DayangChem exported this product to many countries and regions at best price. If you are looking for the material's manufacturer or supplier in China, DayangChem is your best choice. Pls contact with us freely for getting detailed product spe
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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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inquiryWITH 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
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inquiryBest quality & Attractive price & Professional service; Trial & Pilot & Commercial Hisunny Chemical is a leading manufacturer and supplier of chemicals in China. We develop produce and distribute high quality intermediates, specia
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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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inquiryJ&H CHEM R&D center can offer custom synthesis according to the contract research and development services for the fine chemicals, pharmaceutical, biotechnique and some of the other chemicals. J&H CHEM has some Manufacturing base in Jia
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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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inquiry2-(3-Methoxypropoxy)-4-((R)-2-(bromomethyl)-3-methylbutyl)-1-methoxybenzene Basic information Product Name: 2-(3-Methoxypropoxy)-4-((R)-2-(bromomethyl)-3-methylbutyl)-1-methoxybenzene Synonyms: 2-(3-methoxypropoxy)-4-((R)-2-(bromomethyl)-3-methyl
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inquiryHunan chemfish Pharmaceutical co.,Ltd.located in Lugu High-tech industral park ,Hunan province . with its own R&D center and more than 10000㎡manufacture plant . Chemfish owns 40 reactors from 1000L to 8000L. With complete auxiliary equipment as
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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
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inquiryHigh quality,stable supply chain.Appearance:white/off-white or light yellow Storage:Store in cool and dry place, keep away from strong light and heat. Package:aluminum bottle,glass bottle,PTFE bottle,cardboard drum Application:This product can be use
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inquiryGOLDEN PHARMA CO.,LIMITED.is a professional pharmaceutical company,our team have more than 20years expereince in pharmaceutical production and sales. we are a professional technical enterprise specializing in the R & D, production,QA regulation
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inquiryR & D enterprises have their own stock in stockAppearance:To be subject to the object Package:Customized Application:pharmaceutical intermediates Transportation:Air Port:Shanghai;Guangzhou
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inquiryhigh purity,in stock Package:25kg/drum,or as per customers'demand Application:API,Pharmaceutical intermediates Transportation:air,sea,courier
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inquiryhigh quality Storage:Sealed, dry, microtherm , avoid light and smell. Package:According to the demand of customer Application:Organic synthesis Transportation:by air or by sea
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inquiryOur clients, like BASF,CHEMO,Brenntag,ASR,Evonik,Merck and etc.Appearance:COA Storage:in stock Application:MSDS/TDS
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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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inquiry2-(3-Methoxypropoxy)-4-((R)-2-(bromomethyl)-3-methylbutyl)-1-methoxybenzene cas 172900-69-5Appearance:white crystalline powder Storage:Store in dry, dark and ventilated place Package:25KG drum Application:intermediate Transportation:by air, by sea,
