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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. DayangChem can provide different quantities

Brassinolide Manufacturer/High quality/Best price/In stock

Cas:72962-43-7

Min.Order:1 Kilogram

FOB Price: $3.0

Type:Lab/Research institutions

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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 Brassinolide supplier in China

Cas:72962-43-7

Min.Order:0 Metric Ton

Negotiable

Type:Manufacturers

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Hefei TNJ chemical industry co.,ltd

Novel PGR for seed soaking or stem and leaves spraying. 1. Prompt growth 2. Improve quality 3. Increase quantity 4. Bright colors of leaves and flowers, thicken the foliar 5. Enhance weight and sugar content in fruit. 6. Advance time fo

brassinolide

Cas:72962-43-7

Min.Order:1 Kilogram

Negotiable

Type:Trading Company

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Ality Chemical Corporation

The above product is Ality Chemical's strong item with best price, good quality and fast supply. Ality Chemical has been focusing on the research and production of this field for over 14 years. At the same time, we are always committed to providi

Factory Supply Brassinolide

Cas:72962-43-7

Min.Order:1

Negotiable

Type:Other

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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

brassinolide powder from GMP manufacture with reasonable price

Cas:72962-43-7

Min.Order:1 Gram

FOB Price: $0.1

Type:Manufacturers

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COLORCOM LTD.

Colorcom is a global leader in industrial chemical manufacturing and is continuously innovating and transforming to exceed client expectations and industry standards. Colorcom prides itself on superior customer and technical focus, while focusing on

Brassinolide

Cas:72962-43-7

Min.Order:1 Metric Ton

Negotiable

Type:Manufacturers

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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

24-(S)-Epibrassinolide

Cas:72962-43-7

Min.Order:5 Kiloliter

FOB Price: $1.2 / 5.0

Type:Manufacturers

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Hubei DiBo chemical co., LTD

Name: epibrassinolide CAS no. : 72962-43-7 Molecular formula: C28H48O6 Molecular weight:480.6771 Product Quality 12 years of chemical raw materials Mature operation of the industry System stability Data storage Security without vulnerabil

epibrassinolide /CAS :72962-43-7/raw material/high-quality

Cas:72962-43-7

Min.Order:25 Kilogram

FOB Price: $1.0 / 2.0

Type:Other

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

Brassinolide

Cas:72962-43-7

Min.Order:1 Gram

FOB Price: $1000.0 / 1300.0

Type:Trading Company

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Henan Tianfu Chemical Co., Ltd.

best service,quality & low price 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,Mer

Brassinolide /72962-43-7

Cas:72962-43-7

Min.Order:1 Kilogram

Negotiable

Type:Lab/Research institutions

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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

Factory direct supply CAS 72962-43-7 with best quality

Cas:72962-43-7

Min.Order:1 Kilogram

FOB Price: $139.0 / 210.0

Type:Trading Company

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Henan Sinotech Import&Export Corporation

Product name Plant Growth Regulator Brassinolide(BR) 90% TC, 0.1%SP General info Function: Plant Growth Regulator

Brassinolide

Cas:72962-43-7

Min.Order:5 Metric Ton

FOB Price: $1.0 / 2.0

Type:Other

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

Xi'an Faithful Biotech Co., Ltd.

We are the manufacturers and suppliers of API in China, and warehouse in Germany and USA of California, which can quickly and safely deliver to your address 1.High quality and competitive price. 2.Free sample for your evaluation. 3.Promptly delivery

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 present

Brassinolide

Cas:72962-43-7

Min.Order:10 Gram

FOB Price: $100.0 / 120.0

Type:Trading Company

inquiry

Qingdao Beluga Import and Export Co., LTD

Brassinolide CAS:72962-43-7 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 intermediate

Brassinolide CAS:72962-43-7

Cas:72962-43-7

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

Hebei Mojin Biotechnology Co.,Ltd

Hebei Mojin Biotechnology Co., Ltd,Our business covers more than 30 countries, most of the big customers come from Europe, America and other countries in the world, we can guarantee the quality and price. In recent decades, with the efforts of all em

Brassinolide CAS 72962-43-7

Cas:72962-43-7

Min.Order:1 Gram

FOB Price: $95.0 / 100.0

Type:Trading Company

inquiry

Changchun Artel lmport and Export trade company

Product Detail Minimum Order Qty. 10 Gram

Leader Biochemical Group

PRODUCT DETAILS

China Largest Manufacturer factory sales Brassinolide CAS 72962-43-7

Cas:72962-43-7

Min.Order:500 Kilogram

FOB Price: $1.0 / 2.0

Type:Lab/Research institutions

inquiry

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

Rely Chemicals Ltd.

1.quick response;2.competitive price with good quality product;3.flexible payment;4.fast delivery;5.superior after sell service. Appearance:White powder Package:as customerized Application:Promote the growth of plant to increase yield,etc . 2. K

brassinolide 90%TC 0.1%SP

Cas:72962-43-7

Min.Order:1 Kilogram

Negotiable

Type:Trading Company

inquiry

SHANGHAI T&W PHARMACEUTICAL CO., LTD.

A substitute for perfluorooctanoic acid, mainly used as a surfactant, dispersant, additive, etc Appearance:White solid or Colorless liquid Purity:99.3 % We will ship the goods in a timely manner as required We can provide relevant documents acc

Brassinolide

Cas:72962-43-7

Min.Order:4 Kilogram

Negotiable

Type:Lab/Research institutions

inquiry

Shanghai Massive Chemical Technology Co., Ltd.

Massive Chemical is certified with ISO9001 and ISO14001 manufacturer for this product. We will offer all documents as requirement for the materials which includes, Certificate of Analysis, Material Safety Data Sheet, and Method of Analysis and

Brassinolide/High quality/Best price

Cas:72962-43-7

Min.Order:1 Gram

FOB Price: $1.0

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 Brassinolide

Cas:72962-43-7

Min.Order:10 Gram

FOB Price: $100.0

Type:Lab/Research institutions

inquiry

Hangzhou Lingrui Chemical Co.,Ltd.

High purity Brassinolide 72962-43-7 in stock immediately delivery good supplierAppearance:Powder Storage:Dry and ventilated Package:according to customers' requirements Application:APIs Transportation:By air(EMS or EUB or FedEx or TNT ect...) or by s

Siwei Development Group Ltd.

Product name: Epibrassinolide CAS No.:72962-43-7 Molecule Formula:C28H48O6 Molecule Weight:480.67 Purity: 98.0% Package: 25kg/drum Description:White powder Manufacture Standards:Enterprise Standard TESTING ITEMS S

Best Quality Epibrassinolide

Cas:72962-43-7

Min.Order:1 Kilogram

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,

Brassinolide

Cas:72962-43-7

Min.Order:1 Milligram

Negotiable

Type:Trading Company

inquiry

Hangzhou Fandachem Co.,Ltd

Hangzhou Fandachem Co.,Ltd, a China-based chemical company, specialize in exporting Brassinolide (BR)90%TC, 0.01%SP, 0.1%SP, CAS NO: 72962-43-7 Please contact us by email freely. We are leading exporter in China. If you really ne

Brassinolide (BR)90%TC, 0.01%SP, 0.1%SP, CAS NO: 72962-43-7

Cas:72962-43-7

Min.Order:1 Kilogram

Negotiable

Type:Other

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

Synthetic route

2α,3α-22R,23R-tetraacetoxy-B-homo-7-oxa-24S-methyl-5α-cholestan-6-one
76987-58-1

2α,3α-22R,23R-tetraacetoxy-B-homo-7-oxa-24S-methyl-5α-cholestan-6-one

(3α,5α,6α,8β,9α,12β,13β,16α,17β)-10-[(2'α,3'β,4'β,5'β)-3,4-dihydroxy-5,6-dimethyl-2-heptanyl]-5,6-dihydroxy-7a,9a-dimethylhexadecahydro-3H-benzo[c]indeno[5,4-e]oxepin-3-one
72962-43-7

(3α,5α,6α,8β,9α,12β,13β,16α,17β)-10-[(2'α,3'β,4'β,5'β)-3,4-dihydroxy-5,6-dimethyl-2-heptanyl]-5,6-dihydroxy-7a,9a-dimethylhexadecahydro-3H-benzo[c]indeno[5,4-e]oxepin-3-one

Conditions
ConditionsYield
With potassium hydroxide In methanol for 1h; Heating;94%
With sodium hydroxide In methanol; water for 3h; Heating;57%
With hydrogenchloride; methanol; potassium hydroxide 1.) reflux, 1 h, 2.) room temperature, 1 h; Yield given. Multistep reaction;
Multi-step reaction with 2 steps
1: NaOH
2: HCl
View Scheme
(2R,3S,5S,8S,9S,10R,13S,14S,17R)-17-{(S)-1-[(4R,5R)-5-((S)-1,2-Dimethyl-propyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-ethyl}-2,3-dihydroxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-6-one
83066-72-2

(2R,3S,5S,8S,9S,10R,13S,14S,17R)-17-{(S)-1-[(4R,5R)-5-((S)-1,2-Dimethyl-propyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-ethyl}-2,3-dihydroxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-6-one

A

(3α,5α,6α,8β,9α,12β,13β,16α,17β)-10-[(2'α,3'β,4'β,5'β)-3,4-dihydroxy-5,6-dimethyl-2-heptanyl]-5,6-dihydroxy-7a,9a-dimethylhexadecahydro-3H-benzo[c]indeno[5,4-e]oxepin-3-one
72962-43-7

(3α,5α,6α,8β,9α,12β,13β,16α,17β)-10-[(2'α,3'β,4'β,5'β)-3,4-dihydroxy-5,6-dimethyl-2-heptanyl]-5,6-dihydroxy-7a,9a-dimethylhexadecahydro-3H-benzo[c]indeno[5,4-e]oxepin-3-one

B

(22R,23R,24S)-2α,3α,22,23-tetrahydroxy-6-oxa-7a-homo-5α-campestan-7-one
146205-07-4

(22R,23R,24S)-2α,3α,22,23-tetrahydroxy-6-oxa-7a-homo-5α-campestan-7-one

Conditions
ConditionsYield
With trifluoroacetyl peroxide In dichloromethane at 22℃; for 1h;A 74%
B n/a
(2R,3S,5α,22R,23R,24S)-6,6-Ethylenedioxy-2,3-isopropylidenedioxyergostane-22,23-diol
91708-76-8

(2R,3S,5α,22R,23R,24S)-6,6-Ethylenedioxy-2,3-isopropylidenedioxyergostane-22,23-diol

(3α,5α,6α,8β,9α,12β,13β,16α,17β)-10-[(2'α,3'β,4'β,5'β)-3,4-dihydroxy-5,6-dimethyl-2-heptanyl]-5,6-dihydroxy-7a,9a-dimethylhexadecahydro-3H-benzo[c]indeno[5,4-e]oxepin-3-one
72962-43-7

(3α,5α,6α,8β,9α,12β,13β,16α,17β)-10-[(2'α,3'β,4'β,5'β)-3,4-dihydroxy-5,6-dimethyl-2-heptanyl]-5,6-dihydroxy-7a,9a-dimethylhexadecahydro-3H-benzo[c]indeno[5,4-e]oxepin-3-one

Conditions
ConditionsYield
With trifluoroacetyl peroxide; trifluoroacetic acid In chloroform for 3h; Ambient temperature;53%
Multi-step reaction with 3 steps
1: 7.62 g / 80percent AcOH / H2O / 1 h / 50 - 60 °C
2: pyridine, N,N-dimethylaminopyridine
View Scheme
3-dehydroteasterone
124853-28-7

