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
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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
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inquiryName: 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
Cas:72962-43-7
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inquiryOur 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
Cas:72962-43-7
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inquirybest 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
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inquiryProduct name Plant Growth Regulator Brassinolide(BR) 90% TC, 0.1%SP General info Function: Plant Growth Regulator
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inquiryWe 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
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inquiryOur 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
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inquiryBrassinolide 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
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inquiryHello, 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
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inquiryHebei 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
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inquiryProduct Detail Minimum Order Qty. 10 Gram
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inquiryPRODUCT DETAILS
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inquiryHenan 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
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inquiry1.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
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inquiryA 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
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inquiryHigh 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
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inquiryProduct 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
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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
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inquiry1.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
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inquiry2α,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
Conditions | Yield |
---|---|
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
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
B
(22R,23R,24S)-2α,3α,22,23-tetrahydroxy-6-oxa-7a-homo-5α-campestan-7-one
Conditions | Yield |
---|---|
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
(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 | Yield |
---|---|
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
(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 | Yield |
---|---|
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
(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 | Yield |
---|---|
Yield given. Multistep reaction; | |
Multi-step reaction with 2 steps 1: pyridine, N,N-dimethylaminopyridine View Scheme |
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
Conditions | Yield |
---|---|
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
(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 | Yield |
---|---|
With sodium hydroxide In methanol for 3h; Heating; | 1.79 g |
(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 | Yield |
---|---|
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
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
B
(22R,23R,24S)-2α,3α,22,23-tetrahydroxy-6-oxa-7a-homo-5α-campestan-7-one
Conditions | Yield |
---|---|
Yield given. Multistep reaction. Yields of byproduct given; |
(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
Conditions | Yield |
---|---|
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
(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 | Yield |
---|---|
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
(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 | Yield |
---|---|
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
(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 | Yield |
---|---|
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
(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 | Yield |
---|---|
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
(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 | Yield |
---|---|
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
(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 | Yield |
---|---|
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
(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 | Yield |
---|---|
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
(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 | Yield |
---|---|
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
(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 | Yield |
---|---|
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
(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 | Yield |
---|---|
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
(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 | Yield |
---|---|
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
(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 | Yield |
---|---|
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 |
(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 | Yield |
---|---|
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 |
(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 | Yield |
---|---|
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
(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 | Yield |
---|---|
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
(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 | Yield |
---|---|
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
(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 | Yield |
---|---|
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
(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 | Yield |
---|---|
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
(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 | Yield |
---|---|
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
(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 | Yield |
---|---|
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
acetic anhydride
2α,3α-22R,23R-tetraacetoxy-B-homo-7-oxa-24S-methyl-5α-cholestan-6-one
Conditions | Yield |
---|---|
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
acetone
C34H56O6
Conditions | Yield |
---|---|
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
2,2-dimethoxy-propane
Conditions | Yield |
---|---|
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
Conditions | Yield |
---|---|
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
2,3,22,33-tetra-O-acetyl-25-hydroxybrassinolide
Conditions | Yield |
---|---|
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
Conditions | Yield |
---|---|
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
Conditions | Yield |
---|---|
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
Conditions | Yield |
---|---|
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
Conditions | Yield |
---|---|
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
Conditions | Yield |
---|---|
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
Conditions | Yield |
---|---|
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
Conditions | Yield |
---|---|
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
2,3,22,33-tetra-O-acetyl-14α,25-dihydroxybrassinolide
Conditions | Yield |
---|---|
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
(22R,23R,24S)-22,23-isopropylidenedioxy-B-homo-7-oxa-5α-ergost-2-en-6-one
Conditions | Yield |
---|---|
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
(22R,23R,24S)-2α,3α-epoxy-22,23-isopropylidenedioxy-B-homo-7-oxa-5α-ergostan-6-one
Conditions | Yield |
---|---|
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
(22R,23R,24S)-2α,3α-dihydroxy-22,23-isopropylidenedioxy-B-homo-7-oxa-5α-ergostan-6-one
Conditions | Yield |
---|---|
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
(22R,23R,24S)-2α,3β-dihydroxy-22,23-isopropylidenedioxy-B-homo-7-oxa-5α-ergostan-6-one
Conditions | Yield |
---|---|
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
(22R,23R,24S)-2β,3α,22,23-tetrahydroxy-B-homo-7-oxa-5α-ergostan-6-one
Conditions | Yield |
---|---|
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
Conditions | Yield |
---|---|
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
Conditions | Yield |
---|---|
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
(22R,23R,24S)-2α-t-butyldimethylsiloxy-22,23-isopropylidenedioxy-B-homo-7-oxa-5α-ergostan-3,6-dione
Conditions | Yield |
---|---|
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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