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
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inquiryOur Advantage Rich Experience Our products are sold all over Europe,North&South America, Sino-East, Asia and pacific area as well as Africa,we establish long term. Quality service Company cooperates with research institutes. We strictly con
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inquiry1.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
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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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inquiryZibo 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
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inquiryZhenyu biotech exported this product to many countries and regions at best price. if you are looking for the material's manufacturer or supplier in china, zhenyu biotech is your best choice. pls contact with us freely for getting detailed
Cas:1944-63-4
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inquiryTAIHO Unique Advantages:1.We're factory2.Free samples available3.Commodity inspection can be done4.ISO9001,Kosher certifications5.10 years experiences Storage:Store in cool &dry place Package:aluminium foil bag/fiber can/plastic drum Application:comp
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inquiryhigh purity lowest priceAppearance:solid or liquid Storage:in sealed air resistant place Package:Foil bag; Drum; Plastic bottle Application:Pharma;Industry;Agricultural Transportation:by sea or air Port:Beijing or Guangzhou
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inquiryfactory?direct?sale Application:healing drugs
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inquiry3-[(3AS,4S,7AS)-7A-METHYL-1,5-DIOXOOCTAHYDRO-1H-INDEN-4-YL]PROPANOIC ACIDAppearance:white crystalline powder Storage:Store in dry, dark and ventilated place Package:25KG drum Application:intermediate Transportation:by air, by sea, by express
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inquiryfactory?direct?saleAppearance:White powder Storage:Sealed and preserved Package:200/Kilograms Application:healing drugs Transportation:By sea Port:Shanghai/tianjin
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inquiryZhengzhou Kingorgchem Chemical Technology Co., Ltd. was founded on the basis of Organophosphorus Chemistry Lab of Institute of Chemistry Henan Academy of Sciences in 2015. The laboratory covers 600 m2 and the pilot plant covers 2000 m2. Kingorgchem i
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inquiryBetterbiochem is specialized in APIs, pharmaceutical intermediates & fine chemicals. 1. The best quality, competitive price. 2. The best service before or after shipment. 3. Rich experience in export operation. 4. Rich experience in
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inquiryShanghai, Run-Biotech Co., Ltd is a leading domestic pharmaceutical, biopharmaceutical, and health care products R & D outsourcing services company. As an innovation-driven and customer-focused company, Run Biotech provides a broad and integrated por
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inquiry3aα-H-4α-(3’-propionic acid)-7aβ-methylhexahydro-1,5-indanedione
Conditions | Yield |
---|---|
With sodium chlorite; sodium dihydrogenphosphate dihydrate; 2-methyl-but-2-ene In water; tert-butyl alcohol at 20℃; for 18h; | 40% |
[3-(2-methyl-[1,3]dioxolan-2-yl)-propyl]-magnesium chloride
C18H26O5
A
3aα-H-4α-(3’-propionic acid)-7aβ-methylhexahydro-1,5-indanedione
B
2,2-dimethyl-6-(2-methyl-[1,3]dioxolan-2-yl)-hexan-3-one
C
(+)-3,3-ethylenedioxy-4,5-seco-19-norandrost-9-en-5,17-dione
Conditions | Yield |
---|---|
In tetrahydrofuran at -70℃; for 1h; Yield given; |
(1R,3aS,4S,7aS)-4-(2-Carboxy-ethyl)-1-hydroxy-7a-methyl-5-oxo-octahydro-indene-1-carboxylic acid
3aα-H-4α-(3’-propionic acid)-7aβ-methylhexahydro-1,5-indanedione
Conditions | Yield |
---|---|
With sodium bismuthate In acetic acid |
(S)-Halos-Parish ketone
3aα-H-4α-(3’-propionic acid)-7aβ-methylhexahydro-1,5-indanedione
Conditions | Yield |
---|---|
Multi-step reaction with 8 steps 1.1: sodium tetrahydroborate / ethanol / 0 °C / Inert atmosphere 2.1: 1-methyl-1H-imidazole; iodine / tetrahydrofuran / 42 h / 20 °C / Inert atmosphere 3.1: dimethyl sulfoxide; sodium hydride / tetrahydrofuran; mineral oil / 2 h / 0 - 20 °C / Inert atmosphere 3.2: 18 h / 20 °C / Inert atmosphere 4.1: palladium on activated charcoal; hydrogen 5.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 18 h / 20 °C 6.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 18 h / 20 °C 7.1: periodic acid / ethyl acetate / 20 °C 8.1: sodium chlorite; sodium dihydrogenphosphate dihydrate; 2-methyl-but-2-ene / water; tert-butyl alcohol / 18 h / 20 °C View Scheme | |
Multi-step reaction with 8 steps 1.1: sodium tetrahydroborate / ethanol / 0 °C / Inert atmosphere 2.1: 1-methyl-1H-imidazole; iodine / tetrahydrofuran / 42 h / 20 °C / Inert atmosphere 3.1: dimethyl sulfoxide; sodium hydride / tetrahydrofuran; mineral oil / 2 h / 0 - 20 °C / Inert atmosphere 3.2: 18 h / 20 °C / Inert atmosphere 4.1: nickel(II) chloride hexahydrate; sodium tetrahydroborate / methanol / 1 h / -35 °C 5.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 18 h / 20 °C 6.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 18 h / 20 °C 7.1: periodic acid / ethyl acetate / 20 °C 8.1: sodium chlorite; sodium dihydrogenphosphate dihydrate; 2-methyl-but-2-ene / water; tert-butyl alcohol / 18 h / 20 °C View Scheme | |