3-dehydroteasterone

(3α,5α,6α,8β,9α,12β,13β,16α,17β)-10-[(2'α,3'β,4'β,5'β)-3,4-dihydroxy-5,6-dimethyl-2-heptanyl]-5,6-dihydroxy-7a,9a-dimethylhexadecahydro-3H-benzo[c]indeno[5,4-e]oxepin-3-one
72962-43-7

(3α,5α,6α,8β,9α,12β,13β,16α,17β)-10-[(2'α,3'β,4'β,5'β)-3,4-dihydroxy-5,6-dimethyl-2-heptanyl]-5,6-dihydroxy-7a,9a-dimethylhexadecahydro-3H-benzo[c]indeno[5,4-e]oxepin-3-one

Conditions
ConditionsYield
With amalgamated zinc; osmium(VIII) oxide; chloro-trimethyl-silane; trifluoroacetyl peroxide; 4-methylmorpholine N-oxide 1.) THF, rt., 12 h; 2.) THF, aq. t-BuOH; 3.) CH2Cl2; Yield given. Multistep reaction;
castasterone
80736-41-0

castasterone

(3α,5α,6α,8β,9α,12β,13β,16α,17β)-10-[(2'α,3'β,4'β,5'β)-3,4-dihydroxy-5,6-dimethyl-2-heptanyl]-5,6-dihydroxy-7a,9a-dimethylhexadecahydro-3H-benzo[c]indeno[5,4-e]oxepin-3-one
72962-43-7

(3α,5α,6α,8β,9α,12β,13β,16α,17β)-10-[(2'α,3'β,4'β,5'β)-3,4-dihydroxy-5,6-dimethyl-2-heptanyl]-5,6-dihydroxy-7a,9a-dimethylhexadecahydro-3H-benzo[c]indeno[5,4-e]oxepin-3-one

Conditions
ConditionsYield
Yield given. Multistep reaction;
Multi-step reaction with 2 steps
1: pyridine, N,N-dimethylaminopyridine
View Scheme
2,3,22,23-tetra-O-acetylcastasterone
77027-48-6

2,3,22,23-tetra-O-acetylcastasterone

(3α,5α,6α,8β,9α,12β,13β,16α,17β)-10-[(2'α,3'β,4'β,5'β)-3,4-dihydroxy-5,6-dimethyl-2-heptanyl]-5,6-dihydroxy-7a,9a-dimethylhexadecahydro-3H-benzo[c]indeno[5,4-e]oxepin-3-one
72962-43-7

(3α,5α,6α,8β,9α,12β,13β,16α,17β)-10-[(2'α,3'β,4'β,5'β)-3,4-dihydroxy-5,6-dimethyl-2-heptanyl]-5,6-dihydroxy-7a,9a-dimethylhexadecahydro-3H-benzo[c]indeno[5,4-e]oxepin-3-one

Conditions
ConditionsYield
Yield given. Multistep reaction;
Acetic acid (1R,2R,3S)-2-acetoxy-1-[(S)-1-((1R,3aS,3bS,6aS,8S,9R,10aR,10bS,12aS)-8,9-dihydroxy-10a,12a-dimethyl-6-oxo-hexadecahydro-5-oxa-benzo[3,4]cyclohepta[1,2-e]inden-1-yl)-ethyl]-3,4-dimethyl-pentyl ester
106315-18-8

Acetic acid (1R,2R,3S)-2-acetoxy-1-[(S)-1-((1R,3aS,3bS,6aS,8S,9R,10aR,10bS,12aS)-8,9-dihydroxy-10a,12a-dimethyl-6-oxo-hexadecahydro-5-oxa-benzo[3,4]cyclohepta[1,2-e]inden-1-yl)-ethyl]-3,4-dimethyl-pentyl ester

(3α,5α,6α,8β,9α,12β,13β,16α,17β)-10-[(2'α,3'β,4'β,5'β)-3,4-dihydroxy-5,6-dimethyl-2-heptanyl]-5,6-dihydroxy-7a,9a-dimethylhexadecahydro-3H-benzo[c]indeno[5,4-e]oxepin-3-one
72962-43-7

(3α,5α,6α,8β,9α,12β,13β,16α,17β)-10-[(2'α,3'β,4'β,5'β)-3,4-dihydroxy-5,6-dimethyl-2-heptanyl]-5,6-dihydroxy-7a,9a-dimethylhexadecahydro-3H-benzo[c]indeno[5,4-e]oxepin-3-one

Conditions
ConditionsYield
With sodium hydroxide In methanol for 3h; Heating;1.79 g
(1S,2R,4R,5S)-2-[(1R,3aS,4S,5S,7aS)-1-((1S,2R,3R,4S)-2,3-Dihydroxy-1,4,5-trimethyl-hexyl)-4-hydroxymethyl-7a-methyl-octahydro-inden-5-yl]-4,5-dihydroxy-2-methyl-cyclohexanecarboxylic acid

(1S,2R,4R,5S)-2-[(1R,3aS,4S,5S,7aS)-1-((1S,2R,3R,4S)-2,3-Dihydroxy-1,4,5-trimethyl-hexyl)-4-hydroxymethyl-7a-methyl-octahydro-inden-5-yl]-4,5-dihydroxy-2-methyl-cyclohexanecarboxylic acid

(3α,5α,6α,8β,9α,12β,13β,16α,17β)-10-[(2'α,3'β,4'β,5'β)-3,4-dihydroxy-5,6-dimethyl-2-heptanyl]-5,6-dihydroxy-7a,9a-dimethylhexadecahydro-3H-benzo[c]indeno[5,4-e]oxepin-3-one
72962-43-7

(3α,5α,6α,8β,9α,12β,13β,16α,17β)-10-[(2'α,3'β,4'β,5'β)-3,4-dihydroxy-5,6-dimethyl-2-heptanyl]-5,6-dihydroxy-7a,9a-dimethylhexadecahydro-3H-benzo[c]indeno[5,4-e]oxepin-3-one

Conditions
ConditionsYield
With hydrogenchloride
(1R,3aS,3bS,5aS,6aS,9aR,10aR,10bS,12aS)-1-{(S)-1-[(4R,5R)-5-((S)-1,2-Dimethyl-propyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-ethyl}-8,8,10a,12a-tetramethyl-hexadecahydro-7,9-dioxa-dicyclopenta[a,h]phenanthren-5-one
111118-49-1

(1R,3aS,3bS,5aS,6aS,9aR,10aR,10bS,12aS)-1-{(S)-1-[(4R,5R)-5-((S)-1,2-Dimethyl-propyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-ethyl}-8,8,10a,12a-tetramethyl-hexadecahydro-7,9-dioxa-dicyclopenta[a,h]phenanthren-5-one

A

(3α,5α,6α,8β,9α,12β,13β,16α,17β)-10-[(2'α,3'β,4'β,5'β)-3,4-dihydroxy-5,6-dimethyl-2-heptanyl]-5,6-dihydroxy-7a,9a-dimethylhexadecahydro-3H-benzo[c]indeno[5,4-e]oxepin-3-one
72962-43-7

(3α,5α,6α,8β,9α,12β,13β,16α,17β)-10-[(2'α,3'β,4'β,5'β)-3,4-dihydroxy-5,6-dimethyl-2-heptanyl]-5,6-dihydroxy-7a,9a-dimethylhexadecahydro-3H-benzo[c]indeno[5,4-e]oxepin-3-one

B

(22R,23R,24S)-2α,3α,22,23-tetrahydroxy-6-oxa-7a-homo-5α-campestan-7-one
146205-07-4

(22R,23R,24S)-2α,3α,22,23-tetrahydroxy-6-oxa-7a-homo-5α-campestan-7-one

Conditions
ConditionsYield
Yield given. Multistep reaction. Yields of byproduct given;
(20S)-6,6-ethylenedioxy-2α,3α-isopropylidenedioxy-5α-pregnane-20-carbaldehyde
81481-15-4

(20S)-6,6-ethylenedioxy-2α,3α-isopropylidenedioxy-5α-pregnane-20-carbaldehyde

(3α,5α,6α,8β,9α,12β,13β,16α,17β)-10-[(2'α,3'β,4'β,5'β)-3,4-dihydroxy-5,6-dimethyl-2-heptanyl]-5,6-dihydroxy-7a,9a-dimethylhexadecahydro-3H-benzo[c]indeno[5,4-e]oxepin-3-one
72962-43-7

(3α,5α,6α,8β,9α,12β,13β,16α,17β)-10-[(2'α,3'β,4'β,5'β)-3,4-dihydroxy-5,6-dimethyl-2-heptanyl]-5,6-dihydroxy-7a,9a-dimethylhexadecahydro-3H-benzo[c]indeno[5,4-e]oxepin-3-one

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 1.) n-BuLi, 2.) 30percent H2O2 / 1.) THF, -78 deg C, 3 h, 2.) acetic acid, room temperature, 15 h
2: 85 percent / Ti(O-iPr)4, (+)-L-diethyl tartrate, cumene hydroperoxide, 4 Angstroem MS / CH2Cl2 / 144 h / -25 °C
3: 82 percent / CuCN / diethyl ether / 1.) -78 deg C, 2 h, 2.) 0 deg C, 3 h
4: 53 percent / CF3CO3H, CF3CO2H / CHCl3 / 3 h / Ambient temperature
View Scheme
Multi-step reaction with 8 steps
1: n-BuLi / tetrahydrofuran; hexane / -50 to -60 deg C; -40 deg C, 1 h; -68 to - 65 deg C, 1 h; 0 deg C
2: 74.6 percent / 1.) triphenylphosphine, benzoic acid, diethyl azodicarboxylate; 2.) K2CO3 / 1.) THF, 5-10 deg C, 30 min; 2.) THF/methanol, reflux, 3 h
3: 44.3 g / H2, 1M NaBH4, ethylenediamine, nickel acetate / aq. ethanol / 5 h
4: 93 percent / m-chloroperbenzoic acid, Na2HPO4 / CH2Cl2 / 20 h / 5 °C
5: n-BuLi / hexane; cyclohexane / -70 deg C, 1 h; 10 deg C, 4 h
6: 7.62 g / 80percent AcOH / H2O / 1 h / 50 - 60 °C
7: pyridine, N,N-dimethylaminopyridine
View Scheme
Multi-step reaction with 7 steps
1: 26.93 g / n-BuLi / tetrahydrofuran; hexane / -50 to -60 deg C; -40 deg C, 1 h; -68 to - 65 deg C, 1 h; 0 deg C
2: 44.3 g / H2, 1M NaBH4, ethylenediamine, nickel acetate / aq. ethanol / 5 h
3: 93 percent / m-chloroperbenzoic acid, Na2HPO4 / CH2Cl2 / 20 h / 5 °C
4: n-BuLi / hexane; cyclohexane / -70 deg C, 1 h; 10 deg C, 4 h
5: 7.62 g / 80percent AcOH / H2O / 1 h / 50 - 60 °C
6: pyridine, N,N-dimethylaminopyridine
View Scheme
(2α,3α,5α,22S,23E)-6,6-ethylenedioxy-2,3-isopropylidenedioxy-26,27-dinorcholest-23-en-22-ol
148705-11-7

(2α,3α,5α,22S,23E)-6,6-ethylenedioxy-2,3-isopropylidenedioxy-26,27-dinorcholest-23-en-22-ol