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inquiry172900-69-5 Application:intermediate
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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:any port in China
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inquiry1.Professional synthesis laboratory and production base. 2.Strong synthesis team and service team. 3.Professional data management system. 4.We provide the professional test date and product information ,ex. HNMR ,CNMR,FNMR, HPLC/G
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inquiry(R)-2-[4-methoxy-3-(3-methoxypropoxy)benzyl]-3-methylbutanol
(R)-4-(2-(bromomethyl)-3-methylbutyl)-1-methoxy-2-(3-methoxypropoxy)benzene
Conditions | Yield |
---|---|
With N-Bromosuccinimide; triphenylphosphine In dichloromethane at 20℃; for 18h; | 97% |
With N-Bromosuccinimide; triphenylphosphine In dichloromethane | 97% |
With phosphorus(V) oxybromide In N,N-dimethyl-formamide at 20℃; for 8h; Temperature; Time; Solvent; | 79.6% |
isovanillin
(R)-4-(2-(bromomethyl)-3-methylbutyl)-1-methoxy-2-(3-methoxypropoxy)benzene
Conditions | Yield |
---|---|
Multi-step reaction with 7 steps 1: 98 percent / K2CO3 / acetonitrile 2: NaBH4 / ethanol 3: PBr3 / CH2Cl2 4: 76 percent / LiHMDS / tetrahydrofuran 5: 81 percent / LiOH; H2O2 6: 95 percent / LAH / tetrahydrofuran 7: 97 percent / PPh3; NBS / CH2Cl2 View Scheme | |
Multi-step reaction with 8 steps 1.1: 93 percent / K2CO3 / acetonitrile / 19 h / Heating 2.1: 72 percent / NaOMe / methanol / 1.5 h / Heating 3.1: 96 percent / NaBH4 / methanol / 1 h / 20 °C 4.1: 100 percent / Me3SiBr / 0.17 h / 20 °C 5.1: LiHMDS / tetrahydrofuran / 1.25 h / -70 °C 5.2: 86 percent / tetrahydrofuran / 18 h / 0 °C 6.1: 94 percent / H2O2; LiOH / tetrahydrofuran; H2O / 3 h / 20 °C 7.1: NaBH4 / tetrahydrofuran / 0.75 h / 20 °C 7.2: 90 percent / I2 / tetrahydrofuran / 96 h / 20 °C 8.1: 97 percent / NBS; Ph3P / CH2Cl2 / 18 h / 20 °C View Scheme | |
Multi-step reaction with 7 steps 1.1: potassium carbonate; N-benzyl-N,N,N-triethylammonium chloride / acetonitrile / Reflux 2.1: potassium borohydride / methanol / 20 °C 3.1: phosphorus tribromide / dichloromethane / 2 h / 20 °C 4.1: lithium hexamethyldisilazane / tetrahydrofuran / 1.17 h / 70 °C / Inert atmosphere 4.2: 0 - 70 °C / Inert atmosphere 5.1: dihydrogen peroxide; lithium hydroxide monohydrate / tetrahydrofuran; water / 0 - 20 °C 6.1: sodium tetrahydroborate; boron trifluoride diethyl etherate / tetrahydrofuran / 5 h / 20 °C / Inert atmosphere 7.1: phosphorus tribromide / dichloromethane / 0 °C View Scheme |
(R)-4-benzyl-3-(3-methylbutyryl)oxazolidin-2-one
(R)-4-(2-(bromomethyl)-3-methylbutyl)-1-methoxy-2-(3-methoxypropoxy)benzene
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: 76 percent / LiHMDS / tetrahydrofuran 2: 81 percent / LiOH; H2O2 3: 95 percent / LAH / tetrahydrofuran 4: 97 percent / PPh3; NBS / CH2Cl2 View Scheme | |
Multi-step reaction with 4 steps 1.1: lithium hexamethyldisilazane / tetrahydrofuran / 1.17 h / 70 °C / Inert atmosphere 1.2: 0 - 70 °C / Inert atmosphere 2.1: dihydrogen peroxide; lithium hydroxide monohydrate / tetrahydrofuran; water / 0 - 20 °C 3.1: sodium tetrahydroborate; boron trifluoride diethyl etherate / tetrahydrofuran / 5 h / 20 °C / Inert atmosphere 4.1: phosphorus tribromide / dichloromethane / 0 °C View Scheme |
4-methoxy-3-(3-methoxypropoxy)benzaldehyde
(R)-4-(2-(bromomethyl)-3-methylbutyl)-1-methoxy-2-(3-methoxypropoxy)benzene
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1: NaBH4 / ethanol 2: PBr3 / CH2Cl2 3: 76 percent / LiHMDS / tetrahydrofuran 4: 81 percent / LiOH; H2O2 5: 95 percent / LAH / tetrahydrofuran 6: 97 percent / PPh3; NBS / CH2Cl2 View Scheme | |