Multi-step reaction with 8 steps 1.1: sodium tetrahydroborate / ethanol / 0 °C / Inert atmosphere 2.1: 2,6-dimethylpyridine / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere 3.1: dimethyl sulfoxide; sodium hydride / tetrahydrofuran; mineral oil / 2 h / 0 - 20 °C / Inert atmosphere 3.2: 18 h / 20 °C / Inert atmosphere 4.1: palladium on activated charcoal; hydrogen 5.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 18 h / 20 °C 6.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 18 h / 20 °C 7.1: periodic acid / ethyl acetate / 20 °C 8.1: sodium chlorite; sodium dihydrogenphosphate dihydrate; 2-methyl-but-2-ene / water; tert-butyl alcohol / 18 h / 20 °C View Scheme | |
Multi-step reaction with 8 steps 1.1: sodium tetrahydroborate / ethanol / 0 °C / Inert atmosphere 2.1: 2,6-dimethylpyridine / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere 3.1: dimethyl sulfoxide; sodium hydride / tetrahydrofuran; mineral oil / 2 h / 0 - 20 °C / Inert atmosphere 3.2: 18 h / 20 °C / Inert atmosphere 4.1: nickel(II) chloride hexahydrate; sodium tetrahydroborate / methanol / 1 h / -35 °C 5.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 18 h / 20 °C 6.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 18 h / 20 °C 7.1: periodic acid / ethyl acetate / 20 °C 8.1: sodium chlorite; sodium dihydrogenphosphate dihydrate; 2-methyl-but-2-ene / water; tert-butyl alcohol / 18 h / 20 °C View Scheme |
3aα-H-4α-(3’-propionic acid)-7aβ-methylhexahydro-1,5-indanedione
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: nickel(II) chloride hexahydrate; sodium tetrahydroborate / methanol / 1 h / -35 °C 2: tetrabutyl ammonium fluoride / tetrahydrofuran / 18 h / 20 °C 3: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 18 h / 20 °C 4: periodic acid / ethyl acetate / 20 °C 5: sodium chlorite; sodium dihydrogenphosphate dihydrate; 2-methyl-but-2-ene / water; tert-butyl alcohol / 18 h / 20 °C View Scheme | |
Multi-step reaction with 5 steps 1: palladium on activated charcoal; hydrogen 2: tetrabutyl ammonium fluoride / tetrahydrofuran / 18 h / 20 °C 3: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 18 h / 20 °C 4: periodic acid / ethyl acetate / 20 °C 5: sodium chlorite; sodium dihydrogenphosphate dihydrate; 2-methyl-but-2-ene / water; tert-butyl alcohol / 18 h / 20 °C View Scheme |
3aα-H-4α-(3’-propionic acid)-7aβ-methylhexahydro-1,5-indanedione
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: tetrabutyl ammonium fluoride / tetrahydrofuran / 18 h / 20 °C 2: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 18 h / 20 °C 3: periodic acid / ethyl acetate / 20 °C 4: sodium chlorite; sodium dihydrogenphosphate dihydrate; 2-methyl-but-2-ene / water; tert-butyl alcohol / 18 h / 20 °C View Scheme |
3aα-H-4α-(3’-propionic acid)-7aβ-methylhexahydro-1,5-indanedione
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 18 h / 20 °C 2: periodic acid / ethyl acetate / 20 °C 3: sodium chlorite; sodium dihydrogenphosphate dihydrate; 2-methyl-but-2-ene / water; tert-butyl alcohol / 18 h / 20 °C View Scheme |
(1S,7aS)-1-hydroxy-7a-methyl-2,3,7,7a-tetrahydro-1H-inden-5(6H)-one
3aα-H-4α-(3’-propionic acid)-7aβ-methylhexahydro-1,5-indanedione
Conditions | Yield |
---|---|
Multi-step reaction with 7 steps 1.1: 2,6-dimethylpyridine / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere 2.1: dimethyl sulfoxide; sodium hydride / tetrahydrofuran; mineral oil / 2 h / 0 - 20 °C / Inert atmosphere 2.2: 18 h / 20 °C / Inert atmosphere 3.1: palladium on activated charcoal; hydrogen 4.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 18 h / 20 °C 5.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 18 h / 20 °C 6.1: periodic acid / ethyl acetate / 20 °C 7.1: sodium chlorite; sodium dihydrogenphosphate dihydrate; 2-methyl-but-2-ene / water; tert-butyl alcohol / 18 h / 20 °C View Scheme | |
Multi-step reaction with 7 steps 1.1: 2,6-dimethylpyridine / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere 2.1: dimethyl sulfoxide; sodium hydride / tetrahydrofuran; mineral oil / 2 h / 0 - 20 °C / Inert atmosphere 2.2: 18 h / 20 °C / Inert atmosphere 3.1: nickel(II) chloride hexahydrate; sodium tetrahydroborate / methanol / 1 h / -35 °C 4.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 18 h / 20 °C 5.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 18 h / 20 °C 6.1: periodic acid / ethyl acetate / 20 °C 7.1: sodium chlorite; sodium dihydrogenphosphate dihydrate; 2-methyl-but-2-ene / water; tert-butyl alcohol / 18 h / 20 °C View Scheme | |
Multi-step reaction with 7 steps 1.1: 1-methyl-1H-imidazole; iodine / tetrahydrofuran / 42 h / 20 °C / Inert atmosphere 2.1: dimethyl sulfoxide; sodium hydride / tetrahydrofuran; mineral oil / 2 h / 0 - 20 °C / Inert atmosphere 2.2: 18 h / 20 °C / Inert atmosphere 3.1: palladium on activated charcoal; hydrogen 4.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 18 h / 20 °C 5.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 18 h / 20 °C 6.1: periodic acid / ethyl acetate / 20 °C 7.1: sodium chlorite; sodium dihydrogenphosphate dihydrate; 2-methyl-but-2-ene / water; tert-butyl alcohol / 18 h / 20 °C View Scheme | |
Multi-step reaction with 7 steps 1.1: 1-methyl-1H-imidazole; iodine / tetrahydrofuran / 42 h / 20 °C / Inert atmosphere 2.1: dimethyl sulfoxide; sodium hydride / tetrahydrofuran; mineral oil / 2 h / 0 - 20 °C / Inert atmosphere 2.2: 18 h / 20 °C / Inert atmosphere 3.1: nickel(II) chloride hexahydrate; sodium tetrahydroborate / methanol / 1 h / -35 °C 4.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 18 h / 20 °C 5.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 18 h / 20 °C 6.1: periodic acid / ethyl acetate / 20 °C 7.1: sodium chlorite; sodium dihydrogenphosphate dihydrate; 2-methyl-but-2-ene / water; tert-butyl alcohol / 18 h / 20 °C View Scheme |
3aα-H-4α-(3’-propionic acid)-7aβ-methylhexahydro-1,5-indanedione
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: periodic acid / ethyl acetate / 20 °C 2: sodium chlorite; sodium dihydrogenphosphate dihydrate; 2-methyl-but-2-ene / water; tert-butyl alcohol / 18 h / 20 °C View Scheme |