(3α,5α,6α,8β,9α,12β,13β,16α,17β)-10-[(2'α,3'β,4'β,5'β)-3,4-dihydroxy-5,6-dimethyl-2-heptanyl]-5,6-dihydroxy-7a,9a-dimethylhexadecahydro-3H-benzo[c]indeno[5,4-e]oxepin-3-one
72962-43-7

(3α,5α,6α,8β,9α,12β,13β,16α,17β)-10-[(2'α,3'β,4'β,5'β)-3,4-dihydroxy-5,6-dimethyl-2-heptanyl]-5,6-dihydroxy-7a,9a-dimethylhexadecahydro-3H-benzo[c]indeno[5,4-e]oxepin-3-one

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 85 percent / Ti(O-iPr)4, (+)-L-diethyl tartrate, cumene hydroperoxide, 4 Angstroem MS / CH2Cl2 / 144 h / -25 °C
2: 82 percent / CuCN / diethyl ether / 1.) -78 deg C, 2 h, 2.) 0 deg C, 3 h
3: 53 percent / CF3CO3H, CF3CO2H / CHCl3 / 3 h / Ambient temperature
View Scheme
(2R,3S,5α,22R)-23,24-epoxy-6,6-(ethylenedioxy)-2,3-(isopropylidenedioxy)-26,27-dinorcholestan-22-ol
223117-11-1

(2R,3S,5α,22R)-23,24-epoxy-6,6-(ethylenedioxy)-2,3-(isopropylidenedioxy)-26,27-dinorcholestan-22-ol

(3α,5α,6α,8β,9α,12β,13β,16α,17β)-10-[(2'α,3'β,4'β,5'β)-3,4-dihydroxy-5,6-dimethyl-2-heptanyl]-5,6-dihydroxy-7a,9a-dimethylhexadecahydro-3H-benzo[c]indeno[5,4-e]oxepin-3-one
72962-43-7

(3α,5α,6α,8β,9α,12β,13β,16α,17β)-10-[(2'α,3'β,4'β,5'β)-3,4-dihydroxy-5,6-dimethyl-2-heptanyl]-5,6-dihydroxy-7a,9a-dimethylhexadecahydro-3H-benzo[c]indeno[5,4-e]oxepin-3-one

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 82 percent / CuCN / diethyl ether / 1.) -78 deg C, 2 h, 2.) 0 deg C, 3 h
2: 53 percent / CF3CO3H, CF3CO2H / CHCl3 / 3 h / Ambient temperature
View Scheme
3-methyl-butan-2-one
563-80-4

3-methyl-butan-2-one

ethyl halide

ethyl halide

(3α,5α,6α,8β,9α,12β,13β,16α,17β)-10-[(2'α,3'β,4'β,5'β)-3,4-dihydroxy-5,6-dimethyl-2-heptanyl]-5,6-dihydroxy-7a,9a-dimethylhexadecahydro-3H-benzo[c]indeno[5,4-e]oxepin-3-one
72962-43-7

(3α,5α,6α,8β,9α,12β,13β,16α,17β)-10-[(2'α,3'β,4'β,5'β)-3,4-dihydroxy-5,6-dimethyl-2-heptanyl]-5,6-dihydroxy-7a,9a-dimethylhexadecahydro-3H-benzo[c]indeno[5,4-e]oxepin-3-one

Conditions
ConditionsYield
Multi-step reaction with 10 steps
1: Br2 / methanol
2: acetone / 18 h / Heating
3: NaH / tetrahydrofuran / 0.5 h / 25 °C
4: 80 percent / LDA / tetrahydrofuran / 1.) -40 to -50 deg C, 30 min, 2.) -75 deg C, 14 h
5: 83 percent / H2, pyridine / 10percent Pd/C / ethanol; tetrahydrofuran / 14 h / 2585.7 Torr / Ambient temperature
6: 99 percent / LAH / tetrahydrofuran / 1.) r.t. 2 h, 2.) reflux, overnight
7: 96 percent / CSA / 24 h / Ambient temperature
8: 91 percent / CrO3, pyridine / CH2Cl2 / 48 h / Ambient temperature
9: 72 percent / <(C6H5)3P>3RhCl / benzene / 5 h / Heating
View Scheme
Multi-step reaction with 10 steps
1: Br2 / methanol
2: acetone / 18 h / Heating
3: 1.) NaH, triethylphosphonoacetate, 2.) aq. KOH / 1.) THF, 25 deg C, 30 min, 2.) 25 deg C, 24 h
4: 80 percent / LDA / tetrahydrofuran / 1.) -40 to -50 deg C, 30 min, 2.) -75 deg C, 14 h
5: 83 percent / H2, pyridine / 10percent Pd/C / ethanol; tetrahydrofuran / 14 h / 2585.7 Torr / Ambient temperature
6: 99 percent / LAH / tetrahydrofuran / 1.) r.t. 2 h, 2.) reflux, overnight
7: 96 percent / CSA / 24 h / Ambient temperature
8: 91 percent / CrO3, pyridine / CH2Cl2 / 48 h / Ambient temperature
9: 72 percent / <(C6H5)3P>3RhCl / benzene / 5 h / Heating
View Scheme
4-(1-methylethyl)furan-2(5H)-one
10547-89-4

4-(1-methylethyl)furan-2(5H)-one

(3α,5α,6α,8β,9α,12β,13β,16α,17β)-10-[(2'α,3'β,4'β,5'β)-3,4-dihydroxy-5,6-dimethyl-2-heptanyl]-5,6-dihydroxy-7a,9a-dimethylhexadecahydro-3H-benzo[c]indeno[5,4-e]oxepin-3-one
72962-43-7

(3α,5α,6α,8β,9α,12β,13β,16α,17β)-10-[(2'α,3'β,4'β,5'β)-3,4-dihydroxy-5,6-dimethyl-2-heptanyl]-5,6-dihydroxy-7a,9a-dimethylhexadecahydro-3H-benzo[c]indeno[5,4-e]oxepin-3-one

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1: 80 percent / LDA / tetrahydrofuran / 1.) -40 to -50 deg C, 30 min, 2.) -75 deg C, 14 h
2: 83 percent / H2, pyridine / 10percent Pd/C / ethanol; tetrahydrofuran / 14 h / 2585.7 Torr / Ambient temperature
3: 99 percent / LAH / tetrahydrofuran / 1.) r.t. 2 h, 2.) reflux, overnight
4: 96 percent / CSA / 24 h / Ambient temperature
5: 91 percent / CrO3, pyridine / CH2Cl2 / 48 h / Ambient temperature
6: 72 percent / <(C6H5)3P>3RhCl / benzene / 5 h / Heating
View Scheme
1-(acetyloxy)-3-methyl-2-butanone
36960-07-3

1-(acetyloxy)-3-methyl-2-butanone

(3α,5α,6α,8β,9α,12β,13β,16α,17β)-10-[(2'α,3'β,4'β,5'β)-3,4-dihydroxy-5,6-dimethyl-2-heptanyl]-5,6-dihydroxy-7a,9a-dimethylhexadecahydro-3H-benzo[c]indeno[5,4-e]oxepin-3-one
72962-43-7

(3α,5α,6α,8β,9α,12β,13β,16α,17β)-10-[(2'α,3'β,4'β,5'β)-3,4-dihydroxy-5,6-dimethyl-2-heptanyl]-5,6-dihydroxy-7a,9a-dimethylhexadecahydro-3H-benzo[c]indeno[5,4-e]oxepin-3-one

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1: NaH / tetrahydrofuran / 0.5 h / 25 °C
2: 80 percent / LDA / tetrahydrofuran / 1.) -40 to -50 deg C, 30 min, 2.) -75 deg C, 14 h
3: 83 percent / H2, pyridine / 10percent Pd/C / ethanol; tetrahydrofuran / 14 h / 2585.7 Torr / Ambient temperature
4: 99 percent / LAH / tetrahydrofuran / 1.) r.t. 2 h, 2.) reflux, overnight
5: 96 percent / CSA / 24 h / Ambient temperature
6: 91 percent / CrO3, pyridine / CH2Cl2 / 48 h / Ambient temperature
7: 72 percent / <(C6H5)3P>3RhCl / benzene / 5 h / Heating
View Scheme
Multi-step reaction with 8 steps
1: 1.) NaH, triethylphosphonoacetate, 2.) aq. KOH / 1.) THF, 25 deg C, 30 min, 2.) 25 deg C, 24 h
2: 80 percent / LDA / tetrahydrofuran / 1.) -40 to -50 deg C, 30 min, 2.) -75 deg C, 14 h
3: 83 percent / H2, pyridine / 10percent Pd/C / ethanol; tetrahydrofuran / 14 h / 2585.7 Torr / Ambient temperature
4: 99 percent / LAH / tetrahydrofuran / 1.) r.t. 2 h, 2.) reflux, overnight
5: 96 percent / CSA / 24 h / Ambient temperature
6: 91 percent / CrO3, pyridine / CH2Cl2 / 48 h / Ambient temperature
7: 72 percent / <(C6H5)3P>3RhCl / benzene / 5 h / Heating
View Scheme
(22E)-stigmasta-2,22-dien-6-one
74174-45-1

(22E)-stigmasta-2,22-dien-6-one

(3α,5α,6α,8β,9α,12β,13β,16α,17β)-10-[(2'α,3'β,4'β,5'β)-3,4-dihydroxy-5,6-dimethyl-2-heptanyl]-5,6-dihydroxy-7a,9a-dimethylhexadecahydro-3H-benzo[c]indeno[5,4-e]oxepin-3-one
72962-43-7

(3α,5α,6α,8β,9α,12β,13β,16α,17β)-10-[(2'α,3'β,4'β,5'β)-3,4-dihydroxy-5,6-dimethyl-2-heptanyl]-5,6-dihydroxy-7a,9a-dimethylhexadecahydro-3H-benzo[c]indeno[5,4-e]oxepin-3-one

Conditions
ConditionsYield
Multi-step reaction with 11 steps
1: 72 percent / OsO4, NMO, H2O / acetone; 2-methyl-propan-2-ol / 12 h / Ambient temperature
2: 98 percent / CSA / acetonitrile; CH2Cl2 / 1 h / Ambient temperature
3: OsO4, NMO, aq. NaHCO3, MeSO2NH2 / tetrahydrofuran; 2-methyl-propan-2-ol / 144 h / 40 °C
4: 82 percent / pyridine, NaHCO3, H5IO6 / tetrahydrofuran / 24 h / Ambient temperature
5: 80 percent / LDA / tetrahydrofuran / 1.) -40 to -50 deg C, 30 min, 2.) -75 deg C, 14 h
6: 83 percent / H2, pyridine / 10percent Pd/C / ethanol; tetrahydrofuran / 14 h / 2585.7 Torr / Ambient temperature
7: 99 percent / LAH / tetrahydrofuran / 1.) r.t. 2 h, 2.) reflux, overnight
8: 96 percent / CSA / 24 h / Ambient temperature
9: 91 percent / CrO3, pyridine / CH2Cl2 / 48 h / Ambient temperature
10: 72 percent / <(C6H5)3P>3RhCl / benzene / 5 h / Heating
View Scheme
(22E,24S)-3β,5-cyclo-24-ethylcholest-22-en-6-one
74174-49-5

(22E,24S)-3β,5-cyclo-24-ethylcholest-22-en-6-one

(3α,5α,6α,8β,9α,12β,13β,16α,17β)-10-[(2'α,3'β,4'β,5'β)-3,4-dihydroxy-5,6-dimethyl-2-heptanyl]-5,6-dihydroxy-7a,9a-dimethylhexadecahydro-3H-benzo[c]indeno[5,4-e]oxepin-3-one
72962-43-7