Multi-step reaction with 6 steps 1.1: 96 percent / NaBH4 / methanol / 1 h / 20 °C 2.1: 100 percent / Me3SiBr / 0.17 h / 20 °C 3.1: LiHMDS / tetrahydrofuran / 1.25 h / -70 °C 3.2: 86 percent / tetrahydrofuran / 18 h / 0 °C 4.1: 94 percent / H2O2; LiOH / tetrahydrofuran; H2O / 3 h / 20 °C 5.1: NaBH4 / tetrahydrofuran / 0.75 h / 20 °C 5.2: 90 percent / I2 / tetrahydrofuran / 96 h / 20 °C 6.1: 97 percent / NBS; Ph3P / CH2Cl2 / 18 h / 20 °C View Scheme | |
Multi-step reaction with 6 steps 1.1: sodium tetrahydroborate / tetrahydrofuran / 0 - 30 °C 1.2: pH 2 2.1: phosphorus tribromide / dichloromethane / 2.17 h / 0 - 5 °C 3.1: lithium hexamethyldisilazane / tetrahydrofuran / 2 h / -70 °C / Inert atmosphere 3.2: -70 - 5 °C 4.1: dihydrogen peroxide; lithium hydroxide monohydrate / water; tetrahydrofuran / 0 - 30 °C 5.1: sodium tetrahydroborate / tetrahydrofuran / 1 h / 0 - 5 °C / Inert atmosphere 5.2: 5.75 h / 0 - 30 °C 6.1: triphenylphosphine; N-Bromosuccinimide / dichloromethane / 5.5 h / -40 - 30 °C View Scheme |
(R)-3-[4-methoxy-3-(3-methoxypropoxy)phenyl]-2-(1-methylethyl)propanoic acid
(R)-4-(2-(bromomethyl)-3-methylbutyl)-1-methoxy-2-(3-methoxypropoxy)benzene
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 95 percent / LAH / tetrahydrofuran 2: 97 percent / PPh3; NBS / CH2Cl2 View Scheme | |
Multi-step reaction with 2 steps 1.1: NaBH4 / tetrahydrofuran / 0.75 h / 20 °C 1.2: 90 percent / I2 / tetrahydrofuran / 96 h / 20 °C 2.1: 97 percent / NBS; Ph3P / CH2Cl2 / 18 h / 20 °C View Scheme | |
Multi-step reaction with 2 steps 1.1: sodium tetrahydroborate / tetrahydrofuran / 1 h / 0 - 5 °C / Inert atmosphere 1.2: 5.75 h / 0 - 30 °C 2.1: triphenylphosphine; N-Bromosuccinimide / dichloromethane / 5.5 h / -40 - 30 °C View Scheme | |
Multi-step reaction with 2 steps 1: sodium tetrahydroborate; boron trifluoride diethyl etherate / tetrahydrofuran / 5 h / 20 °C / Inert atmosphere 2: phosphorus tribromide / dichloromethane / 0 °C View Scheme |
4-(bromomethyl)-1-methoxy-2-(3-methoxypropoxy)-benzene
(R)-4-(2-(bromomethyl)-3-methylbutyl)-1-methoxy-2-(3-methoxypropoxy)benzene
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: 76 percent / LiHMDS / tetrahydrofuran 2: 81 percent / LiOH; H2O2 3: 95 percent / LAH / tetrahydrofuran 4: 97 percent / PPh3; NBS / CH2Cl2 View Scheme | |
Multi-step reaction with 4 steps 1.1: LiHMDS / tetrahydrofuran / 1.25 h / -70 °C 1.2: 86 percent / tetrahydrofuran / 18 h / 0 °C 2.1: 94 percent / H2O2; LiOH / tetrahydrofuran; H2O / 3 h / 20 °C 3.1: NaBH4 / tetrahydrofuran / 0.75 h / 20 °C 3.2: 90 percent / I2 / tetrahydrofuran / 96 h / 20 °C 4.1: 97 percent / NBS; Ph3P / CH2Cl2 / 18 h / 20 °C View Scheme | |
Multi-step reaction with 4 steps 1.1: lithium hexamethyldisilazane / tetrahydrofuran / 2 h / -70 °C / Inert atmosphere 1.2: -70 - 5 °C 2.1: dihydrogen peroxide; lithium hydroxide monohydrate / water; tetrahydrofuran / 0 - 30 °C 3.1: sodium tetrahydroborate / tetrahydrofuran / 1 h / 0 - 5 °C / Inert atmosphere 3.2: 5.75 h / 0 - 30 °C 4.1: triphenylphosphine; N-Bromosuccinimide / dichloromethane / 5.5 h / -40 - 30 °C View Scheme |
[4-methoxy-3-(3-methoxypropoxy)-phenyl]methanol
(R)-4-(2-(bromomethyl)-3-methylbutyl)-1-methoxy-2-(3-methoxypropoxy)benzene
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: PBr3 / CH2Cl2 2: 76 percent / LiHMDS / tetrahydrofuran 3: 81 percent / LiOH; H2O2 4: 95 percent / LAH / tetrahydrofuran 5: 97 percent / PPh3; NBS / CH2Cl2 View Scheme | |
Multi-step reaction with 5 steps 1.1: 100 percent / Me3SiBr / 0.17 h / 20 °C 2.1: LiHMDS / tetrahydrofuran / 1.25 h / -70 °C 2.2: 86 percent / tetrahydrofuran / 18 h / 0 °C 3.1: 94 percent / H2O2; LiOH / tetrahydrofuran; H2O / 3 h / 20 °C 4.1: NaBH4 / tetrahydrofuran / 0.75 h / 20 °C 4.2: 90 percent / I2 / tetrahydrofuran / 96 h / 20 °C 5.1: 97 percent / NBS; Ph3P / CH2Cl2 / 18 h / 20 °C View Scheme | |