(1S,7aS)-1-((tert-butyldimethylsilyl)oxy)-7a-methyl-1,2,3,6,7,7a-hexahydro-5H-inden-5-one
3aα-H-4α-(3’-propionic acid)-7aβ-methylhexahydro-1,5-indanedione
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1.1: dimethyl sulfoxide; sodium hydride / tetrahydrofuran; mineral oil / 2 h / 0 - 20 °C / Inert atmosphere 1.2: 18 h / 20 °C / Inert atmosphere 2.1: nickel(II) chloride hexahydrate; sodium tetrahydroborate / methanol / 1 h / -35 °C 3.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 18 h / 20 °C 4.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 18 h / 20 °C 5.1: periodic acid / ethyl acetate / 20 °C 6.1: sodium chlorite; sodium dihydrogenphosphate dihydrate; 2-methyl-but-2-ene / water; tert-butyl alcohol / 18 h / 20 °C View Scheme | |
Multi-step reaction with 6 steps 1.1: dimethyl sulfoxide; sodium hydride / tetrahydrofuran; mineral oil / 2 h / 0 - 20 °C / Inert atmosphere 1.2: 18 h / 20 °C / Inert atmosphere 2.1: palladium on activated charcoal; hydrogen 3.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 18 h / 20 °C 4.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 18 h / 20 °C 5.1: periodic acid / ethyl acetate / 20 °C 6.1: sodium chlorite; sodium dihydrogenphosphate dihydrate; 2-methyl-but-2-ene / water; tert-butyl alcohol / 18 h / 20 °C View Scheme |
methanol
3aα-H-4α-(3’-propionic acid)-7aβ-methylhexahydro-1,5-indanedione
(3aS,7aS)-1,5-dioxo-4α-methylpropionic-3aα,4,5,6,7,7a-hexahydro-7a-methylindan
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid for 23h; | 96% |
With toluene-4-sulfonic acid for 2h; Esterification; Heating; | 90% |
3aα-H-4α-(3’-propionic acid)-7aβ-methylhexahydro-1,5-indanedione
1,6,6a,7,8,9,9a,9b-octahydro-6a-methyl-<6aS-(6aα,9aβ,9bα)>cyclopenta<1>benzopyran-3(2H)-7-dione
Conditions | Yield |
---|---|
With sodium acetate; acetic anhydride for 4h; Heating; | 93% |
With perchloric acid; acetic anhydride In ethyl acetate | 81% |
With perchloric acid; acetic anhydride In ethyl acetate | 80% |
3aα-H-4α-(3’-propionic acid)-7aβ-methylhexahydro-1,5-indanedione
A
(3aS,9aS,9bS)-3a-Methyl-1,2,4,6,8,9,9a,9b-octahydro-3aH-6-aza-cyclopenta[a]naphthalene-3,7-dione
Conditions | Yield |
---|---|
With formic acid; ammonium bicarbonate at 120℃; for 1h; Yields of byproduct given; | A 59% B n/a |
With formic acid; ammonium bicarbonate at 120℃; for 1h; Yield given. Yields of byproduct given; |
3aα-H-4α-(3’-propionic acid)-7aβ-methylhexahydro-1,5-indanedione
Conditions | Yield |
---|---|
With pyridine; copper diacetate; [bis(acetoxy)iodo]benzene In benzene for 8h; Decarboxylation; Heating; | 40% |
3aα-H-4α-(3’-propionic acid)-7aβ-methylhexahydro-1,5-indanedione
pivaloyl chloride
C18H26O5
Conditions | Yield |
---|---|
With triethylamine In tetrahydrofuran at -20℃; Yield given; | |
With triethylamine In tetrahydrofuran at -30℃; for 3.5h; Temperature; Inert atmosphere; |
3aα-H-4α-(3’-propionic acid)-7aβ-methylhexahydro-1,5-indanedione
17β-Hydroxy-5-oxo-des-A-10-aza-oestran
Conditions | Yield |
---|---|
With hydrogenchloride; formic acid; sodium cyanoborohydride; ammonium bicarbonate 1.) 120 deg C, 1 h, 2.) MeOH, pH 1.5-2, room temperature, 48 h; Yield given. Multistep reaction; |
Conditions | Yield |
---|---|
Multi-step reaction with 12 steps 1.1: 90 percent / p-TsOH / 2 h / Heating 2.1: 86 percent / L-Selectride / tetrahydrofuran / 0.5 h / -78 °C 3.1: 82 percent / Pb(OAc)4; Cu(OAc)2; pyridine / benzene / Heating 4.1: 85 percent / K2CO3 / methanol / 20 °C 5.1: 78 percent / 4-DMAP / 3 h / 20 °C 6.1: 78 percent / t-BuOK / dimethylsulfoxide; tetrahydrofuran / 1 h / 0 °C 7.1: KBH4 / methanol / 1 h / 0 °C 8.1: 80 percent / imidazole / dimethylformamide / 18 h / 20 °C 9.1: 70 percent / 1,2-dichloro-ethane / UV-irradiation 10.1: t-BuOK / tetrahydrofuran / 0.25 h / -105 °C 10.2: NCS / tetrahydrofuran / -105 - 25 °C 10.3: 60 percent / t-BuOK / tetrahydrofuran / 4 h / 20 °C 11.1: KNH(CH2)3NH2 / tetrahydrofuran / 15 h / 20 °C 11.2: 48 percent HF / acetonitrile / 20 °C 11.3: 45 percent / TFA; Et3SiH / benzene / 15 h / 20 °C 12.1: 80 percent / TFA; Pb(OTFA)4 / 0.5 h / 20 °C View Scheme | |
Multi-step reaction with 12 steps 1.1: 90 percent / p-TsOH / 2 h / Heating 2.1: 86 percent / L-Selectride / tetrahydrofuran / 0.5 h / -78 °C 3.1: 82 percent / Pb(OAc)4; Cu(OAc)2; pyridine / benzene / Heating 4.1: 85 percent / K2CO3 / methanol / 20 °C 5.1: 65 percent / Et3N / CH2Cl2 / 2 h / 0 °C 6.1: t-BuOK / tetrahydrofuran / 0 °C 7.1: KBH4 / methanol / 1 h / 0 °C 8.1: 80 percent / imidazole / dimethylformamide / 18 h / 20 °C 9.1: 70 percent / 1,2-dichloro-ethane / UV-irradiation 10.1: t-BuOK / tetrahydrofuran / 0.25 h / -105 °C 10.2: NCS / tetrahydrofuran / -105 - 25 °C 10.3: 60 percent / t-BuOK / tetrahydrofuran / 4 h / 20 °C 11.1: KNH(CH2)3NH2 / tetrahydrofuran / 15 h / 20 °C 11.2: 48 percent HF / acetonitrile / 20 °C 11.3: 45 percent / TFA; Et3SiH / benzene / 15 h / 20 °C 12.1: 80 percent / TFA; Pb(OTFA)4 / 0.5 h / 20 °C View Scheme | |
Multi-step reaction with 13 steps 1.1: 90 percent / p-TsOH / 2 h / Heating 2.1: 86 percent / L-Selectride / tetrahydrofuran / 0.5 h / -78 °C 3.1: 78 percent / iodobenzene diacetate; I2 / cyclohexane / Photolysis 4.1: 30 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / benzene / Heating 5.1: 85 percent / K2CO3 / methanol / 20 °C 6.1: 78 percent / 4-DMAP / 3 h / 20 °C 7.1: 78 percent / t-BuOK / dimethylsulfoxide; tetrahydrofuran / 1 h / 0 °C 8.1: KBH4 / methanol / 1 h / 0 °C 9.1: 80 percent / imidazole / dimethylformamide / 18 h / 20 °C 10.1: 70 percent / 1,2-dichloro-ethane / UV-irradiation 11.1: t-BuOK / tetrahydrofuran / 0.25 h / -105 °C 11.2: NCS / tetrahydrofuran / -105 - 25 °C 11.3: 60 percent / t-BuOK / tetrahydrofuran / 4 h / 20 °C 12.1: KNH(CH2)3NH2 / tetrahydrofuran / 15 h / 20 °C 12.2: 48 percent HF / acetonitrile / 20 °C 12.3: 45 percent / TFA; Et3SiH / benzene / 15 h / 20 °C 13.1: 80 percent / TFA; Pb(OTFA)4 / 0.5 h / 20 °C View Scheme | |