(3α,5α,6α,8β,9α,12β,13β,16α,17β)-10-[(2'α,3'β,4'β,5'β)-3,4-dihydroxy-5,6-dimethyl-2-heptanyl]-5,6-dihydroxy-7a,9a-dimethylhexadecahydro-3H-benzo[c]indeno[5,4-e]oxepin-3-one

Conditions
ConditionsYield
Multi-step reaction with 12 steps
1: 80 percent / pyridine hydrochloride, LiBr / N,N-dimethyl-acetamide / 4 h / 160 °C
2: 72 percent / OsO4, NMO, H2O / acetone; 2-methyl-propan-2-ol / 12 h / Ambient temperature
3: 98 percent / CSA / acetonitrile; CH2Cl2 / 1 h / Ambient temperature
4: OsO4, NMO, aq. NaHCO3, MeSO2NH2 / tetrahydrofuran; 2-methyl-propan-2-ol / 144 h / 40 °C
5: 82 percent / pyridine, NaHCO3, H5IO6 / tetrahydrofuran / 24 h / Ambient temperature
6: 80 percent / LDA / tetrahydrofuran / 1.) -40 to -50 deg C, 30 min, 2.) -75 deg C, 14 h
7: 83 percent / H2, pyridine / 10percent Pd/C / ethanol; tetrahydrofuran / 14 h / 2585.7 Torr / Ambient temperature
8: 99 percent / LAH / tetrahydrofuran / 1.) r.t. 2 h, 2.) reflux, overnight
9: 96 percent / CSA / 24 h / Ambient temperature
10: 91 percent / CrO3, pyridine / CH2Cl2 / 48 h / Ambient temperature
11: 72 percent / <(C6H5)3P>3RhCl / benzene / 5 h / Heating
View Scheme
(22E,24S)-2α,3α-dihydroxy-5α-stigmast-22-en-6-one
81481-12-1

(22E,24S)-2α,3α-dihydroxy-5α-stigmast-22-en-6-one

(3α,5α,6α,8β,9α,12β,13β,16α,17β)-10-[(2'α,3'β,4'β,5'β)-3,4-dihydroxy-5,6-dimethyl-2-heptanyl]-5,6-dihydroxy-7a,9a-dimethylhexadecahydro-3H-benzo[c]indeno[5,4-e]oxepin-3-one
72962-43-7

(3α,5α,6α,8β,9α,12β,13β,16α,17β)-10-[(2'α,3'β,4'β,5'β)-3,4-dihydroxy-5,6-dimethyl-2-heptanyl]-5,6-dihydroxy-7a,9a-dimethylhexadecahydro-3H-benzo[c]indeno[5,4-e]oxepin-3-one

Conditions
ConditionsYield
Multi-step reaction with 10 steps
1: 98 percent / CSA / acetonitrile; CH2Cl2 / 1 h / Ambient temperature
2: OsO4, NMO, aq. NaHCO3, MeSO2NH2 / tetrahydrofuran; 2-methyl-propan-2-ol / 144 h / 40 °C
3: 82 percent / pyridine, NaHCO3, H5IO6 / tetrahydrofuran / 24 h / Ambient temperature
4: 80 percent / LDA / tetrahydrofuran / 1.) -40 to -50 deg C, 30 min, 2.) -75 deg C, 14 h
5: 83 percent / H2, pyridine / 10percent Pd/C / ethanol; tetrahydrofuran / 14 h / 2585.7 Torr / Ambient temperature
6: 99 percent / LAH / tetrahydrofuran / 1.) r.t. 2 h, 2.) reflux, overnight
7: 96 percent / CSA / 24 h / Ambient temperature
8: 91 percent / CrO3, pyridine / CH2Cl2 / 48 h / Ambient temperature
9: 72 percent / <(C6H5)3P>3RhCl / benzene / 5 h / Heating
View Scheme
(22E,24S)-2α,3α-Dihydroxy-5α-stigmast-22-en-6-one 2,3-acetonide
81481-13-2

(22E,24S)-2α,3α-Dihydroxy-5α-stigmast-22-en-6-one 2,3-acetonide

(3α,5α,6α,8β,9α,12β,13β,16α,17β)-10-[(2'α,3'β,4'β,5'β)-3,4-dihydroxy-5,6-dimethyl-2-heptanyl]-5,6-dihydroxy-7a,9a-dimethylhexadecahydro-3H-benzo[c]indeno[5,4-e]oxepin-3-one
72962-43-7

(3α,5α,6α,8β,9α,12β,13β,16α,17β)-10-[(2'α,3'β,4'β,5'β)-3,4-dihydroxy-5,6-dimethyl-2-heptanyl]-5,6-dihydroxy-7a,9a-dimethylhexadecahydro-3H-benzo[c]indeno[5,4-e]oxepin-3-one

Conditions
ConditionsYield
Multi-step reaction with 9 steps
1: OsO4, NMO, aq. NaHCO3, MeSO2NH2 / tetrahydrofuran; 2-methyl-propan-2-ol / 144 h / 40 °C
2: 82 percent / pyridine, NaHCO3, H5IO6 / tetrahydrofuran / 24 h / Ambient temperature
3: 80 percent / LDA / tetrahydrofuran / 1.) -40 to -50 deg C, 30 min, 2.) -75 deg C, 14 h
4: 83 percent / H2, pyridine / 10percent Pd/C / ethanol; tetrahydrofuran / 14 h / 2585.7 Torr / Ambient temperature
5: 99 percent / LAH / tetrahydrofuran / 1.) r.t. 2 h, 2.) reflux, overnight
6: 96 percent / CSA / 24 h / Ambient temperature
7: 91 percent / CrO3, pyridine / CH2Cl2 / 48 h / Ambient temperature
8: 72 percent / <(C6H5)3P>3RhCl / benzene / 5 h / Heating
View Scheme
Multi-step reaction with 10 steps
1: 83.0 g / p-TsOH / 3 h / Heating
2: 30 g / ozone, NaHCO3 / methanol; CH2Cl2 / 2 h / -60 - -50 °C
3: n-BuLi / tetrahydrofuran; hexane / -50 to -60 deg C; -40 deg C, 1 h; -68 to - 65 deg C, 1 h; 0 deg C
4: 74.6 percent / 1.) triphenylphosphine, benzoic acid, diethyl azodicarboxylate; 2.) K2CO3 / 1.) THF, 5-10 deg C, 30 min; 2.) THF/methanol, reflux, 3 h
5: 44.3 g / H2, 1M NaBH4, ethylenediamine, nickel acetate / aq. ethanol / 5 h
6: 93 percent / m-chloroperbenzoic acid, Na2HPO4 / CH2Cl2 / 20 h / 5 °C
7: n-BuLi / hexane; cyclohexane / -70 deg C, 1 h; 10 deg C, 4 h
8: 7.62 g / 80percent AcOH / H2O / 1 h / 50 - 60 °C
9: pyridine, N,N-dimethylaminopyridine
View Scheme
Multi-step reaction with 9 steps
1: 83.0 g / p-TsOH / 3 h / Heating
2: 30 g / ozone, NaHCO3 / methanol; CH2Cl2 / 2 h / -60 - -50 °C
3: 26.93 g / n-BuLi / tetrahydrofuran; hexane / -50 to -60 deg C; -40 deg C, 1 h; -68 to - 65 deg C, 1 h; 0 deg C
4: 44.3 g / H2, 1M NaBH4, ethylenediamine, nickel acetate / aq. ethanol / 5 h
5: 93 percent / m-chloroperbenzoic acid, Na2HPO4 / CH2Cl2 / 20 h / 5 °C
6: n-BuLi / hexane; cyclohexane / -70 deg C, 1 h; 10 deg C, 4 h
7: 7.62 g / 80percent AcOH / H2O / 1 h / 50 - 60 °C
8: pyridine, N,N-dimethylaminopyridine
View Scheme
(22E,24S)-24-ethyl-3α,5-cyclo-5α-cholest-22-en-6-ol
103881-47-6

(22E,24S)-24-ethyl-3α,5-cyclo-5α-cholest-22-en-6-ol

(3α,5α,6α,8β,9α,12β,13β,16α,17β)-10-[(2'α,3'β,4'β,5'β)-3,4-dihydroxy-5,6-dimethyl-2-heptanyl]-5,6-dihydroxy-7a,9a-dimethylhexadecahydro-3H-benzo[c]indeno[5,4-e]oxepin-3-one
72962-43-7

(3α,5α,6α,8β,9α,12β,13β,16α,17β)-10-[(2'α,3'β,4'β,5'β)-3,4-dihydroxy-5,6-dimethyl-2-heptanyl]-5,6-dihydroxy-7a,9a-dimethylhexadecahydro-3H-benzo[c]indeno[5,4-e]oxepin-3-one

Conditions
ConditionsYield
Multi-step reaction with 13 steps
1: CrO3, H2SO4 / acetone
2: 80 percent / pyridine hydrochloride, LiBr / N,N-dimethyl-acetamide / 4 h / 160 °C
3: 72 percent / OsO4, NMO, H2O / acetone; 2-methyl-propan-2-ol / 12 h / Ambient temperature
4: 98 percent / CSA / acetonitrile; CH2Cl2 / 1 h / Ambient temperature
5: OsO4, NMO, aq. NaHCO3, MeSO2NH2 / tetrahydrofuran; 2-methyl-propan-2-ol / 144 h / 40 °C
6: 82 percent / pyridine, NaHCO3, H5IO6 / tetrahydrofuran / 24 h / Ambient temperature
7: 80 percent / LDA / tetrahydrofuran / 1.) -40 to -50 deg C, 30 min, 2.) -75 deg C, 14 h
8: 83 percent / H2, pyridine / 10percent Pd/C / ethanol; tetrahydrofuran / 14 h / 2585.7 Torr / Ambient temperature
9: 99 percent / LAH / tetrahydrofuran / 1.) r.t. 2 h, 2.) reflux, overnight
10: 96 percent / CSA / 24 h / Ambient temperature
11: 91 percent / CrO3, pyridine / CH2Cl2 / 48 h / Ambient temperature
12: 72 percent / <(C6H5)3P>3RhCl / benzene / 5 h / Heating
View Scheme
1-bromo-3-methyl-2-butanone
19967-55-6

1-bromo-3-methyl-2-butanone

(3α,5α,6α,8β,9α,12β,13β,16α,17β)-10-[(2'α,3'β,4'β,5'β)-3,4-dihydroxy-5,6-dimethyl-2-heptanyl]-5,6-dihydroxy-7a,9a-dimethylhexadecahydro-3H-benzo[c]indeno[5,4-e]oxepin-3-one
72962-43-7

(3α,5α,6α,8β,9α,12β,13β,16α,17β)-10-[(2'α,3'β,4'β,5'β)-3,4-dihydroxy-5,6-dimethyl-2-heptanyl]-5,6-dihydroxy-7a,9a-dimethylhexadecahydro-3H-benzo[c]indeno[5,4-e]oxepin-3-one