Multi-step reaction with 5 steps 1.1: phosphorus tribromide / dichloromethane / 2.17 h / 0 - 5 °C 2.1: lithium hexamethyldisilazane / tetrahydrofuran / 2 h / -70 °C / Inert atmosphere 2.2: -70 - 5 °C 3.1: dihydrogen peroxide; lithium hydroxide monohydrate / water; tetrahydrofuran / 0 - 30 °C 4.1: sodium tetrahydroborate / tetrahydrofuran / 1 h / 0 - 5 °C / Inert atmosphere 4.2: 5.75 h / 0 - 30 °C 5.1: triphenylphosphine; N-Bromosuccinimide / dichloromethane / 5.5 h / -40 - 30 °C View Scheme |
(4R)-3-{(2R)-2-{[4-methoxy-3-(methoxypropoxy)phenyl]methyl-3-methyl}-1-oxobutyl}-4-(phenylmethyl)oxazolidin-2-one
(R)-4-(2-(bromomethyl)-3-methylbutyl)-1-methoxy-2-(3-methoxypropoxy)benzene
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 81 percent / LiOH; H2O2 2: 95 percent / LAH / tetrahydrofuran 3: 97 percent / PPh3; NBS / CH2Cl2 View Scheme | |
Multi-step reaction with 3 steps 1.1: 94 percent / H2O2; LiOH / tetrahydrofuran; H2O / 3 h / 20 °C 2.1: NaBH4 / tetrahydrofuran / 0.75 h / 20 °C 2.2: 90 percent / I2 / tetrahydrofuran / 96 h / 20 °C 3.1: 97 percent / NBS; Ph3P / CH2Cl2 / 18 h / 20 °C View Scheme | |
Multi-step reaction with 3 steps 1: dihydrogen peroxide; lithium hydroxide monohydrate / tetrahydrofuran; water / 0 - 20 °C 2: sodium tetrahydroborate; boron trifluoride diethyl etherate / tetrahydrofuran / 5 h / 20 °C / Inert atmosphere 3: phosphorus tribromide / dichloromethane / 0 °C View Scheme |
3-(3-bromopropoxy)-4-methoxybenzaldehyde
(R)-4-(2-(bromomethyl)-3-methylbutyl)-1-methoxy-2-(3-methoxypropoxy)benzene
Conditions | Yield |
---|---|
Multi-step reaction with 7 steps 1.1: 72 percent / NaOMe / methanol / 1.5 h / Heating 2.1: 96 percent / NaBH4 / methanol / 1 h / 20 °C 3.1: 100 percent / Me3SiBr / 0.17 h / 20 °C 4.1: LiHMDS / tetrahydrofuran / 1.25 h / -70 °C 4.2: 86 percent / tetrahydrofuran / 18 h / 0 °C 5.1: 94 percent / H2O2; LiOH / tetrahydrofuran; H2O / 3 h / 20 °C 6.1: NaBH4 / tetrahydrofuran / 0.75 h / 20 °C 6.2: 90 percent / I2 / tetrahydrofuran / 96 h / 20 °C 7.1: 97 percent / NBS; Ph3P / CH2Cl2 / 18 h / 20 °C View Scheme |
3-methylbutyric acid
(R)-4-(2-(bromomethyl)-3-methylbutyl)-1-methoxy-2-(3-methoxypropoxy)benzene
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1.1: dmap / 1,1-dichloroethane / 0.5 h / 20 °C 1.2: 14.5 h / 10 - 30 °C 2.1: lithium hexamethyldisilazane / tetrahydrofuran / 2 h / -70 °C / Inert atmosphere 2.2: -70 - 5 °C 3.1: dihydrogen peroxide; lithium hydroxide monohydrate / water; tetrahydrofuran / 0 - 30 °C 4.1: sodium tetrahydroborate / tetrahydrofuran / 1 h / 0 - 5 °C / Inert atmosphere 4.2: 5.75 h / 0 - 30 °C 5.1: triphenylphosphine; N-Bromosuccinimide / dichloromethane / 5.5 h / -40 - 30 °C View Scheme | |
Multi-step reaction with 4 steps 1.1: dmap / 1,1-dichloroethane / 0.5 h / 20 °C 1.2: 14.5 h / 10 - 30 °C 2.1: lithium hexamethyldisilazane / tetrahydrofuran / 2 h / -70 °C / Inert atmosphere 2.2: -70 - 5 °C 3.1: sodium tetrahydroborate / tetrahydrofuran / 0 - 15 °C 3.2: 11 h / 60 - 65 °C 4.1: triphenylphosphine; N-Bromosuccinimide / dichloromethane / 5.5 h / -40 - 30 °C View Scheme | |
Multi-step reaction with 5 steps 1.1: dmap / 1,1-dichloroethane / 0.5 h / 20 °C 1.2: 14.5 h / 10 - 30 °C 2.1: titanium(IV) isopropylate; N-ethyl-N,N-diisopropylamine; titanium tetrachloride / dichloromethane / 1 h / 0 - 5 °C / Inert atmosphere 2.2: -30 - -25 °C 2.3: -30 - 5 °C 3.1: hydrogen; acetic acid / palladium on activated charcoal / 60 - 70 °C / 2942.29 Torr 4.1: sodium tetrahydroborate / tetrahydrofuran / 0 - 15 °C 4.2: 11 h / 60 - 65 °C 5.1: triphenylphosphine; N-Bromosuccinimide / dichloromethane / 5.5 h / -40 - 30 °C View Scheme | |