Multi-step reaction with 13 steps 1.1: 90 percent / p-TsOH / 2 h / Heating 2.1: 86 percent / L-Selectride / tetrahydrofuran / 0.5 h / -78 °C 3.1: 78 percent / iodobenzene diacetate; I2 / cyclohexane / Photolysis 4.1: 30 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / benzene / Heating 5.1: 85 percent / K2CO3 / methanol / 20 °C 6.1: 65 percent / Et3N / CH2Cl2 / 2 h / 0 °C 7.1: t-BuOK / tetrahydrofuran / 0 °C 8.1: KBH4 / methanol / 1 h / 0 °C 9.1: 80 percent / imidazole / dimethylformamide / 18 h / 20 °C 10.1: 70 percent / 1,2-dichloro-ethane / UV-irradiation 11.1: t-BuOK / tetrahydrofuran / 0.25 h / -105 °C 11.2: NCS / tetrahydrofuran / -105 - 25 °C 11.3: 60 percent / t-BuOK / tetrahydrofuran / 4 h / 20 °C 12.1: KNH(CH2)3NH2 / tetrahydrofuran / 15 h / 20 °C 12.2: 48 percent HF / acetonitrile / 20 °C 12.3: 45 percent / TFA; Et3SiH / benzene / 15 h / 20 °C 13.1: 80 percent / TFA; Pb(OTFA)4 / 0.5 h / 20 °C View Scheme |
3aα-H-4α-(3’-propionic acid)-7aβ-methylhexahydro-1,5-indanedione
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1: 90 percent / p-TsOH / 2 h / Heating 2: 86 percent / L-Selectride / tetrahydrofuran / 0.5 h / -78 °C 3: 82 percent / Pb(OAc)4; Cu(OAc)2; pyridine / benzene / Heating 4: 85 percent / K2CO3 / methanol / 20 °C 5: 78 percent / 4-DMAP / 3 h / 20 °C 6: 65 percent / t-BuOK / tetrahydrofuran / 0 °C View Scheme | |
Multi-step reaction with 6 steps 1: 90 percent / p-TsOH / 2 h / Heating 2: 86 percent / L-Selectride / tetrahydrofuran / 0.5 h / -78 °C 3: 82 percent / Pb(OAc)4; Cu(OAc)2; pyridine / benzene / Heating 4: 85 percent / K2CO3 / methanol / 20 °C 5: 65 percent / Et3N / CH2Cl2 / 2 h / 0 °C 6: t-BuOK / tetrahydrofuran / 0 °C View Scheme | |
Multi-step reaction with 7 steps 1: 90 percent / p-TsOH / 2 h / Heating 2: 86 percent / L-Selectride / tetrahydrofuran / 0.5 h / -78 °C 3: 78 percent / iodobenzene diacetate; I2 / cyclohexane / Photolysis 4: 30 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / benzene / Heating 5: 85 percent / K2CO3 / methanol / 20 °C 6: 78 percent / 4-DMAP / 3 h / 20 °C 7: 65 percent / t-BuOK / tetrahydrofuran / 0 °C View Scheme | |
Multi-step reaction with 7 steps 1: 90 percent / p-TsOH / 2 h / Heating 2: 86 percent / L-Selectride / tetrahydrofuran / 0.5 h / -78 °C 3: 78 percent / iodobenzene diacetate; I2 / cyclohexane / Photolysis 4: 30 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / benzene / Heating 5: 85 percent / K2CO3 / methanol / 20 °C 6: 65 percent / Et3N / CH2Cl2 / 2 h / 0 °C 7: t-BuOK / tetrahydrofuran / 0 °C View Scheme |
3aα-H-4α-(3’-propionic acid)-7aβ-methylhexahydro-1,5-indanedione
(3aS,7aS)-7a-Methyl-4-vinyl-2,3,3a,6,7,7a-hexahydro-inden-1-one
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1: 90 percent / p-TsOH / 2 h / Heating 2: 86 percent / L-Selectride / tetrahydrofuran / 0.5 h / -78 °C 3: 82 percent / Pb(OAc)4; Cu(OAc)2; pyridine / benzene / Heating 4: 85 percent / K2CO3 / methanol / 20 °C 5: 78 percent / 4-DMAP / 3 h / 20 °C 6: 78 percent / t-BuOK / dimethylsulfoxide; tetrahydrofuran / 1 h / 0 °C View Scheme | |
Multi-step reaction with 6 steps 1: 90 percent / p-TsOH / 2 h / Heating 2: 86 percent / L-Selectride / tetrahydrofuran / 0.5 h / -78 °C 3: 82 percent / Pb(OAc)4; Cu(OAc)2; pyridine / benzene / Heating 4: 85 percent / K2CO3 / methanol / 20 °C 5: 65 percent / Et3N / CH2Cl2 / 2 h / 0 °C 6: t-BuOK / tetrahydrofuran / 0 °C View Scheme | |
Multi-step reaction with 7 steps 1: 90 percent / p-TsOH / 2 h / Heating 2: 86 percent / L-Selectride / tetrahydrofuran / 0.5 h / -78 °C 3: 78 percent / iodobenzene diacetate; I2 / cyclohexane / Photolysis 4: 30 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / benzene / Heating 5: 85 percent / K2CO3 / methanol / 20 °C 6: 78 percent / 4-DMAP / 3 h / 20 °C 7: 78 percent / t-BuOK / dimethylsulfoxide; tetrahydrofuran / 1 h / 0 °C View Scheme | |
Multi-step reaction with 7 steps 1: 90 percent / p-TsOH / 2 h / Heating 2: 86 percent / L-Selectride / tetrahydrofuran / 0.5 h / -78 °C 3: 78 percent / iodobenzene diacetate; I2 / cyclohexane / Photolysis 4: 30 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / benzene / Heating 5: 85 percent / K2CO3 / methanol / 20 °C 6: 65 percent / Et3N / CH2Cl2 / 2 h / 0 °C 7: t-BuOK / tetrahydrofuran / 0 °C View Scheme |
3aα-H-4α-(3’-propionic acid)-7aβ-methylhexahydro-1,5-indanedione
(1S,3aS,7aS)-7a-Methyl-4-vinyl-2,3,3a,6,7,7a-hexahydro-1H-inden-1-ol
Conditions | Yield |
---|---|
Multi-step reaction with 7 steps 1: 90 percent / p-TsOH / 2 h / Heating 2: 86 percent / L-Selectride / tetrahydrofuran / 0.5 h / -78 °C 3: 82 percent / Pb(OAc)4; Cu(OAc)2; pyridine / benzene / Heating 4: 85 percent / K2CO3 / methanol / 20 °C 5: 78 percent / 4-DMAP / 3 h / 20 °C 6: 78 percent / t-BuOK / dimethylsulfoxide; tetrahydrofuran / 1 h / 0 °C 7: KBH4 / methanol / 1 h / 0 °C View Scheme | |
Multi-step reaction with 7 steps 1: 90 percent / p-TsOH / 2 h / Heating 2: 86 percent / L-Selectride / tetrahydrofuran / 0.5 h / -78 °C 3: 82 percent / Pb(OAc)4; Cu(OAc)2; pyridine / benzene / Heating 4: 85 percent / K2CO3 / methanol / 20 °C 5: 65 percent / Et3N / CH2Cl2 / 2 h / 0 °C 6: t-BuOK / tetrahydrofuran / 0 °C 7: KBH4 / methanol / 1 h / 0 °C View Scheme | |
Multi-step reaction with 8 steps 1: 90 percent / p-TsOH / 2 h / Heating 2: 86 percent / L-Selectride / tetrahydrofuran / 0.5 h / -78 °C 3: 78 percent / iodobenzene diacetate; I2 / cyclohexane / Photolysis 4: 30 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / benzene / Heating 5: 85 percent / K2CO3 / methanol / 20 °C 6: 78 percent / 4-DMAP / 3 h / 20 °C 7: 78 percent / t-BuOK / dimethylsulfoxide; tetrahydrofuran / 1 h / 0 °C 8: KBH4 / methanol / 1 h / 0 °C View Scheme | |