Conditions
ConditionsYield
Multi-step reaction with 9 steps
1: acetone / 18 h / Heating
2: NaH / tetrahydrofuran / 0.5 h / 25 °C
3: 80 percent / LDA / tetrahydrofuran / 1.) -40 to -50 deg C, 30 min, 2.) -75 deg C, 14 h
4: 83 percent / H2, pyridine / 10percent Pd/C / ethanol; tetrahydrofuran / 14 h / 2585.7 Torr / Ambient temperature
5: 99 percent / LAH / tetrahydrofuran / 1.) r.t. 2 h, 2.) reflux, overnight
6: 96 percent / CSA / 24 h / Ambient temperature
7: 91 percent / CrO3, pyridine / CH2Cl2 / 48 h / Ambient temperature
8: 72 percent / <(C6H5)3P>3RhCl / benzene / 5 h / Heating
View Scheme
Multi-step reaction with 9 steps
1: acetone / 18 h / Heating
2: 1.) NaH, triethylphosphonoacetate, 2.) aq. KOH / 1.) THF, 25 deg C, 30 min, 2.) 25 deg C, 24 h
3: 80 percent / LDA / tetrahydrofuran / 1.) -40 to -50 deg C, 30 min, 2.) -75 deg C, 14 h
4: 83 percent / H2, pyridine / 10percent Pd/C / ethanol; tetrahydrofuran / 14 h / 2585.7 Torr / Ambient temperature
5: 99 percent / LAH / tetrahydrofuran / 1.) r.t. 2 h, 2.) reflux, overnight
6: 96 percent / CSA / 24 h / Ambient temperature
7: 91 percent / CrO3, pyridine / CH2Cl2 / 48 h / Ambient temperature
8: 72 percent / <(C6H5)3P>3RhCl / benzene / 5 h / Heating
View Scheme
(20S)-2α,3α-isopropylidenedioxy-5α-pregnan-6-one-20-carbaldehyde
174656-33-8

(20S)-2α,3α-isopropylidenedioxy-5α-pregnan-6-one-20-carbaldehyde

(3α,5α,6α,8β,9α,12β,13β,16α,17β)-10-[(2'α,3'β,4'β,5'β)-3,4-dihydroxy-5,6-dimethyl-2-heptanyl]-5,6-dihydroxy-7a,9a-dimethylhexadecahydro-3H-benzo[c]indeno[5,4-e]oxepin-3-one
72962-43-7

(3α,5α,6α,8β,9α,12β,13β,16α,17β)-10-[(2'α,3'β,4'β,5'β)-3,4-dihydroxy-5,6-dimethyl-2-heptanyl]-5,6-dihydroxy-7a,9a-dimethylhexadecahydro-3H-benzo[c]indeno[5,4-e]oxepin-3-one

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1: 80 percent / LDA / tetrahydrofuran / 1.) -40 to -50 deg C, 30 min, 2.) -75 deg C, 14 h
2: 83 percent / H2, pyridine / 10percent Pd/C / ethanol; tetrahydrofuran / 14 h / 2585.7 Torr / Ambient temperature
3: 99 percent / LAH / tetrahydrofuran / 1.) r.t. 2 h, 2.) reflux, overnight
4: 96 percent / CSA / 24 h / Ambient temperature
5: 91 percent / CrO3, pyridine / CH2Cl2 / 48 h / Ambient temperature
6: 72 percent / <(C6H5)3P>3RhCl / benzene / 5 h / Heating
View Scheme
(3S,4R,5R,6S)-6-((1R,3aS,3bS,5aS,6aS,9aR,10aR,10bS,12aS)-5-Hydroxy-8,8,10a,12a-tetramethyl-hexadecahydro-7,9-dioxa-dicyclopenta[a,h]phenanthren-1-yl)-3-isopropyl-heptane-1,4,5-triol

(3S,4R,5R,6S)-6-((1R,3aS,3bS,5aS,6aS,9aR,10aR,10bS,12aS)-5-Hydroxy-8,8,10a,12a-tetramethyl-hexadecahydro-7,9-dioxa-dicyclopenta[a,h]phenanthren-1-yl)-3-isopropyl-heptane-1,4,5-triol

(3α,5α,6α,8β,9α,12β,13β,16α,17β)-10-[(2'α,3'β,4'β,5'β)-3,4-dihydroxy-5,6-dimethyl-2-heptanyl]-5,6-dihydroxy-7a,9a-dimethylhexadecahydro-3H-benzo[c]indeno[5,4-e]oxepin-3-one
72962-43-7

(3α,5α,6α,8β,9α,12β,13β,16α,17β)-10-[(2'α,3'β,4'β,5'β)-3,4-dihydroxy-5,6-dimethyl-2-heptanyl]-5,6-dihydroxy-7a,9a-dimethylhexadecahydro-3H-benzo[c]indeno[5,4-e]oxepin-3-one

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 96 percent / CSA / 24 h / Ambient temperature
2: 91 percent / CrO3, pyridine / CH2Cl2 / 48 h / Ambient temperature
3: 72 percent / <(C6H5)3P>3RhCl / benzene / 5 h / Heating
View Scheme
(1R,3aS,3bS,5aS,6aS,9aR,10aR,10bS,12aS)-1-((S)-1-{(4R,5R)-5-[(S)-1-(2-Hydroxy-ethyl)-2-methyl-propyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-ethyl)-8,8,10a,12a-tetramethyl-hexadecahydro-7,9-dioxa-dicyclopenta[a,h]phenanthren-5-ol

(1R,3aS,3bS,5aS,6aS,9aR,10aR,10bS,12aS)-1-((S)-1-{(4R,5R)-5-[(S)-1-(2-Hydroxy-ethyl)-2-methyl-propyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-ethyl)-8,8,10a,12a-tetramethyl-hexadecahydro-7,9-dioxa-dicyclopenta[a,h]phenanthren-5-ol

(3α,5α,6α,8β,9α,12β,13β,16α,17β)-10-[(2'α,3'β,4'β,5'β)-3,4-dihydroxy-5,6-dimethyl-2-heptanyl]-5,6-dihydroxy-7a,9a-dimethylhexadecahydro-3H-benzo[c]indeno[5,4-e]oxepin-3-one
72962-43-7

(3α,5α,6α,8β,9α,12β,13β,16α,17β)-10-[(2'α,3'β,4'β,5'β)-3,4-dihydroxy-5,6-dimethyl-2-heptanyl]-5,6-dihydroxy-7a,9a-dimethylhexadecahydro-3H-benzo[c]indeno[5,4-e]oxepin-3-one

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 91 percent / CrO3, pyridine / CH2Cl2 / 48 h / Ambient temperature
2: 72 percent / <(C6H5)3P>3RhCl / benzene / 5 h / Heating
View Scheme
(S)-3-{(4R,5R)-2,2-Dimethyl-5-[(S)-1-((1R,3aS,3bS,5aS,6aS,9aR,10aR,10bS,12aS)-8,8,10a,12a-tetramethyl-5-oxo-hexadecahydro-7,9-dioxa-dicyclopenta[a,h]phenanthren-1-yl)-ethyl]-[1,3]dioxolan-4-yl}-4-methyl-pentanal
174656-38-3

(S)-3-{(4R,5R)-2,2-Dimethyl-5-[(S)-1-((1R,3aS,3bS,5aS,6aS,9aR,10aR,10bS,12aS)-8,8,10a,12a-tetramethyl-5-oxo-hexadecahydro-7,9-dioxa-dicyclopenta[a,h]phenanthren-1-yl)-ethyl]-[1,3]dioxolan-4-yl}-4-methyl-pentanal

(3α,5α,6α,8β,9α,12β,13β,16α,17β)-10-[(2'α,3'β,4'β,5'β)-3,4-dihydroxy-5,6-dimethyl-2-heptanyl]-5,6-dihydroxy-7a,9a-dimethylhexadecahydro-3H-benzo[c]indeno[5,4-e]oxepin-3-one
72962-43-7

(3α,5α,6α,8β,9α,12β,13β,16α,17β)-10-[(2'α,3'β,4'β,5'β)-3,4-dihydroxy-5,6-dimethyl-2-heptanyl]-5,6-dihydroxy-7a,9a-dimethylhexadecahydro-3H-benzo[c]indeno[5,4-e]oxepin-3-one

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 72 percent / <(C6H5)3P>3RhCl / benzene / 5 h / Heating
View Scheme
(1R,3aS,3bS,5aS,6aS,9aR,10aR,10bS,12aS)-1-((1S,2S,3S,4S)-4-Ethyl-2,3-dihydroxy-1,5-dimethyl-hexyl)-8,8,10a,12a-tetramethyl-hexadecahydro-7,9-dioxa-dicyclopenta[a,h]phenanthren-5-one
123450-38-4

(1R,3aS,3bS,5aS,6aS,9aR,10aR,10bS,12aS)-1-((1S,2S,3S,4S)-4-Ethyl-2,3-dihydroxy-1,5-dimethyl-hexyl)-8,8,10a,12a-tetramethyl-hexadecahydro-7,9-dioxa-dicyclopenta[a,h]phenanthren-5-one

(3α,5α,6α,8β,9α,12β,13β,16α,17β)-10-[(2'α,3'β,4'β,5'β)-3,4-dihydroxy-5,6-dimethyl-2-heptanyl]-5,6-dihydroxy-7a,9a-dimethylhexadecahydro-3H-benzo[c]indeno[5,4-e]oxepin-3-one
72962-43-7

(3α,5α,6α,8β,9α,12β,13β,16α,17β)-10-[(2'α,3'β,4'β,5'β)-3,4-dihydroxy-5,6-dimethyl-2-heptanyl]-5,6-dihydroxy-7a,9a-dimethylhexadecahydro-3H-benzo[c]indeno[5,4-e]oxepin-3-one

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1: 82 percent / pyridine, NaHCO3, H5IO6 / tetrahydrofuran / 24 h / Ambient temperature
2: 80 percent / LDA / tetrahydrofuran / 1.) -40 to -50 deg C, 30 min, 2.) -75 deg C, 14 h
3: 83 percent / H2, pyridine / 10percent Pd/C / ethanol; tetrahydrofuran / 14 h / 2585.7 Torr / Ambient temperature
4: 99 percent / LAH / tetrahydrofuran / 1.) r.t. 2 h, 2.) reflux, overnight
5: 96 percent / CSA / 24 h / Ambient temperature
6: 91 percent / CrO3, pyridine / CH2Cl2 / 48 h / Ambient temperature
7: 72 percent / <(C6H5)3P>3RhCl / benzene / 5 h / Heating
View Scheme
(1R,3aS,3bS,5aS,6aS,9aR,10aR,10bS,12aS)-1-[(1S,2R)-2-Hydroxy-2-((2R,3S)-3-isopropyl-5-oxo-tetrahydro-furan-2-yl)-1-methyl-ethyl]-8,8,10a,12a-tetramethyl-hexadecahydro-7,9-dioxa-dicyclopenta[a,h]phenanthren-5-one
174656-35-0

(1R,3aS,3bS,5aS,6aS,9aR,10aR,10bS,12aS)-1-[(1S,2R)-2-Hydroxy-2-((2R,3S)-3-isopropyl-5-oxo-tetrahydro-furan-2-yl)-1-methyl-ethyl]-8,8,10a,12a-tetramethyl-hexadecahydro-7,9-dioxa-dicyclopenta[a,h]phenanthren-5-one

(3α,5α,6α,8β,9α,12β,13β,16α,17β)-10-[(2'α,3'β,4'β,5'β)-3,4-dihydroxy-5,6-dimethyl-2-heptanyl]-5,6-dihydroxy-7a,9a-dimethylhexadecahydro-3H-benzo[c]indeno[5,4-e]oxepin-3-one
72962-43-7

(3α,5α,6α,8β,9α,12β,13β,16α,17β)-10-[(2'α,3'β,4'β,5'β)-3,4-dihydroxy-5,6-dimethyl-2-heptanyl]-5,6-dihydroxy-7a,9a-dimethylhexadecahydro-3H-benzo[c]indeno[5,4-e]oxepin-3-one