Multi-step reaction with 6 steps 1.1: dmap / 1,1-dichloroethane / 0.5 h / 20 °C 1.2: 14.5 h / 10 - 30 °C 2.1: titanium(IV) isopropylate; N-ethyl-N,N-diisopropylamine; titanium tetrachloride / dichloromethane / 1 h / 0 - 5 °C / Inert atmosphere 2.2: -30 - -25 °C 2.3: -30 - 5 °C 3.1: hydrogen; acetic acid / palladium on activated charcoal / 60 - 70 °C / 2942.29 Torr 4.1: dihydrogen peroxide; lithium hydroxide monohydrate / water; tetrahydrofuran / 0 - 30 °C 5.1: sodium tetrahydroborate / tetrahydrofuran / 1 h / 0 - 5 °C / Inert atmosphere 5.2: 5.75 h / 0 - 30 °C 6.1: triphenylphosphine; N-Bromosuccinimide / dichloromethane / 5.5 h / -40 - 30 °C View Scheme |
(R)-4-(2-(bromomethyl)-3-methylbutyl)-1-methoxy-2-(3-methoxypropoxy)benzene
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1.1: lithium hexamethyldisilazane / tetrahydrofuran / 2 h / -70 °C / Inert atmosphere 1.2: -70 - 5 °C 2.1: dihydrogen peroxide; lithium hydroxide monohydrate / water; tetrahydrofuran / 0 - 30 °C 3.1: sodium tetrahydroborate / tetrahydrofuran / 1 h / 0 - 5 °C / Inert atmosphere 3.2: 5.75 h / 0 - 30 °C 4.1: triphenylphosphine; N-Bromosuccinimide / dichloromethane / 5.5 h / -40 - 30 °C View Scheme | |
Multi-step reaction with 3 steps 1.1: lithium hexamethyldisilazane / tetrahydrofuran / 2 h / -70 °C / Inert atmosphere 1.2: -70 - 5 °C 2.1: sodium tetrahydroborate / tetrahydrofuran / 0 - 15 °C 2.2: 11 h / 60 - 65 °C 3.1: triphenylphosphine; N-Bromosuccinimide / dichloromethane / 5.5 h / -40 - 30 °C View Scheme | |
Multi-step reaction with 4 steps 1.1: titanium(IV) isopropylate; N-ethyl-N,N-diisopropylamine; titanium tetrachloride / dichloromethane / 1 h / 0 - 5 °C / Inert atmosphere 1.2: -30 - -25 °C 1.3: -30 - 5 °C 2.1: hydrogen; acetic acid / palladium on activated charcoal / 60 - 70 °C / 2942.29 Torr 3.1: sodium tetrahydroborate / tetrahydrofuran / 0 - 15 °C 3.2: 11 h / 60 - 65 °C 4.1: triphenylphosphine; N-Bromosuccinimide / dichloromethane / 5.5 h / -40 - 30 °C View Scheme | |
Multi-step reaction with 5 steps 1.1: titanium(IV) isopropylate; N-ethyl-N,N-diisopropylamine; titanium tetrachloride / dichloromethane / 1 h / 0 - 5 °C / Inert atmosphere 1.2: -30 - -25 °C 1.3: -30 - 5 °C 2.1: hydrogen; acetic acid / palladium on activated charcoal / 60 - 70 °C / 2942.29 Torr 3.1: dihydrogen peroxide; lithium hydroxide monohydrate / water; tetrahydrofuran / 0 - 30 °C 4.1: sodium tetrahydroborate / tetrahydrofuran / 1 h / 0 - 5 °C / Inert atmosphere 4.2: 5.75 h / 0 - 30 °C 5.1: triphenylphosphine; N-Bromosuccinimide / dichloromethane / 5.5 h / -40 - 30 °C View Scheme |
(R)-3-((R)-2-(4-methoxy-3-(3-methoxypropoxy)benzyl)-3-methylbutanoyl)-4-phenyloxazolidin-2-one
(R)-4-(2-(bromomethyl)-3-methylbutyl)-1-methoxy-2-(3-methoxypropoxy)benzene
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: dihydrogen peroxide; lithium hydroxide monohydrate / water; tetrahydrofuran / 0 - 30 °C 2.1: sodium tetrahydroborate / tetrahydrofuran / 1 h / 0 - 5 °C / Inert atmosphere 2.2: 5.75 h / 0 - 30 °C 3.1: triphenylphosphine; N-Bromosuccinimide / dichloromethane / 5.5 h / -40 - 30 °C View Scheme | |
Multi-step reaction with 2 steps 1.1: sodium tetrahydroborate / tetrahydrofuran / 0 - 15 °C 1.2: 11 h / 60 - 65 °C 2.1: triphenylphosphine; N-Bromosuccinimide / dichloromethane / 5.5 h / -40 - 30 °C View Scheme |
(4R)-3-(2S)-(2-(hydroxy(4-methoxy-3-(3-methoxypropoxy)phenyl)methyl)-3-methylbutanoyl)-4-phenyloxazolidin-2-one
(R)-4-(2-(bromomethyl)-3-methylbutyl)-1-methoxy-2-(3-methoxypropoxy)benzene
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1.1: hydrogen; acetic acid / palladium on activated charcoal / 60 - 70 °C / 2942.29 Torr 2.1: dihydrogen peroxide; lithium hydroxide monohydrate / water; tetrahydrofuran / 0 - 30 °C 3.1: sodium tetrahydroborate / tetrahydrofuran / 1 h / 0 - 5 °C / Inert atmosphere 3.2: 5.75 h / 0 - 30 °C 4.1: triphenylphosphine; N-Bromosuccinimide / dichloromethane / 5.5 h / -40 - 30 °C View Scheme | |