Multi-step reaction with 8 steps 1: 90 percent / p-TsOH / 2 h / Heating 2: 86 percent / L-Selectride / tetrahydrofuran / 0.5 h / -78 °C 3: 78 percent / iodobenzene diacetate; I2 / cyclohexane / Photolysis 4: 30 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / benzene / Heating 5: 85 percent / K2CO3 / methanol / 20 °C 6: 65 percent / Et3N / CH2Cl2 / 2 h / 0 °C 7: t-BuOK / tetrahydrofuran / 0 °C 8: KBH4 / methanol / 1 h / 0 °C View Scheme |
3aα-H-4α-(3’-propionic acid)-7aβ-methylhexahydro-1,5-indanedione
(3aS,7aS)-4α-ethenyl-5α-hydroxy-1-oxo-,4,5,6,7,7a-hexahydro-7a-methylindan
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: 90 percent / p-TsOH / 2 h / Heating 2: 86 percent / L-Selectride / tetrahydrofuran / 0.5 h / -78 °C 3: 82 percent / Pb(OAc)4; Cu(OAc)2; pyridine / benzene / Heating 4: 85 percent / K2CO3 / methanol / 20 °C View Scheme | |
Multi-step reaction with 5 steps 1: 90 percent / p-TsOH / 2 h / Heating 2: 86 percent / L-Selectride / tetrahydrofuran / 0.5 h / -78 °C 3: 78 percent / iodobenzene diacetate; I2 / cyclohexane / Photolysis 4: 30 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / benzene / Heating 5: 85 percent / K2CO3 / methanol / 20 °C View Scheme |
3aα-H-4α-(3’-propionic acid)-7aβ-methylhexahydro-1,5-indanedione
(3aS,7aS)-4α-ethenyl-5α-formyloxy-1-oxo-,4,5,6,7,7a-hexahydro-7a-methylindan
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 90 percent / p-TsOH / 2 h / Heating 2: 86 percent / L-Selectride / tetrahydrofuran / 0.5 h / -78 °C 3: 82 percent / Pb(OAc)4; Cu(OAc)2; pyridine / benzene / Heating View Scheme | |
Multi-step reaction with 4 steps 1: 90 percent / p-TsOH / 2 h / Heating 2: 86 percent / L-Selectride / tetrahydrofuran / 0.5 h / -78 °C 3: 78 percent / iodobenzene diacetate; I2 / cyclohexane / Photolysis 4: 30 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / benzene / Heating View Scheme |
3aα-H-4α-(3’-propionic acid)-7aβ-methylhexahydro-1,5-indanedione
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 90 percent / p-TsOH / 2 h / Heating 2: 86 percent / L-Selectride / tetrahydrofuran / 0.5 h / -78 °C View Scheme |
3aα-H-4α-(3’-propionic acid)-7aβ-methylhexahydro-1,5-indanedione
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 90 percent / p-TsOH / 2 h / Heating 2: 85 percent / KBH4 / methanol / 0.5 h / 0 °C View Scheme |
3aα-H-4α-(3’-propionic acid)-7aβ-methylhexahydro-1,5-indanedione
(3aS,7aS)-4α-ethenyl-5α-methanesulfonyl-1-oxo-,4,5,6,7,7a-hexahydro-7a-methylindan
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: 90 percent / p-TsOH / 2 h / Heating 2: 86 percent / L-Selectride / tetrahydrofuran / 0.5 h / -78 °C 3: 82 percent / Pb(OAc)4; Cu(OAc)2; pyridine / benzene / Heating 4: 85 percent / K2CO3 / methanol / 20 °C 5: 65 percent / Et3N / CH2Cl2 / 2 h / 0 °C View Scheme | |
Multi-step reaction with 6 steps 1: 90 percent / p-TsOH / 2 h / Heating 2: 86 percent / L-Selectride / tetrahydrofuran / 0.5 h / -78 °C 3: 78 percent / iodobenzene diacetate; I2 / cyclohexane / Photolysis 4: 30 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / benzene / Heating 5: 85 percent / K2CO3 / methanol / 20 °C 6: 65 percent / Et3N / CH2Cl2 / 2 h / 0 °C View Scheme |
3aα-H-4α-(3’-propionic acid)-7aβ-methylhexahydro-1,5-indanedione
(3aS,7aS)-5-formyloxy-4α-(2'-iodoethyl)-1-oxo-3a,4,5,6,7,7a-hexahydro-7a-methylindan
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 90 percent / p-TsOH / 2 h / Heating 2: 86 percent / L-Selectride / tetrahydrofuran / 0.5 h / -78 °C 3: 78 percent / iodobenzene diacetate; I2 / cyclohexane / Photolysis View Scheme |
3aα-H-4α-(3’-propionic acid)-7aβ-methylhexahydro-1,5-indanedione
A
(3aS,7aS)-4α-ethenyl-1-[(tert-butyldimethylsilyl)oxy]-3a-methyl-3a,6,7,7a-tetrahydro-4-indene
Conditions | Yield |
---|---|
Multi-step reaction with 8 steps 1: 90 percent / p-TsOH / 2 h / Heating 2: 86 percent / L-Selectride / tetrahydrofuran / 0.5 h / -78 °C 3: 82 percent / Pb(OAc)4; Cu(OAc)2; pyridine / benzene / Heating 4: 85 percent / K2CO3 / methanol / 20 °C 5: 78 percent / 4-DMAP / 3 h / 20 °C 6: 78 percent / t-BuOK / dimethylsulfoxide; tetrahydrofuran / 1 h / 0 °C 7: KBH4 / methanol / 1 h / 0 °C 8: 80 percent / imidazole / dimethylformamide / 18 h / 20 °C View Scheme | |
Multi-step reaction with 8 steps 1: 90 percent / p-TsOH / 2 h / Heating 2: 86 percent / L-Selectride / tetrahydrofuran / 0.5 h / -78 °C 3: 82 percent / Pb(OAc)4; Cu(OAc)2; pyridine / benzene / Heating 4: 85 percent / K2CO3 / methanol / 20 °C 5: 65 percent / Et3N / CH2Cl2 / 2 h / 0 °C 6: t-BuOK / tetrahydrofuran / 0 °C 7: KBH4 / methanol / 1 h / 0 °C 8: 80 percent / imidazole / dimethylformamide / 18 h / 20 °C View Scheme | |
Multi-step reaction with 9 steps 1: 90 percent / p-TsOH / 2 h / Heating 2: 86 percent / L-Selectride / tetrahydrofuran / 0.5 h / -78 °C 3: 78 percent / iodobenzene diacetate; I2 / cyclohexane / Photolysis 4: 30 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / benzene / Heating 5: 85 percent / K2CO3 / methanol / 20 °C 6: 78 percent / 4-DMAP / 3 h / 20 °C 7: 78 percent / t-BuOK / dimethylsulfoxide; tetrahydrofuran / 1 h / 0 °C 8: KBH4 / methanol / 1 h / 0 °C 9: 80 percent / imidazole / dimethylformamide / 18 h / 20 °C View Scheme | |
Multi-step reaction with 9 steps 1: 90 percent / p-TsOH / 2 h / Heating 2: 86 percent / L-Selectride / tetrahydrofuran / 0.5 h / -78 °C 3: 78 percent / iodobenzene diacetate; I2 / cyclohexane / Photolysis 4: 30 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / benzene / Heating 5: 85 percent / K2CO3 / methanol / 20 °C 6: 65 percent / Et3N / CH2Cl2 / 2 h / 0 °C 7: t-BuOK / tetrahydrofuran / 0 °C 8: KBH4 / methanol / 1 h / 0 °C 9: 80 percent / imidazole / dimethylformamide / 18 h / 20 °C View Scheme |