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 99 percent / LAH / tetrahydrofuran / 1.) r.t. 2 h, 2.) reflux, overnight
2: 96 percent / CSA / 24 h / Ambient temperature
3: 91 percent / CrO3, pyridine / CH2Cl2 / 48 h / Ambient temperature
4: 72 percent / <(C6H5)3P>3RhCl / benzene / 5 h / Heating
View Scheme
(1R,3aS,3bS,5aS,6aS,9aR,10aR,10bS,12aS)-1-[(1S,2R)-2-Hydroxy-2-((R)-3-isopropyl-5-oxo-2,5-dihydro-furan-2-yl)-1-methyl-ethyl]-8,8,10a,12a-tetramethyl-hexadecahydro-7,9-dioxa-dicyclopenta[a,h]phenanthren-5-one
174656-34-9

(1R,3aS,3bS,5aS,6aS,9aR,10aR,10bS,12aS)-1-[(1S,2R)-2-Hydroxy-2-((R)-3-isopropyl-5-oxo-2,5-dihydro-furan-2-yl)-1-methyl-ethyl]-8,8,10a,12a-tetramethyl-hexadecahydro-7,9-dioxa-dicyclopenta[a,h]phenanthren-5-one

(3α,5α,6α,8β,9α,12β,13β,16α,17β)-10-[(2'α,3'β,4'β,5'β)-3,4-dihydroxy-5,6-dimethyl-2-heptanyl]-5,6-dihydroxy-7a,9a-dimethylhexadecahydro-3H-benzo[c]indeno[5,4-e]oxepin-3-one
72962-43-7

(3α,5α,6α,8β,9α,12β,13β,16α,17β)-10-[(2'α,3'β,4'β,5'β)-3,4-dihydroxy-5,6-dimethyl-2-heptanyl]-5,6-dihydroxy-7a,9a-dimethylhexadecahydro-3H-benzo[c]indeno[5,4-e]oxepin-3-one

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: 83 percent / H2, pyridine / 10percent Pd/C / ethanol; tetrahydrofuran / 14 h / 2585.7 Torr / Ambient temperature
2: 99 percent / LAH / tetrahydrofuran / 1.) r.t. 2 h, 2.) reflux, overnight
3: 96 percent / CSA / 24 h / Ambient temperature
4: 91 percent / CrO3, pyridine / CH2Cl2 / 48 h / Ambient temperature
5: 72 percent / <(C6H5)3P>3RhCl / benzene / 5 h / Heating
View Scheme
6,6-ethylenedioxy-2α,3α-isopropylidenedioxy-24S-ethyl-5α-cholest-22E-ene
81481-14-3

6,6-ethylenedioxy-2α,3α-isopropylidenedioxy-24S-ethyl-5α-cholest-22E-ene

(3α,5α,6α,8β,9α,12β,13β,16α,17β)-10-[(2'α,3'β,4'β,5'β)-3,4-dihydroxy-5,6-dimethyl-2-heptanyl]-5,6-dihydroxy-7a,9a-dimethylhexadecahydro-3H-benzo[c]indeno[5,4-e]oxepin-3-one
72962-43-7

(3α,5α,6α,8β,9α,12β,13β,16α,17β)-10-[(2'α,3'β,4'β,5'β)-3,4-dihydroxy-5,6-dimethyl-2-heptanyl]-5,6-dihydroxy-7a,9a-dimethylhexadecahydro-3H-benzo[c]indeno[5,4-e]oxepin-3-one

Conditions
ConditionsYield
Multi-step reaction with 9 steps
1: 30 g / ozone, NaHCO3 / methanol; CH2Cl2 / 2 h / -60 - -50 °C
2: n-BuLi / tetrahydrofuran; hexane / -50 to -60 deg C; -40 deg C, 1 h; -68 to - 65 deg C, 1 h; 0 deg C
3: 74.6 percent / 1.) triphenylphosphine, benzoic acid, diethyl azodicarboxylate; 2.) K2CO3 / 1.) THF, 5-10 deg C, 30 min; 2.) THF/methanol, reflux, 3 h
4: 44.3 g / H2, 1M NaBH4, ethylenediamine, nickel acetate / aq. ethanol / 5 h
5: 93 percent / m-chloroperbenzoic acid, Na2HPO4 / CH2Cl2 / 20 h / 5 °C
6: n-BuLi / hexane; cyclohexane / -70 deg C, 1 h; 10 deg C, 4 h
7: 7.62 g / 80percent AcOH / H2O / 1 h / 50 - 60 °C
8: pyridine, N,N-dimethylaminopyridine
View Scheme
Multi-step reaction with 8 steps
1: 30 g / ozone, NaHCO3 / methanol; CH2Cl2 / 2 h / -60 - -50 °C
2: 26.93 g / n-BuLi / tetrahydrofuran; hexane / -50 to -60 deg C; -40 deg C, 1 h; -68 to - 65 deg C, 1 h; 0 deg C
3: 44.3 g / H2, 1M NaBH4, ethylenediamine, nickel acetate / aq. ethanol / 5 h
4: 93 percent / m-chloroperbenzoic acid, Na2HPO4 / CH2Cl2 / 20 h / 5 °C
5: n-BuLi / hexane; cyclohexane / -70 deg C, 1 h; 10 deg C, 4 h
6: 7.62 g / 80percent AcOH / H2O / 1 h / 50 - 60 °C
7: pyridine, N,N-dimethylaminopyridine
View Scheme
(2R, 3S, 22R, 23S, 24R)-23,24-epoxy-6,6-ethylenedioxy-22-hydroxy-2,3-isopropylidenedioxy-5α-cholestane
86413-56-1

(2R, 3S, 22R, 23S, 24R)-23,24-epoxy-6,6-ethylenedioxy-22-hydroxy-2,3-isopropylidenedioxy-5α-cholestane

(3α,5α,6α,8β,9α,12β,13β,16α,17β)-10-[(2'α,3'β,4'β,5'β)-3,4-dihydroxy-5,6-dimethyl-2-heptanyl]-5,6-dihydroxy-7a,9a-dimethylhexadecahydro-3H-benzo[c]indeno[5,4-e]oxepin-3-one
72962-43-7

(3α,5α,6α,8β,9α,12β,13β,16α,17β)-10-[(2'α,3'β,4'β,5'β)-3,4-dihydroxy-5,6-dimethyl-2-heptanyl]-5,6-dihydroxy-7a,9a-dimethylhexadecahydro-3H-benzo[c]indeno[5,4-e]oxepin-3-one

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: n-BuLi / hexane; cyclohexane / -70 deg C, 1 h; 10 deg C, 4 h
2: 7.62 g / 80percent AcOH / H2O / 1 h / 50 - 60 °C
3: pyridine, N,N-dimethylaminopyridine
View Scheme
(3α,5α,6α,8β,9α,12β,13β,16α,17β)-10-[(2'α,3'β,4'β,5'β)-3,4-dihydroxy-5,6-dimethyl-2-heptanyl]-5,6-dihydroxy-7a,9a-dimethylhexadecahydro-3H-benzo[c]indeno[5,4-e]oxepin-3-one
72962-43-7

(3α,5α,6α,8β,9α,12β,13β,16α,17β)-10-[(2'α,3'β,4'β,5'β)-3,4-dihydroxy-5,6-dimethyl-2-heptanyl]-5,6-dihydroxy-7a,9a-dimethylhexadecahydro-3H-benzo[c]indeno[5,4-e]oxepin-3-one

acetic anhydride
108-24-7

acetic anhydride

2α,3α-22R,23R-tetraacetoxy-B-homo-7-oxa-24S-methyl-5α-cholestan-6-one
76987-58-1

2α,3α-22R,23R-tetraacetoxy-B-homo-7-oxa-24S-methyl-5α-cholestan-6-one

Conditions
ConditionsYield
With pyridine at 60℃; for 20h; Acetylation;95%
(3α,5α,6α,8β,9α,12β,13β,16α,17β)-10-[(2'α,3'β,4'β,5'β)-3,4-dihydroxy-5,6-dimethyl-2-heptanyl]-5,6-dihydroxy-7a,9a-dimethylhexadecahydro-3H-benzo[c]indeno[5,4-e]oxepin-3-one
72962-43-7

(3α,5α,6α,8β,9α,12β,13β,16α,17β)-10-[(2'α,3'β,4'β,5'β)-3,4-dihydroxy-5,6-dimethyl-2-heptanyl]-5,6-dihydroxy-7a,9a-dimethylhexadecahydro-3H-benzo[c]indeno[5,4-e]oxepin-3-one

acetone
67-64-1

acetone

C34H56O6
220399-01-9

C34H56O6

Conditions
ConditionsYield
With toluene-4-sulfonic acid for 8h; Ambient temperature;91%
(3α,5α,6α,8β,9α,12β,13β,16α,17β)-10-[(2'α,3'β,4'β,5'β)-3,4-dihydroxy-5,6-dimethyl-2-heptanyl]-5,6-dihydroxy-7a,9a-dimethylhexadecahydro-3H-benzo[c]indeno[5,4-e]oxepin-3-one
72962-43-7

(3α,5α,6α,8β,9α,12β,13β,16α,17β)-10-[(2'α,3'β,4'β,5'β)-3,4-dihydroxy-5,6-dimethyl-2-heptanyl]-5,6-dihydroxy-7a,9a-dimethylhexadecahydro-3H-benzo[c]indeno[5,4-e]oxepin-3-one

2,2-dimethoxy-propane
77-76-9

2,2-dimethoxy-propane

C34H56O6

C34H56O6

Conditions
ConditionsYield
With toluene-4-sulfonic acid In dichloromethane Ambient temperature;82%
(3α,5α,6α,8β,9α,12β,13β,16α,17β)-10-[(2'α,3'β,4'β,5'β)-3,4-dihydroxy-5,6-dimethyl-2-heptanyl]-5,6-dihydroxy-7a,9a-dimethylhexadecahydro-3H-benzo[c]indeno[5,4-e]oxepin-3-one
72962-43-7

(3α,5α,6α,8β,9α,12β,13β,16α,17β)-10-[(2'α,3'β,4'β,5'β)-3,4-dihydroxy-5,6-dimethyl-2-heptanyl]-5,6-dihydroxy-7a,9a-dimethylhexadecahydro-3H-benzo[c]indeno[5,4-e]oxepin-3-one

A

Brassinolide

Brassinolide

B

(1R,2R,4R,5S)-2-[(1R,3aS,4S,5S,7aS)-1-((1S,2R,3R,4S)-2,3-Dihydroxy-1,4,5-trimethyl-hexyl)-4-hydroxymethyl-7a-methyl-octahydro-inden-5-yl]-4-hydroxy-2-methyl-6-oxa-bicyclo[3.2.1]octan-7-one

(1R,2R,4R,5S)-2-[(1R,3aS,4S,5S,7aS)-1-((1S,2R,3R,4S)-2,3-Dihydroxy-1,4,5-trimethyl-hexyl)-4-hydroxymethyl-7a-methyl-octahydro-inden-5-yl]-4-hydroxy-2-methyl-6-oxa-bicyclo[3.2.1]octan-7-one

Conditions
ConditionsYield
With methanol; Dowex 50W resin (H(1+)-form); water; sodium methylate 1.) reflux, 5 h, 2.) MeOH, r.t., 3 h; Yield given. Multistep reaction. Yields of byproduct given;
(3α,5α,6α,8β,9α,12β,13β,16α,17β)-10-[(2'α,3'β,4'β,5'β)-3,4-dihydroxy-5,6-dimethyl-2-heptanyl]-5,6-dihydroxy-7a,9a-dimethylhexadecahydro-3H-benzo[c]indeno[5,4-e]oxepin-3-one
72962-43-7

