl)carbamate

Conditions
ConditionsYield
Stage #1: ingenol; N-(4-chlorophenyl)-N-methylcarbamyl chloride In N,N-dimethyl-formamide at 0℃; for 0.25h;
Stage #2: With potassium carbonate In N,N-dimethyl-formamide at 0 - 20℃; for 48h;
19.98%
ingenol
30220-46-3

ingenol

2-chloro-5-(trifluoromethyl)pyrimidine
69034-12-4

2-chloro-5-(trifluoromethyl)pyrimidine

(1aR,2S,5R,5aR,6S,8aS,9R,10aR)-5,5a,6-trihydroxy-1,1,7,9-tetramethyl-4-(((5-(trifluoromethyl)pyrimidin-2-yl)oxy)methyl)-1a,2,5,5a,6,9,10,10a-octahydro-1H-2,8a-methanocyclopenta[a]cyclopropa[e][10]annulen-11-one

(1aR,2S,5R,5aR,6S,8aS,9R,10aR)-5,5a,6-trihydroxy-1,1,7,9-tetramethyl-4-(((5-(trifluoromethyl)pyrimidin-2-yl)oxy)methyl)-1a,2,5,5a,6,9,10,10a-octahydro-1H-2,8a-methanocyclopenta[a]cyclopropa[e][10]annulen-11-one

Conditions
ConditionsYield
With triethylamine In N,N-dimethyl-formamide at 20℃; for 39.5h;5%
ingenol
30220-46-3

ingenol

benzyl isothiocyanate
3173-56-6

benzyl isothiocyanate

((1aR,2S,5R,5aR,6S,8aS,9R,10aR)-5,5a,6-trihydroxy-1,1,7,9-tetramethyl-11-oxo-1a,2,5,5a,6,9,10,10a-octahydro-1H-2,8a-methanocyclopenta[a]cyclopropa[e][10]annulen-4-yl)methyl benzylcarbamate

((1aR,2S,5R,5aR,6S,8aS,9R,10aR)-5,5a,6-trihydroxy-1,1,7,9-tetramethyl-11-oxo-1a,2,5,5a,6,9,10,10a-octahydro-1H-2,8a-methanocyclopenta[a]cyclopropa[e][10]annulen-4-yl)methyl benzylcarbamate

Conditions
ConditionsYield
With triethylamine In N,N-dimethyl-formamide at 20℃;4.7%

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