3aα-H-4α-(3’-propionic acid)-7aβ-methylhexahydro-1,5-indanedione
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 90 percent / p-TsOH / 2 h / Heating 2: 85 percent / KBH4 / methanol / 0.5 h / 0 °C 3: 85 percent / imidazole / dimethylformamide / 18 h / 20 °C View Scheme |
3aα-H-4α-(3’-propionic acid)-7aβ-methylhexahydro-1,5-indanedione
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: 90 percent / p-TsOH / 2 h / Heating 2: 85 percent / KBH4 / methanol / 0.5 h / 0 °C 3: 85 percent / imidazole / dimethylformamide / 18 h / 20 °C 4: DIBALH / CH2Cl2; hexane / 1 h / -78 °C View Scheme |
3aα-H-4α-(3’-propionic acid)-7aβ-methylhexahydro-1,5-indanedione
(3aS,7aS)-4α-ethenyl-1-oxo-5-(4'-methylbenzenesulfonyl)-3a,4,5,6,7,7a-hexahydro-7a-methylindan
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: 90 percent / p-TsOH / 2 h / Heating 2: 86 percent / L-Selectride / tetrahydrofuran / 0.5 h / -78 °C 3: 82 percent / Pb(OAc)4; Cu(OAc)2; pyridine / benzene / Heating 4: 85 percent / K2CO3 / methanol / 20 °C 5: 78 percent / 4-DMAP / 3 h / 20 °C View Scheme | |
Multi-step reaction with 6 steps 1: 90 percent / p-TsOH / 2 h / Heating 2: 86 percent / L-Selectride / tetrahydrofuran / 0.5 h / -78 °C 3: 78 percent / iodobenzene diacetate; I2 / cyclohexane / Photolysis 4: 30 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / benzene / Heating 5: 85 percent / K2CO3 / methanol / 20 °C 6: 78 percent / 4-DMAP / 3 h / 20 °C View Scheme |
3aα-H-4α-(3’-propionic acid)-7aβ-methylhexahydro-1,5-indanedione
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: 90 percent / p-TsOH / 2 h / Heating 2: 85 percent / KBH4 / methanol / 0.5 h / 0 °C 3: 85 percent / imidazole / dimethylformamide / 18 h / 20 °C 4: DIBALH / CH2Cl2; hexane / 1 h / -78 °C 5: 75 percent / I2; iodobenzene diacetate / cyclohexane / Photolysis View Scheme |
3aα-H-4α-(3’-propionic acid)-7aβ-methylhexahydro-1,5-indanedione
1β-hydroxy-3-trimethylsilylestra-1,3,5(10)-triene
Conditions | Yield |
---|---|
Multi-step reaction with 11 steps 1.1: 90 percent / p-TsOH / 2 h / Heating 2.1: 86 percent / L-Selectride / tetrahydrofuran / 0.5 h / -78 °C 3.1: 82 percent / Pb(OAc)4; Cu(OAc)2; pyridine / benzene / Heating 4.1: 85 percent / K2CO3 / methanol / 20 °C 5.1: 78 percent / 4-DMAP / 3 h / 20 °C 6.1: 78 percent / t-BuOK / dimethylsulfoxide; tetrahydrofuran / 1 h / 0 °C 7.1: KBH4 / methanol / 1 h / 0 °C 8.1: 80 percent / imidazole / dimethylformamide / 18 h / 20 °C 9.1: 70 percent / 1,2-dichloro-ethane / UV-irradiation 10.1: t-BuOK / tetrahydrofuran / 0.25 h / -105 °C 10.2: NCS / tetrahydrofuran / -105 - 25 °C 10.3: 60 percent / t-BuOK / tetrahydrofuran / 4 h / 20 °C 11.1: KNH(CH2)3NH2 / tetrahydrofuran / 15 h / 20 °C 11.2: 48 percent HF / acetonitrile / 20 °C 11.3: 45 percent / TFA; Et3SiH / benzene / 15 h / 20 °C View Scheme | |
Multi-step reaction with 11 steps 1.1: 90 percent / p-TsOH / 2 h / Heating 2.1: 86 percent / L-Selectride / tetrahydrofuran / 0.5 h / -78 °C 3.1: 82 percent / Pb(OAc)4; Cu(OAc)2; pyridine / benzene / Heating 4.1: 85 percent / K2CO3 / methanol / 20 °C 5.1: 65 percent / Et3N / CH2Cl2 / 2 h / 0 °C 6.1: t-BuOK / tetrahydrofuran / 0 °C 7.1: KBH4 / methanol / 1 h / 0 °C 8.1: 80 percent / imidazole / dimethylformamide / 18 h / 20 °C 9.1: 70 percent / 1,2-dichloro-ethane / UV-irradiation 10.1: t-BuOK / tetrahydrofuran / 0.25 h / -105 °C 10.2: NCS / tetrahydrofuran / -105 - 25 °C 10.3: 60 percent / t-BuOK / tetrahydrofuran / 4 h / 20 °C 11.1: KNH(CH2)3NH2 / tetrahydrofuran / 15 h / 20 °C 11.2: 48 percent HF / acetonitrile / 20 °C 11.3: 45 percent / TFA; Et3SiH / benzene / 15 h / 20 °C View Scheme | |
Multi-step reaction with 12 steps 1.1: 90 percent / p-TsOH / 2 h / Heating 2.1: 86 percent / L-Selectride / tetrahydrofuran / 0.5 h / -78 °C 3.1: 78 percent / iodobenzene diacetate; I2 / cyclohexane / Photolysis 4.1: 30 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / benzene / Heating 5.1: 85 percent / K2CO3 / methanol / 20 °C 6.1: 78 percent / 4-DMAP / 3 h / 20 °C 7.1: 78 percent / t-BuOK / dimethylsulfoxide; tetrahydrofuran / 1 h / 0 °C 8.1: KBH4 / methanol / 1 h / 0 °C 9.1: 80 percent / imidazole / dimethylformamide / 18 h / 20 °C 10.1: 70 percent / 1,2-dichloro-ethane / UV-irradiation 11.1: t-BuOK / tetrahydrofuran / 0.25 h / -105 °C 11.2: NCS / tetrahydrofuran / -105 - 25 °C 11.3: 60 percent / t-BuOK / tetrahydrofuran / 4 h / 20 °C 12.1: KNH(CH2)3NH2 / tetrahydrofuran / 15 h / 20 °C 12.2: 48 percent HF / acetonitrile / 20 °C 12.3: 45 percent / TFA; Et3SiH / benzene / 15 h / 20 °C View Scheme | |
Multi-step reaction with 12 steps 1.1: 90 percent / p-TsOH / 2 h / Heating 2.1: 86 percent / L-Selectride / tetrahydrofuran / 0.5 h / -78 °C 3.1: 78 percent / iodobenzene diacetate; I2 / cyclohexane / Photolysis 4.1: 30 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / benzene / Heating 5.1: 85 percent / K2CO3 / methanol / 20 °C 6.1: 65 percent / Et3N / CH2Cl2 / 2 h / 0 °C 7.1: t-BuOK / tetrahydrofuran / 0 °C 8.1: KBH4 / methanol / 1 h / 0 °C 9.1: 80 percent / imidazole / dimethylformamide / 18 h / 20 °C 10.1: 70 percent / 1,2-dichloro-ethane / UV-irradiation 11.1: t-BuOK / tetrahydrofuran / 0.25 h / -105 °C 11.2: NCS / tetrahydrofuran / -105 - 25 °C 11.3: 60 percent / t-BuOK / tetrahydrofuran / 4 h / 20 °C 12.1: KNH(CH2)3NH2 / tetrahydrofuran / 15 h / 20 °C 12.2: 48 percent HF / acetonitrile / 20 °C 12.3: 45 percent / TFA; Et3SiH / benzene / 15 h / 20 °C View Scheme |
3aα-H-4α-(3’-propionic acid)-7aβ-methylhexahydro-1,5-indanedione
Conditions | Yield |
---|---|