(3α,5α,6α,8β,9α,12β,13β,16α,17β)-10-[(2'α,3'β,4'β,5'β)-3,4-dihydroxy-5,6-dimethyl-2-heptanyl]-5,6-dihydroxy-7a,9a-dimethylhexadecahydro-3H-benzo[c]indeno[5,4-e]oxepin-3-one

2,3,22,33-tetra-O-acetyl-25-hydroxybrassinolide
180961-17-5

2,3,22,33-tetra-O-acetyl-25-hydroxybrassinolide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 95 percent / pyridine / 20 h / 60 °C
2: 61 percent / methyl(trifluoromethyl)dioxirane; 1,1,1-trifluoroacetone / CH2Cl2 / 5 h / -30 °C
View Scheme
Multi-step reaction with 2 steps
1: 95 percent / pyridine / 20 h / 60 °C
2: 48 percent / methyl(trifluoromethyl)dioxirane; 1,1,1-trifluoroacetone / CH2Cl2 / 3 h / 0 °C
View Scheme
(3α,5α,6α,8β,9α,12β,13β,16α,17β)-10-[(2'α,3'β,4'β,5'β)-3,4-dihydroxy-5,6-dimethyl-2-heptanyl]-5,6-dihydroxy-7a,9a-dimethylhexadecahydro-3H-benzo[c]indeno[5,4-e]oxepin-3-one
72962-43-7

(3α,5α,6α,8β,9α,12β,13β,16α,17β)-10-[(2'α,3'β,4'β,5'β)-3,4-dihydroxy-5,6-dimethyl-2-heptanyl]-5,6-dihydroxy-7a,9a-dimethylhexadecahydro-3H-benzo[c]indeno[5,4-e]oxepin-3-one

25-hydroxybrassinolide

25-hydroxybrassinolide

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 95 percent / pyridine / 20 h / 60 °C
2: 61 percent / methyl(trifluoromethyl)dioxirane; 1,1,1-trifluoroacetone / CH2Cl2 / 5 h / -30 °C
3: 86 percent / KOH / methanol; H2O / 1 h / 20 °C
View Scheme
Multi-step reaction with 3 steps
1: 95 percent / pyridine / 20 h / 60 °C
2: 61 percent / methyl(trifluoromethyl)dioxirane; 1,1,1-trifluoroacetone / CH2Cl2 / 5 h / -30 °C
3: 56 percent / KOH / methanol; H2O / 3 h / Heating
View Scheme
Multi-step reaction with 3 steps
1: 95 percent / pyridine / 20 h / 60 °C
2: 48 percent / methyl(trifluoromethyl)dioxirane; 1,1,1-trifluoroacetone / CH2Cl2 / 3 h / 0 °C
3: 86 percent / KOH / methanol; H2O / 1 h / 20 °C
View Scheme
Multi-step reaction with 3 steps
1: 95 percent / pyridine / 20 h / 60 °C
2: 48 percent / methyl(trifluoromethyl)dioxirane; 1,1,1-trifluoroacetone / CH2Cl2 / 3 h / 0 °C
3: 56 percent / KOH / methanol; H2O / 3 h / Heating
View Scheme
(3α,5α,6α,8β,9α,12β,13β,16α,17β)-10-[(2'α,3'β,4'β,5'β)-3,4-dihydroxy-5,6-dimethyl-2-heptanyl]-5,6-dihydroxy-7a,9a-dimethylhexadecahydro-3H-benzo[c]indeno[5,4-e]oxepin-3-one
72962-43-7

(3α,5α,6α,8β,9α,12β,13β,16α,17β)-10-[(2'α,3'β,4'β,5'β)-3,4-dihydroxy-5,6-dimethyl-2-heptanyl]-5,6-dihydroxy-7a,9a-dimethylhexadecahydro-3H-benzo[c]indeno[5,4-e]oxepin-3-one

14α-hydroxybrassinolide

14α-hydroxybrassinolide

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 95 percent / pyridine / 20 h / 60 °C
2: 6.5 percent / methyl(trifluoromethyl)dioxirane; 1,1,1-trifluoroacetone / CH2Cl2 / 3 h / 0 °C
3: 82 percent / KOH / methanol; H2O / 1 h / 20 °C
View Scheme
(3α,5α,6α,8β,9α,12β,13β,16α,17β)-10-[(2'α,3'β,4'β,5'β)-3,4-dihydroxy-5,6-dimethyl-2-heptanyl]-5,6-dihydroxy-7a,9a-dimethylhexadecahydro-3H-benzo[c]indeno[5,4-e]oxepin-3-one
72962-43-7

(3α,5α,6α,8β,9α,12β,13β,16α,17β)-10-[(2'α,3'β,4'β,5'β)-3,4-dihydroxy-5,6-dimethyl-2-heptanyl]-5,6-dihydroxy-7a,9a-dimethylhexadecahydro-3H-benzo[c]indeno[5,4-e]oxepin-3-one

25-hydroxy-6(6α->3a)abeo-5-epi-brassinolide

25-hydroxy-6(6α->3a)abeo-5-epi-brassinolide

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 95 percent / pyridine / 20 h / 60 °C
2: 61 percent / methyl(trifluoromethyl)dioxirane; 1,1,1-trifluoroacetone / CH2Cl2 / 5 h / -30 °C
3: 12 percent / KOH / methanol; H2O / 3 h / Heating
View Scheme
Multi-step reaction with 3 steps
1: 95 percent / pyridine / 20 h / 60 °C
2: 48 percent / methyl(trifluoromethyl)dioxirane; 1,1,1-trifluoroacetone / CH2Cl2 / 3 h / 0 °C
3: 12 percent / KOH / methanol; H2O / 3 h / Heating
View Scheme
(3α,5α,6α,8β,9α,12β,13β,16α,17β)-10-[(2'α,3'β,4'β,5'β)-3,4-dihydroxy-5,6-dimethyl-2-heptanyl]-5,6-dihydroxy-7a,9a-dimethylhexadecahydro-3H-benzo[c]indeno[5,4-e]oxepin-3-one
72962-43-7

(3α,5α,6α,8β,9α,12β,13β,16α,17β)-10-[(2'α,3'β,4'β,5'β)-3,4-dihydroxy-5,6-dimethyl-2-heptanyl]-5,6-dihydroxy-7a,9a-dimethylhexadecahydro-3H-benzo[c]indeno[5,4-e]oxepin-3-one

5-epi-25-hydroxybrassinolide

5-epi-25-hydroxybrassinolide

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 95 percent / pyridine / 20 h / 60 °C
2: 61 percent / methyl(trifluoromethyl)dioxirane; 1,1,1-trifluoroacetone / CH2Cl2 / 5 h / -30 °C
3: 22 percent / KOH / methanol; H2O / 3 h / Heating
View Scheme
Multi-step reaction with 3 steps
1: 95 percent / pyridine / 20 h / 60 °C
2: 48 percent / methyl(trifluoromethyl)dioxirane; 1,1,1-trifluoroacetone / CH2Cl2 / 3 h / 0 °C
3: 22 percent / KOH / methanol; H2O / 3 h / Heating
View Scheme
(3α,5α,6α,8β,9α,12β,13β,16α,17β)-10-[(2'α,3'β,4'β,5'β)-3,4-dihydroxy-5,6-dimethyl-2-heptanyl]-5,6-dihydroxy-7a,9a-dimethylhexadecahydro-3H-benzo[c]indeno[5,4-e]oxepin-3-one
72962-43-7

(3α,5α,6α,8β,9α,12β,13β,16α,17β)-10-[(2'α,3'β,4'β,5'β)-3,4-dihydroxy-5,6-dimethyl-2-heptanyl]-5,6-dihydroxy-7a,9a-dimethylhexadecahydro-3H-benzo[c]indeno[5,4-e]oxepin-3-one

14α,25-dihydroxybrassinolide

14α,25-dihydroxybrassinolide

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 95 percent / pyridine / 20 h / 60 °C
2: 18 percent / methyl(trifluoromethyl)dioxirane; 1,1,1-trifluoroacetone / CH2Cl2 / 3 h / 0 °C
3: 79 percent / KOH / methanol; H2O / 1 h / 20 °C
View Scheme
Multi-step reaction with 3 steps
1: 95 percent / pyridine / 20 h / 60 °C
2: 78 percent / methyl(trifluoromethyl)dioxirane; 1,1,1-trifluoroacetone / CH2Cl2 / 24 h / 20 °C
3: 79 percent / KOH / methanol; H2O / 1 h / 20 °C
View Scheme
(3α,5α,6α,8β,9α,12β,13β,16α,17β)-10-[(2'α,3'β,4'β,5'β)-3,4-dihydroxy-5,6-dimethyl-2-heptanyl]-5,6-dihydroxy-7a,9a-dimethylhexadecahydro-3H-benzo[c]indeno[5,4-e]oxepin-3-one
72962-43-7

(3α,5α,6α,8β,9α,12β,13β,16α,17β)-10-[(2'α,3'β,4'β,5'β)-3,4-dihydroxy-5,6-dimethyl-2-heptanyl]-5,6-dihydroxy-7a,9a-dimethylhexadecahydro-3H-benzo[c]indeno[5,4-e]oxepin-3-one

2,3,22,33-tetra-O-acetyl-14α-hydroxybrassinolide

2,3,22,33-tetra-O-acetyl-14α-hydroxybrassinolide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 95 percent / pyridine / 20 h / 60 °C
2: 6.5 percent / methyl(trifluoromethyl)dioxirane; 1,1,1-trifluoroacetone / CH2Cl2 / 3 h / 0 °C
View Scheme
(3α,5α,6α,8β,9α,12β,13β,16α,17β)-10-[(2'α,3'β,4'β,5'β)-3,4-dihydroxy-5,6-dimethyl-2-heptanyl]-5,6-dihydroxy-7a,9a-dimethylhexadecahydro-3H-benzo[c]indeno[5,4-e]oxepin-3-one
72962-43-7

(3α,5α,6α,8β,9α,12β,13β,16α,17β)-10-[(2'α,3'β,4'β,5'β)-3,4-dihydroxy-5,6-dimethyl-2-heptanyl]-5,6-dihydroxy-7a,9a-dimethylhexadecahydro-3H-benzo[c]indeno[5,4-e]oxepin-3-one

2,3,22,33-tetra-O-acetyl-25-hydroxy-15-oxo-brassinolide

2,3,22,33-tetra-O-acetyl-25-hydroxy-15-oxo-brassinolide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 95 percent / pyridine / 20 h / 60 °C
2: 3.6 percent / methyl(trifluoromethyl)dioxirane; 1,1,1-trifluoroacetone / CH2Cl2 / 3 h / 0 °C
View Scheme
(3α,5α,6α,8β,9α,12β,13β,16α,17β)-10-[(2'α,3'β,4'β,5'β)-3,4-dihydroxy-5,6-dimethyl-2-heptanyl]-5,6-dihydroxy-7a,9a-dimethylhexadecahydro-3H-benzo[c]indeno[5,4-e]oxepin-3-one
72962-43-7

(3α,5α,6α,8β,9α,12β,13β,16α,17β)-10-[(2'α,3'β,4'β,5'β)-3,4-dihydroxy-5,6-dimethyl-2-heptanyl]-5,6-dihydroxy-7a,9a-dimethylhexadecahydro-3H-benzo[c]indeno[5,4-e]oxepin-3-one