Multi-step reaction with 3 steps 1.1: hydrogen; acetic acid / palladium on activated charcoal / 60 - 70 °C / 2942.29 Torr 2.1: sodium tetrahydroborate / tetrahydrofuran / 0 - 15 °C 2.2: 11 h / 60 - 65 °C 3.1: triphenylphosphine; N-Bromosuccinimide / dichloromethane / 5.5 h / -40 - 30 °C View Scheme |
3-hydroxy-4-methoxybenzyl alcohol
(R)-4-(2-(bromomethyl)-3-methylbutyl)-1-methoxy-2-(3-methoxypropoxy)benzene
Conditions | Yield |
---|---|
Multi-step reaction with 7 steps 1.1: potassium carbonate / acetonitrile / 10 h / 25 - 35 °C / Reflux 2.1: phosphorus tribromide / dichloromethane / 2 h / 0 - 10 °C 3.1: toluene / 2 h / 85 - 90 °C 4.1: sodium hydroxide; water / ethanol / 72 h / Reflux 4.2: pH 1 - 1.2 4.3: 35 h / 155 °C 5.1: (S)-1-phenyl-ethylamine / ethyl acetate / 4 h / 10 °C 5.2: pH 1 - 1.2 6.1: sodium bis(2-methoxyethoxy)aluminium dihydride / toluene / 2 h / 20 °C 6.2: 5 °C 7.1: triphenylphosphine; N-Bromosuccinimide / dichloromethane / 4 h / 5 - 10 °C View Scheme |
2-isopropyl-3-{2-[3-methoxy(propyloxy)]-4-methoxyphenyl}propionic acid
(R)-4-(2-(bromomethyl)-3-methylbutyl)-1-methoxy-2-(3-methoxypropoxy)benzene
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: (S)-1-phenyl-ethylamine / ethyl acetate / 4 h / 10 °C 1.2: pH 1 - 1.2 2.1: sodium bis(2-methoxyethoxy)aluminium dihydride / toluene / 2 h / 20 °C 2.2: 5 °C 3.1: triphenylphosphine; N-Bromosuccinimide / dichloromethane / 4 h / 5 - 10 °C View Scheme |
dimethyl-2(4-methoxy-3-(3-methoxypropyloxy)-benzyl)-2-isopropyl malonate
(R)-4-(2-(bromomethyl)-3-methylbutyl)-1-methoxy-2-(3-methoxypropoxy)benzene
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1.1: sodium hydroxide; water / ethanol / 72 h / Reflux 1.2: pH 1 - 1.2 1.3: 35 h / 155 °C 2.1: (S)-1-phenyl-ethylamine / ethyl acetate / 4 h / 10 °C 2.2: pH 1 - 1.2 3.1: sodium bis(2-methoxyethoxy)aluminium dihydride / toluene / 2 h / 20 °C 3.2: 5 °C 4.1: triphenylphosphine; N-Bromosuccinimide / dichloromethane / 4 h / 5 - 10 °C View Scheme |
isopentanoyl chloride
(R)-4-(2-(bromomethyl)-3-methylbutyl)-1-methoxy-2-(3-methoxypropoxy)benzene
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1.1: sodium hydride / tetrahydrofuran / 0 - 5 °C / Inert atmosphere 2.1: lithium hexamethyldisilazane / tetrahydrofuran / 1.17 h / 70 °C / Inert atmosphere 2.2: 0 - 70 °C / Inert atmosphere 3.1: dihydrogen peroxide; lithium hydroxide monohydrate / tetrahydrofuran; water / 0 - 20 °C 4.1: sodium tetrahydroborate; boron trifluoride diethyl etherate / tetrahydrofuran / 5 h / 20 °C / Inert atmosphere 5.1: phosphorus tribromide / dichloromethane / 0 °C View Scheme |
(R)-4-(2-(bromomethyl)-3-methylbutyl)-1-methoxy-2-(3-methoxypropoxy)benzene
(R)-4-(2-(iodomethyl)-3-methylbutyl)-1-methoxy-2-(3-methoxypropoxy)benzene
Conditions | Yield |
---|---|
With sodium iodide In acetone at 20℃; for 20h; | 95% |
(2R)-2,5-dihydro-2-isopropyl-3,6-dimethoxypyrazine
(R)-4-(2-(bromomethyl)-3-methylbutyl)-1-methoxy-2-(3-methoxypropoxy)benzene
(2S,5R)-2,5-dihydro-3,6-dimethoxy-2-{(2S)-2-{[4-methoxy-3-(3-methoxypropoxy)phenyl]methyl}-3-methylbutyl}-5-(1-methylethyl)pyrazine
Conditions | Yield |
---|---|
Stage #1: (2R)-2,5-dihydro-2-isopropyl-3,6-dimethoxypyrazine With n-butyllithium In hexane at -75℃; for 0.5h; Stage #2: (R)-4-(2-(bromomethyl)-3-methylbutyl)-1-methoxy-2-(3-methoxypropoxy)benzene In tetrahydrofuran at -75 - -20℃; for 20h; | 91% |
Stage #1: (2R)-2,5-dihydro-2-isopropyl-3,6-dimethoxypyrazine With n-butyllithium In tetrahydrofuran at -75℃; Stage #2: (R)-4-(2-(bromomethyl)-3-methylbutyl)-1-methoxy-2-(3-methoxypropoxy)benzene In tetrahydrofuran at -75 - -18℃; | 90% |
(S)-2-isopropyl-3,6-dimethoxy-2,5-dihydropyrazine
(R)-4-(2-(bromomethyl)-3-methylbutyl)-1-methoxy-2-(3-methoxypropoxy)benzene
(2R,5S)-2,5-dihydro-3,6-dimethoxy-2-{(2R)-2-{[4-methoxy-3-(3-methoxypropoxy)phenyl]methyl}-3-methylbutyl}-5-(1-methylethyl)pyrazine