Multi-step reaction with 11 steps 1.1: 90 percent / p-TsOH / 2 h / Heating 2.1: 86 percent / L-Selectride / tetrahydrofuran / 0.5 h / -78 °C 3.1: 82 percent / Pb(OAc)4; Cu(OAc)2; pyridine / benzene / Heating 4.1: 85 percent / K2CO3 / methanol / 20 °C 5.1: 78 percent / 4-DMAP / 3 h / 20 °C 6.1: 78 percent / t-BuOK / dimethylsulfoxide; tetrahydrofuran / 1 h / 0 °C 7.1: KBH4 / methanol / 1 h / 0 °C 8.1: 80 percent / imidazole / dimethylformamide / 18 h / 20 °C 9.1: 70 percent / 1,2-dichloro-ethane / UV-irradiation 10.1: t-BuOK / tetrahydrofuran / 0.25 h / -105 °C 10.2: NCS / tetrahydrofuran / -105 - 25 °C 10.3: 60 percent / t-BuOK / tetrahydrofuran / 4 h / 20 °C 11.1: potassium 3-aminopropylamide / tetrahydrofuran / 15 h / 20 °C View Scheme | |
Multi-step reaction with 11 steps 1.1: 90 percent / p-TsOH / 2 h / Heating 2.1: 86 percent / L-Selectride / tetrahydrofuran / 0.5 h / -78 °C 3.1: 82 percent / Pb(OAc)4; Cu(OAc)2; pyridine / benzene / Heating 4.1: 85 percent / K2CO3 / methanol / 20 °C 5.1: 65 percent / Et3N / CH2Cl2 / 2 h / 0 °C 6.1: t-BuOK / tetrahydrofuran / 0 °C 7.1: KBH4 / methanol / 1 h / 0 °C 8.1: 80 percent / imidazole / dimethylformamide / 18 h / 20 °C 9.1: 70 percent / 1,2-dichloro-ethane / UV-irradiation 10.1: t-BuOK / tetrahydrofuran / 0.25 h / -105 °C 10.2: NCS / tetrahydrofuran / -105 - 25 °C 10.3: 60 percent / t-BuOK / tetrahydrofuran / 4 h / 20 °C 11.1: potassium 3-aminopropylamide / tetrahydrofuran / 15 h / 20 °C View Scheme | |
Multi-step reaction with 12 steps 1.1: 90 percent / p-TsOH / 2 h / Heating 2.1: 86 percent / L-Selectride / tetrahydrofuran / 0.5 h / -78 °C 3.1: 78 percent / iodobenzene diacetate; I2 / cyclohexane / Photolysis 4.1: 30 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / benzene / Heating 5.1: 85 percent / K2CO3 / methanol / 20 °C 6.1: 78 percent / 4-DMAP / 3 h / 20 °C 7.1: 78 percent / t-BuOK / dimethylsulfoxide; tetrahydrofuran / 1 h / 0 °C 8.1: KBH4 / methanol / 1 h / 0 °C 9.1: 80 percent / imidazole / dimethylformamide / 18 h / 20 °C 10.1: 70 percent / 1,2-dichloro-ethane / UV-irradiation 11.1: t-BuOK / tetrahydrofuran / 0.25 h / -105 °C 11.2: NCS / tetrahydrofuran / -105 - 25 °C 11.3: 60 percent / t-BuOK / tetrahydrofuran / 4 h / 20 °C 12.1: potassium 3-aminopropylamide / tetrahydrofuran / 15 h / 20 °C View Scheme | |
Multi-step reaction with 12 steps 1.1: 90 percent / p-TsOH / 2 h / Heating 2.1: 86 percent / L-Selectride / tetrahydrofuran / 0.5 h / -78 °C 3.1: 78 percent / iodobenzene diacetate; I2 / cyclohexane / Photolysis 4.1: 30 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / benzene / Heating 5.1: 85 percent / K2CO3 / methanol / 20 °C 6.1: 65 percent / Et3N / CH2Cl2 / 2 h / 0 °C 7.1: t-BuOK / tetrahydrofuran / 0 °C 8.1: KBH4 / methanol / 1 h / 0 °C 9.1: 80 percent / imidazole / dimethylformamide / 18 h / 20 °C 10.1: 70 percent / 1,2-dichloro-ethane / UV-irradiation 11.1: t-BuOK / tetrahydrofuran / 0.25 h / -105 °C 11.2: NCS / tetrahydrofuran / -105 - 25 °C 11.3: 60 percent / t-BuOK / tetrahydrofuran / 4 h / 20 °C 12.1: potassium 3-aminopropylamide / tetrahydrofuran / 15 h / 20 °C View Scheme |
3aα-H-4α-(3’-propionic acid)-7aβ-methylhexahydro-1,5-indanedione
1-[(tert-butyldimethylsilyl)oxy]-3-trimethylsilyl-9Hβ-estra-1,3,5(10),7-tetraene
Conditions | Yield |
---|---|
Multi-step reaction with 10 steps 1.1: 90 percent / p-TsOH / 2 h / Heating 2.1: 86 percent / L-Selectride / tetrahydrofuran / 0.5 h / -78 °C 3.1: 82 percent / Pb(OAc)4; Cu(OAc)2; pyridine / benzene / Heating 4.1: 85 percent / K2CO3 / methanol / 20 °C 5.1: 78 percent / 4-DMAP / 3 h / 20 °C 6.1: 78 percent / t-BuOK / dimethylsulfoxide; tetrahydrofuran / 1 h / 0 °C 7.1: KBH4 / methanol / 1 h / 0 °C 8.1: 80 percent / imidazole / dimethylformamide / 18 h / 20 °C 9.1: 70 percent / 1,2-dichloro-ethane / UV-irradiation 10.1: t-BuOK / tetrahydrofuran / 0.25 h / -105 °C 10.2: NCS / tetrahydrofuran / -105 - 25 °C 10.3: 60 percent / t-BuOK / tetrahydrofuran / 4 h / 20 °C View Scheme | |
Multi-step reaction with 10 steps 1.1: 90 percent / p-TsOH / 2 h / Heating 2.1: 86 percent / L-Selectride / tetrahydrofuran / 0.5 h / -78 °C 3.1: 82 percent / Pb(OAc)4; Cu(OAc)2; pyridine / benzene / Heating 4.1: 85 percent / K2CO3 / methanol / 20 °C 5.1: 65 percent / Et3N / CH2Cl2 / 2 h / 0 °C 6.1: t-BuOK / tetrahydrofuran / 0 °C 7.1: KBH4 / methanol / 1 h / 0 °C 8.1: 80 percent / imidazole / dimethylformamide / 18 h / 20 °C 9.1: 70 percent / 1,2-dichloro-ethane / UV-irradiation 10.1: t-BuOK / tetrahydrofuran / 0.25 h / -105 °C 10.2: NCS / tetrahydrofuran / -105 - 25 °C 10.3: 60 percent / t-BuOK / tetrahydrofuran / 4 h / 20 °C View Scheme | |
Multi-step reaction with 11 steps 1.1: 90 percent / p-TsOH / 2 h / Heating 2.1: 86 percent / L-Selectride / tetrahydrofuran / 0.5 h / -78 °C 3.1: 78 percent / iodobenzene diacetate; I2 / cyclohexane / Photolysis 4.1: 30 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / benzene / Heating 5.1: 85 percent / K2CO3 / methanol / 20 °C 6.1: 78 percent / 4-DMAP / 3 h / 20 °C 7.1: 78 percent / t-BuOK / dimethylsulfoxide; tetrahydrofuran / 1 h / 0 °C 8.1: KBH4 / methanol / 1 h / 0 °C 9.1: 80 percent / imidazole / dimethylformamide / 18 h / 20 °C 10.1: 70 percent / 1,2-dichloro-ethane / UV-irradiation 11.1: t-BuOK / tetrahydrofuran / 0.25 h / -105 °C 11.2: NCS / tetrahydrofuran / -105 - 25 °C 11.3: 60 percent / t-BuOK / tetrahydrofuran / 4 h / 20 °C View Scheme | |
Multi-step reaction with 11 steps 1.1: 90 percent / p-TsOH / 2 h / Heating 2.1: 86 percent / L-Selectride / tetrahydrofuran / 0.5 h / -78 °C 3.1: 78 percent / iodobenzene diacetate; I2 / cyclohexane / Photolysis 4.1: 30 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / benzene / Heating 5.1: 85 percent / K2CO3 / methanol / 20 °C 6.1: 65 percent / Et3N / CH2Cl2 / 2 h / 0 °C 7.1: t-BuOK / tetrahydrofuran / 0 °C 8.1: KBH4 / methanol / 1 h / 0 °C 9.1: 80 percent / imidazole / dimethylformamide / 18 h / 20 °C 10.1: 70 percent / 1,2-dichloro-ethane / UV-irradiation 11.1: t-BuOK / tetrahydrofuran / 0.25 h / -105 °C 11.2: NCS / tetrahydrofuran / -105 - 25 °C 11.3: 60 percent / t-BuOK / tetrahydrofuran / 4 h / 20 °C View Scheme |