2,3,22,33-tetra-O-acetyl-14α,25-dihydroxybrassinolide
215502-60-6

2,3,22,33-tetra-O-acetyl-14α,25-dihydroxybrassinolide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 95 percent / pyridine / 20 h / 60 °C
2: 18 percent / methyl(trifluoromethyl)dioxirane; 1,1,1-trifluoroacetone / CH2Cl2 / 3 h / 0 °C
View Scheme
Multi-step reaction with 2 steps
1: 95 percent / pyridine / 20 h / 60 °C
2: 78 percent / methyl(trifluoromethyl)dioxirane; 1,1,1-trifluoroacetone / CH2Cl2 / 24 h / 20 °C
View Scheme
(3α,5α,6α,8β,9α,12β,13β,16α,17β)-10-[(2'α,3'β,4'β,5'β)-3,4-dihydroxy-5,6-dimethyl-2-heptanyl]-5,6-dihydroxy-7a,9a-dimethylhexadecahydro-3H-benzo[c]indeno[5,4-e]oxepin-3-one
72962-43-7

(3α,5α,6α,8β,9α,12β,13β,16α,17β)-10-[(2'α,3'β,4'β,5'β)-3,4-dihydroxy-5,6-dimethyl-2-heptanyl]-5,6-dihydroxy-7a,9a-dimethylhexadecahydro-3H-benzo[c]indeno[5,4-e]oxepin-3-one

(22R,23R,24S)-22,23-isopropylidenedioxy-B-homo-7-oxa-5α-ergost-2-en-6-one
220398-86-7

(22R,23R,24S)-22,23-isopropylidenedioxy-B-homo-7-oxa-5α-ergost-2-en-6-one

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 91 percent / p-TsOH / 8 h / Ambient temperature
2: 86 percent / aq. p-TsOH / dioxane / 4 h / 60 °C
3: 4-dimethylaminopyridine / CH2Cl2 / 2 h / 0 °C
4: triethyl phosphite / 5 h / Heating
View Scheme
(3α,5α,6α,8β,9α,12β,13β,16α,17β)-10-[(2'α,3'β,4'β,5'β)-3,4-dihydroxy-5,6-dimethyl-2-heptanyl]-5,6-dihydroxy-7a,9a-dimethylhexadecahydro-3H-benzo[c]indeno[5,4-e]oxepin-3-one
72962-43-7

(3α,5α,6α,8β,9α,12β,13β,16α,17β)-10-[(2'α,3'β,4'β,5'β)-3,4-dihydroxy-5,6-dimethyl-2-heptanyl]-5,6-dihydroxy-7a,9a-dimethylhexadecahydro-3H-benzo[c]indeno[5,4-e]oxepin-3-one

(22R,23R,24S)-2α,3α-epoxy-22,23-isopropylidenedioxy-B-homo-7-oxa-5α-ergostan-6-one
220399-03-1

(22R,23R,24S)-2α,3α-epoxy-22,23-isopropylidenedioxy-B-homo-7-oxa-5α-ergostan-6-one

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 91 percent / p-TsOH / 8 h / Ambient temperature
2: 86 percent / aq. p-TsOH / dioxane / 4 h / 60 °C
3: 4-dimethylaminopyridine / CH2Cl2 / 2 h / 0 °C
4: triethyl phosphite / 5 h / Heating
5: 50 percent / m-CPBA / CH2Cl2 / 2 h / 0 °C
View Scheme
(3α,5α,6α,8β,9α,12β,13β,16α,17β)-10-[(2'α,3'β,4'β,5'β)-3,4-dihydroxy-5,6-dimethyl-2-heptanyl]-5,6-dihydroxy-7a,9a-dimethylhexadecahydro-3H-benzo[c]indeno[5,4-e]oxepin-3-one
72962-43-7

(3α,5α,6α,8β,9α,12β,13β,16α,17β)-10-[(2'α,3'β,4'β,5'β)-3,4-dihydroxy-5,6-dimethyl-2-heptanyl]-5,6-dihydroxy-7a,9a-dimethylhexadecahydro-3H-benzo[c]indeno[5,4-e]oxepin-3-one

(22R,23R,24S)-2α,3α-dihydroxy-22,23-isopropylidenedioxy-B-homo-7-oxa-5α-ergostan-6-one
220398-85-6

(22R,23R,24S)-2α,3α-dihydroxy-22,23-isopropylidenedioxy-B-homo-7-oxa-5α-ergostan-6-one

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 91 percent / p-TsOH / 8 h / Ambient temperature
2: 86 percent / aq. p-TsOH / dioxane / 4 h / 60 °C
View Scheme
(3α,5α,6α,8β,9α,12β,13β,16α,17β)-10-[(2'α,3'β,4'β,5'β)-3,4-dihydroxy-5,6-dimethyl-2-heptanyl]-5,6-dihydroxy-7a,9a-dimethylhexadecahydro-3H-benzo[c]indeno[5,4-e]oxepin-3-one
72962-43-7

(3α,5α,6α,8β,9α,12β,13β,16α,17β)-10-[(2'α,3'β,4'β,5'β)-3,4-dihydroxy-5,6-dimethyl-2-heptanyl]-5,6-dihydroxy-7a,9a-dimethylhexadecahydro-3H-benzo[c]indeno[5,4-e]oxepin-3-one

(22R,23R,24S)-2α,3β-dihydroxy-22,23-isopropylidenedioxy-B-homo-7-oxa-5α-ergostan-6-one
220398-88-9

(22R,23R,24S)-2α,3β-dihydroxy-22,23-isopropylidenedioxy-B-homo-7-oxa-5α-ergostan-6-one

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: 91 percent / p-TsOH / 8 h / Ambient temperature
2: 86 percent / aq. p-TsOH / dioxane / 4 h / 60 °C
3: Et3N, DMAP / CH2Cl2 / 2 h / Ambient temperature
4: pyridinium dichromate, pyridine / 5 h / 70 °C
5: NaBH4 / tetrahydrofuran / 5 h / Ambient temperature
6: tetra-n-butylammonium fluoride / tetrahydrofuran / 1 h / Ambient temperature
View Scheme
(3α,5α,6α,8β,9α,12β,13β,16α,17β)-10-[(2'α,3'β,4'β,5'β)-3,4-dihydroxy-5,6-dimethyl-2-heptanyl]-5,6-dihydroxy-7a,9a-dimethylhexadecahydro-3H-benzo[c]indeno[5,4-e]oxepin-3-one
72962-43-7

(3α,5α,6α,8β,9α,12β,13β,16α,17β)-10-[(2'α,3'β,4'β,5'β)-3,4-dihydroxy-5,6-dimethyl-2-heptanyl]-5,6-dihydroxy-7a,9a-dimethylhexadecahydro-3H-benzo[c]indeno[5,4-e]oxepin-3-one

(22R,23R,24S)-2β,3α,22,23-tetrahydroxy-B-homo-7-oxa-5α-ergostan-6-one
220401-52-5

(22R,23R,24S)-2β,3α,22,23-tetrahydroxy-B-homo-7-oxa-5α-ergostan-6-one

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: 91 percent / p-TsOH / 8 h / Ambient temperature
2: 86 percent / aq. p-TsOH / dioxane / 4 h / 60 °C
3: 4-dimethylaminopyridine / CH2Cl2 / 2 h / 0 °C
4: triethyl phosphite / 5 h / Heating
5: 50 percent / m-CPBA / CH2Cl2 / 2 h / 0 °C
6: 30 percent / aq. HClO4 / dioxane / 5 h / Ambient temperature
View Scheme
(3α,5α,6α,8β,9α,12β,13β,16α,17β)-10-[(2'α,3'β,4'β,5'β)-3,4-dihydroxy-5,6-dimethyl-2-heptanyl]-5,6-dihydroxy-7a,9a-dimethylhexadecahydro-3H-benzo[c]indeno[5,4-e]oxepin-3-one
72962-43-7

(3α,5α,6α,8β,9α,12β,13β,16α,17β)-10-[(2'α,3'β,4'β,5'β)-3,4-dihydroxy-5,6-dimethyl-2-heptanyl]-5,6-dihydroxy-7a,9a-dimethylhexadecahydro-3H-benzo[c]indeno[5,4-e]oxepin-3-one

(22R,23R,24S)-2α,3β,22,23-tetrahydroxy-B-homo-7-oxa-5α-ergostan-6-one

(22R,23R,24S)-2α,3β,22,23-tetrahydroxy-B-homo-7-oxa-5α-ergostan-6-one

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1: 91 percent / p-TsOH / 8 h / Ambient temperature
2: 86 percent / aq. p-TsOH / dioxane / 4 h / 60 °C
3: Et3N, DMAP / CH2Cl2 / 2 h / Ambient temperature
4: pyridinium dichromate, pyridine / 5 h / 70 °C
5: NaBH4 / tetrahydrofuran / 5 h / Ambient temperature
6: tetra-n-butylammonium fluoride / tetrahydrofuran / 1 h / Ambient temperature
7: 85 percent / 80 percent aq. AcOH / 2 h / 100 °C
View Scheme
(3α,5α,6α,8β,9α,12β,13β,16α,17β)-10-[(2'α,3'β,4'β,5'β)-3,4-dihydroxy-5,6-dimethyl-2-heptanyl]-5,6-dihydroxy-7a,9a-dimethylhexadecahydro-3H-benzo[c]indeno[5,4-e]oxepin-3-one
72962-43-7

(3α,5α,6α,8β,9α,12β,13β,16α,17β)-10-[(2'α,3'β,4'β,5'β)-3,4-dihydroxy-5,6-dimethyl-2-heptanyl]-5,6-dihydroxy-7a,9a-dimethylhexadecahydro-3H-benzo[c]indeno[5,4-e]oxepin-3-one

C32H50O6S

C32H50O6S

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 91 percent / p-TsOH / 8 h / Ambient temperature
2: 86 percent / aq. p-TsOH / dioxane / 4 h / 60 °C
3: 4-dimethylaminopyridine / CH2Cl2 / 2 h / 0 °C
View Scheme
(3α,5α,6α,8β,9α,12β,13β,16α,17β)-10-[(2'α,3'β,4'β,5'β)-3,4-dihydroxy-5,6-dimethyl-2-heptanyl]-5,6-dihydroxy-7a,9a-dimethylhexadecahydro-3H-benzo[c]indeno[5,4-e]oxepin-3-one
72962-43-7

(3α,5α,6α,8β,9α,12β,13β,16α,17β)-10-[(2'α,3'β,4'β,5'β)-3,4-dihydroxy-5,6-dimethyl-2-heptanyl]-5,6-dihydroxy-7a,9a-dimethylhexadecahydro-3H-benzo[c]indeno[5,4-e]oxepin-3-one

(22R,23R,24S)-2α-t-butyldimethylsiloxy-22,23-isopropylidenedioxy-B-homo-7-oxa-5α-ergostan-3,6-dione
220398-87-8

(22R,23R,24S)-2α-t-butyldimethylsiloxy-22,23-isopropylidenedioxy-B-homo-7-oxa-5α-ergostan-3,6-dione

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 91 percent / p-TsOH / 8 h / Ambient temperature
2: 86 percent / aq. p-TsOH / dioxane / 4 h / 60 °C
3: Et3N, DMAP / CH2Cl2 / 2 h / Ambient temperature
4: pyridinium dichromate, pyridine / 5 h / 70 °C
View Scheme

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