Conditions | Yield |
---|---|
Stage #1: (S)-2-isopropyl-3,6-dimethoxy-2,5-dihydropyrazine With n-butyllithium In hexane at -75℃; for 2h; Stage #2: (R)-4-(2-(bromomethyl)-3-methylbutyl)-1-methoxy-2-(3-methoxypropoxy)benzene In tetrahydrofuran at -20℃; for 16h; | 68% |
(2R)-3,6-diethoxy-2-isopropyl-2,5-dihydropyrazine
(R)-4-(2-(bromomethyl)-3-methylbutyl)-1-methoxy-2-(3-methoxypropoxy)benzene
(2R,5S)-3,6-diethoxy-2-isopropyl-5-((S)-2-(4-methoxy-3-(3-methoxypropoxy)benzyl)-3-methylbutyl)-2,5-dihydropyrazine
Conditions | Yield |
---|---|
With n-butyllithium | 68% |
Stage #1: (2R)-3,6-diethoxy-2-isopropyl-2,5-dihydropyrazine With n-butyllithium In tetrahydrofuran at -78℃; for 0.833333h; Stage #2: (R)-4-(2-(bromomethyl)-3-methylbutyl)-1-methoxy-2-(3-methoxypropoxy)benzene In tetrahydrofuran for 168h; |
(S)-2-isopropyl-3,6-dimethoxy-2,5-dihydropyrazine
(R)-4-(2-(bromomethyl)-3-methylbutyl)-1-methoxy-2-(3-methoxypropoxy)benzene
B
(2R,5S)-2,5-dihydro-3,6-dimethoxy-2-{(2S)-2-{[4-methoxy-3-(3-methoxypropoxy)phenyl]methyl}-3-methylbutyl}-5-(1-methylethyl)pyrazine
Conditions | Yield |
---|---|
Stage #1: (S)-2-isopropyl-3,6-dimethoxy-2,5-dihydropyrazine With n-butyllithium In hexane at -75℃; for 0.5h; Stage #2: (R)-4-(2-(bromomethyl)-3-methylbutyl)-1-methoxy-2-(3-methoxypropoxy)benzene In tetrahydrofuran at -75 - -20℃; for 50h; | A 26% B 28% |
(2R)-2,5-dihydro-2-isopropyl-3,6-dimethoxypyrazine
(R)-4-(2-(bromomethyl)-3-methylbutyl)-1-methoxy-2-(3-methoxypropoxy)benzene
Conditions | Yield |
---|---|
Stage #1: (2R)-2,5-dihydro-2-isopropyl-3,6-dimethoxypyrazine With n-butyllithium In hexane at -75℃; for 2h; Stage #2: (R)-4-(2-(bromomethyl)-3-methylbutyl)-1-methoxy-2-(3-methoxypropoxy)benzene In tetrahydrofuran at -20℃; for 16h; | A 20% B 22% |
3,6-Diethoxy-2,5-dihydropyridazin
(R)-4-(2-(bromomethyl)-3-methylbutyl)-1-methoxy-2-(3-methoxypropoxy)benzene
B
(2S)-3,6-diethoxy-2,5-dihydro-2-{(2S)-2-{[4-methoxy-3-(3-methoxypropoxy)phenyl]methyl}-3-methylbutyl}-pyrazine
Conditions | Yield |
---|---|
Stage #1: 3,6-Diethoxy-2,5-dihydropyridazin With n-butyllithium In tetrahydrofuran; hexane at -40℃; for 0.25h; Stage #2: (R)-4-(2-(bromomethyl)-3-methylbutyl)-1-methoxy-2-(3-methoxypropoxy)benzene In tetrahydrofuran at -20℃; for 16h; |
sodium cyanide
(R)-4-(2-(bromomethyl)-3-methylbutyl)-1-methoxy-2-(3-methoxypropoxy)benzene
(S)-3-[4-methoxy-3-(3-methoxy-propoxy)-benzyl]-4-methyl-pentanenitrile
Conditions | Yield |
---|---|
In 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone at 50℃; for 2h; | |
In 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone at 50℃; for 2h; |
(R)-4-(2-(bromomethyl)-3-methylbutyl)-1-methoxy-2-(3-methoxypropoxy)benzene
tert-butyl {(1S,3S)-1-((2S,4S)-4-isopropyl-5-oxotetrahydrofuran-2-yl)-3-[4-methoxy-3-(3-methoxypropoxy)benzyl]-4-methylpentyl}carbamate
Conditions | Yield |
---|---|
Multi-step reaction with 10 steps 1.1: n-BuLi / tetrahydrofuran / -75 °C 1.2: 90 percent / tetrahydrofuran / -75 - -18 °C 2.1: 99 percent / HCl / H2O; acetonitrile 3.1: 89 percent / pyridine / CH2Cl2 / 2 h / 20 °C 4.1: aq. NaOH / tetrahydrofuran; methanol / 3.5 h / 20 °C 5.1: 94 percent / EDCI / CH2Cl2 / 3.5 h / 0 °C 6.1: 67 percent / t-BuOH; SmI2 / tetrahydrofuran / 144 h / -78 °C 7.1: 85 mg / (S)-Alpine Hydride / tetrahydrofuran / 24 h / -78 °C 8.1: LiHMDS / tetrahydrofuran; hexane / 2 h / -78 °C 8.2: 91 percent / tetrahydrofuran; hexane / 2 h / -78 °C 9.1: PCl5 / CH2Cl2 / 2.5 h / 0 °C 9.2: 39 mg / H2 / Pd/C / ethanol / 48 h 10.1: 63 percent / Et3N / tetrahydrofuran / 18 h / 20 °C View Scheme | |