3aα-H-4α-(3’-propionic acid)-7aβ-methylhexahydro-1,5-indanedione
Conditions | Yield |
---|---|
Multi-step reaction with 11 steps 1.1: 90 percent / p-TsOH / 2 h / Heating 2.1: 86 percent / L-Selectride / tetrahydrofuran / 0.5 h / -78 °C 3.1: 82 percent / Pb(OAc)4; Cu(OAc)2; pyridine / benzene / Heating 4.1: 85 percent / K2CO3 / methanol / 20 °C 5.1: 78 percent / 4-DMAP / 3 h / 20 °C 6.1: 78 percent / t-BuOK / dimethylsulfoxide; tetrahydrofuran / 1 h / 0 °C 7.1: KBH4 / methanol / 1 h / 0 °C 8.1: 80 percent / imidazole / dimethylformamide / 18 h / 20 °C 9.1: 70 percent / 1,2-dichloro-ethane / UV-irradiation 10.1: t-BuOK / tetrahydrofuran / 0.25 h / -105 °C 10.2: NCS / tetrahydrofuran / -105 - 25 °C 10.3: 60 percent / t-BuOK / tetrahydrofuran / 4 h / 20 °C 11.1: potassium 3-aminopropylamide / tetrahydrofuran / 15 h / 20 °C View Scheme | |
Multi-step reaction with 11 steps 1.1: 90 percent / p-TsOH / 2 h / Heating 2.1: 86 percent / L-Selectride / tetrahydrofuran / 0.5 h / -78 °C 3.1: 82 percent / Pb(OAc)4; Cu(OAc)2; pyridine / benzene / Heating 4.1: 85 percent / K2CO3 / methanol / 20 °C 5.1: 65 percent / Et3N / CH2Cl2 / 2 h / 0 °C 6.1: t-BuOK / tetrahydrofuran / 0 °C 7.1: KBH4 / methanol / 1 h / 0 °C 8.1: 80 percent / imidazole / dimethylformamide / 18 h / 20 °C 9.1: 70 percent / 1,2-dichloro-ethane / UV-irradiation 10.1: t-BuOK / tetrahydrofuran / 0.25 h / -105 °C 10.2: NCS / tetrahydrofuran / -105 - 25 °C 10.3: 60 percent / t-BuOK / tetrahydrofuran / 4 h / 20 °C 11.1: potassium 3-aminopropylamide / tetrahydrofuran / 15 h / 20 °C View Scheme | |
Multi-step reaction with 12 steps 1.1: 90 percent / p-TsOH / 2 h / Heating 2.1: 86 percent / L-Selectride / tetrahydrofuran / 0.5 h / -78 °C 3.1: 78 percent / iodobenzene diacetate; I2 / cyclohexane / Photolysis 4.1: 30 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / benzene / Heating 5.1: 85 percent / K2CO3 / methanol / 20 °C 6.1: 78 percent / 4-DMAP / 3 h / 20 °C 7.1: 78 percent / t-BuOK / dimethylsulfoxide; tetrahydrofuran / 1 h / 0 °C 8.1: KBH4 / methanol / 1 h / 0 °C 9.1: 80 percent / imidazole / dimethylformamide / 18 h / 20 °C 10.1: 70 percent / 1,2-dichloro-ethane / UV-irradiation 11.1: t-BuOK / tetrahydrofuran / 0.25 h / -105 °C 11.2: NCS / tetrahydrofuran / -105 - 25 °C 11.3: 60 percent / t-BuOK / tetrahydrofuran / 4 h / 20 °C 12.1: potassium 3-aminopropylamide / tetrahydrofuran / 15 h / 20 °C View Scheme | |
Multi-step reaction with 12 steps 1.1: 90 percent / p-TsOH / 2 h / Heating 2.1: 86 percent / L-Selectride / tetrahydrofuran / 0.5 h / -78 °C 3.1: 78 percent / iodobenzene diacetate; I2 / cyclohexane / Photolysis 4.1: 30 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / benzene / Heating 5.1: 85 percent / K2CO3 / methanol / 20 °C 6.1: 65 percent / Et3N / CH2Cl2 / 2 h / 0 °C 7.1: t-BuOK / tetrahydrofuran / 0 °C 8.1: KBH4 / methanol / 1 h / 0 °C 9.1: 80 percent / imidazole / dimethylformamide / 18 h / 20 °C 10.1: 70 percent / 1,2-dichloro-ethane / UV-irradiation 11.1: t-BuOK / tetrahydrofuran / 0.25 h / -105 °C 11.2: NCS / tetrahydrofuran / -105 - 25 °C 11.3: 60 percent / t-BuOK / tetrahydrofuran / 4 h / 20 °C 12.1: potassium 3-aminopropylamide / tetrahydrofuran / 15 h / 20 °C View Scheme |
3aα-H-4α-(3’-propionic acid)-7aβ-methylhexahydro-1,5-indanedione
(1S,2S,5S,9S,13S)-6-[(tert-butyldimethylsilyl)oxy]-5-methyl-15-trimethylsilyl-18-thiatetracyclo[11.4.1.02,10.05,9]-10,14,16-triene-18,18-dioxide
Conditions | Yield |
---|---|
Multi-step reaction with 9 steps 1: 90 percent / p-TsOH / 2 h / Heating 2: 86 percent / L-Selectride / tetrahydrofuran / 0.5 h / -78 °C 3: 82 percent / Pb(OAc)4; Cu(OAc)2; pyridine / benzene / Heating 4: 85 percent / K2CO3 / methanol / 20 °C 5: 78 percent / 4-DMAP / 3 h / 20 °C 6: 78 percent / t-BuOK / dimethylsulfoxide; tetrahydrofuran / 1 h / 0 °C 7: KBH4 / methanol / 1 h / 0 °C 8: 80 percent / imidazole / dimethylformamide / 18 h / 20 °C 9: 70 percent / 1,2-dichloro-ethane / UV-irradiation View Scheme | |
Multi-step reaction with 9 steps 1: 90 percent / p-TsOH / 2 h / Heating 2: 86 percent / L-Selectride / tetrahydrofuran / 0.5 h / -78 °C 3: 82 percent / Pb(OAc)4; Cu(OAc)2; pyridine / benzene / Heating 4: 85 percent / K2CO3 / methanol / 20 °C 5: 65 percent / Et3N / CH2Cl2 / 2 h / 0 °C 6: t-BuOK / tetrahydrofuran / 0 °C 7: KBH4 / methanol / 1 h / 0 °C 8: 80 percent / imidazole / dimethylformamide / 18 h / 20 °C 9: 70 percent / 1,2-dichloro-ethane / UV-irradiation View Scheme | |
Multi-step reaction with 10 steps 1: 90 percent / p-TsOH / 2 h / Heating 2: 86 percent / L-Selectride / tetrahydrofuran / 0.5 h / -78 °C 3: 78 percent / iodobenzene diacetate; I2 / cyclohexane / Photolysis 4: 30 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / benzene / Heating 5: 85 percent / K2CO3 / methanol / 20 °C 6: 78 percent / 4-DMAP / 3 h / 20 °C 7: 78 percent / t-BuOK / dimethylsulfoxide; tetrahydrofuran / 1 h / 0 °C 8: KBH4 / methanol / 1 h / 0 °C 9: 80 percent / imidazole / dimethylformamide / 18 h / 20 °C 10: 70 percent / 1,2-dichloro-ethane / UV-irradiation View Scheme | |
Multi-step reaction with 10 steps 1: 90 percent / p-TsOH / 2 h / Heating 2: 86 percent / L-Selectride / tetrahydrofuran / 0.5 h / -78 °C 3: 78 percent / iodobenzene diacetate; I2 / cyclohexane / Photolysis 4: 30 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / benzene / Heating 5: 85 percent / K2CO3 / methanol / 20 °C 6: 65 percent / Et3N / CH2Cl2 / 2 h / 0 °C 7: t-BuOK / tetrahydrofuran / 0 °C 8: KBH4 / methanol / 1 h / 0 °C 9: 80 percent / imidazole / dimethylformamide / 18 h / 20 °C 10: 70 percent / 1,2-dichloro-ethane / UV-irradiation View Scheme |
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