Multi-step reaction with 11 steps 1.1: n-BuLi / tetrahydrofuran / -75 °C 1.2: 90 percent / tetrahydrofuran / -75 - -18 °C 2.1: 99 percent / HCl / H2O; acetonitrile 3.1: 89 percent / pyridine / CH2Cl2 / 2 h / 20 °C 4.1: aq. NaOH / tetrahydrofuran; methanol / 3.5 h / 20 °C 5.1: 94 percent / EDCI / CH2Cl2 / 3.5 h / 0 °C 6.1: 67 percent / t-BuOH; SmI2 / tetrahydrofuran / 144 h / -78 °C 7.1: 85 mg / (S)-Alpine Hydride / tetrahydrofuran / 24 h / -78 °C 8.1: LiHMDS / tetrahydrofuran; hexane / 2 h / -78 °C 8.2: 91 percent / tetrahydrofuran; hexane / 2 h / -78 °C 9.1: PCl5 / CH2Cl2 / 2.5 h / 0 °C 9.2: 32 mg / 2-hydroxypyridine; Et3N / acetonitrile / 48 h / 80 °C 10.1: 94 percent / H2 / Pd/C / ethanol / 18 h 11.1: 63 percent / Et3N / tetrahydrofuran / 18 h / 20 °C View Scheme | |
Multi-step reaction with 8 steps 1: 68 percent / n-BuLi 2: HCl / acetonitrile 3: Et3N 4: NaBH4 / ethanol 5: 89 percent / DMSO; ClC(O)C(O)Cl; Et3N / CH2Cl2 6: Mg 7: 23 percent / H2 / Pd(OH)2/C 8: 38 percent / TPAP; NMMO View Scheme |
(R)-4-(2-(bromomethyl)-3-methylbutyl)-1-methoxy-2-(3-methoxypropoxy)benzene
Conditions | Yield |
---|---|
Multi-step reaction with 9 steps 1.1: n-BuLi / tetrahydrofuran / -75 °C 1.2: 90 percent / tetrahydrofuran / -75 - -18 °C 2.1: 99 percent / HCl / H2O; acetonitrile 3.1: 89 percent / pyridine / CH2Cl2 / 2 h / 20 °C 4.1: aq. NaOH / tetrahydrofuran; methanol / 3.5 h / 20 °C 5.1: 94 percent / EDCI / CH2Cl2 / 3.5 h / 0 °C 6.1: 67 percent / t-BuOH; SmI2 / tetrahydrofuran / 144 h / -78 °C 7.1: 85 mg / (S)-Alpine Hydride / tetrahydrofuran / 24 h / -78 °C 8.1: LiHMDS / tetrahydrofuran; hexane / 2 h / -78 °C 8.2: 91 percent / tetrahydrofuran; hexane / 2 h / -78 °C 9.1: PCl5 / CH2Cl2 / 2.5 h / 0 °C 9.2: 39 mg / H2 / Pd/C / ethanol / 48 h View Scheme | |
Multi-step reaction with 10 steps 1.1: n-BuLi / tetrahydrofuran / -75 °C 1.2: 90 percent / tetrahydrofuran / -75 - -18 °C 2.1: 99 percent / HCl / H2O; acetonitrile 3.1: 89 percent / pyridine / CH2Cl2 / 2 h / 20 °C 4.1: aq. NaOH / tetrahydrofuran; methanol / 3.5 h / 20 °C 5.1: 94 percent / EDCI / CH2Cl2 / 3.5 h / 0 °C 6.1: 67 percent / t-BuOH; SmI2 / tetrahydrofuran / 144 h / -78 °C 7.1: 85 mg / (S)-Alpine Hydride / tetrahydrofuran / 24 h / -78 °C 8.1: LiHMDS / tetrahydrofuran; hexane / 2 h / -78 °C 8.2: 91 percent / tetrahydrofuran; hexane / 2 h / -78 °C 9.1: PCl5 / CH2Cl2 / 2.5 h / 0 °C 9.2: 32 mg / 2-hydroxypyridine; Et3N / acetonitrile / 48 h / 80 °C 10.1: 94 percent / H2 / Pd/C / ethanol / 18 h View Scheme |
(R)-4-(2-(bromomethyl)-3-methylbutyl)-1-methoxy-2-(3-methoxypropoxy)benzene
methyl (2S,4S)-2-[[(phenylmethoxy)carbonyl]amino]-4-methoxy-3-(3-methoxypropoxy)-γ-(1-methylethyl)benzenepentanoate
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: n-BuLi / tetrahydrofuran / -75 °C 1.2: 90 percent / tetrahydrofuran / -75 - -18 °C 2.1: 99 percent / HCl / H2O; acetonitrile 3.1: 89 percent / pyridine / CH2Cl2 / 2 h / 20 °C View Scheme |
(R)-4-(2-(bromomethyl)-3-methylbutyl)-1-methoxy-2-(3-methoxypropoxy)benzene
Conditions | Yield |
---|---|
Multi-step reaction with 10 steps 1.1: n-BuLi / tetrahydrofuran / -75 °C 1.2: 90 percent / tetrahydrofuran / -75 - -18 °C 2.1: 99 percent / HCl / H2O; acetonitrile 3.1: 89 percent / pyridine / CH2Cl2 / 2 h / 20 °C 4.1: aq. NaOH / tetrahydrofuran; methanol / 3.5 h / 20 °C 5.1: 94 percent / EDCI / CH2Cl2 / 3.5 h / 0 °C 6.1: 67 percent / t-BuOH; SmI2 / tetrahydrofuran / 144 h / -78 °C 7.1: 85 mg / (S)-Alpine Hydride / tetrahydrofuran / 24 h / -78 °C 8.1: LiHMDS / tetrahydrofuran; hexane / 2 h / -78 °C 8.2: 91 percent / tetrahydrofuran; hexane / 2 h / -78 °C 9.1: PCl5 / CH2Cl2 / 2.5 h / 0 °C 9.2: 39 mg / H2 / Pd/C / ethanol / 48 h 10.1: ethanol / 1.5 h / 0 °C View Scheme | |
Multi-step reaction with 11 steps 1.1: n-BuLi / tetrahydrofuran / -75 °C 1.2: 90 percent / tetrahydrofuran / -75 - -18 °C 2.1: 99 percent / HCl / H2O; acetonitrile 3.1: 89 percent / pyridine / CH2Cl2 / 2 h / 20 °C 4.1: aq. NaOH / tetrahydrofuran; methanol / 3.5 h / 20 °C 5.1: 94 percent / EDCI / CH2Cl2 / 3.5 h / 0 °C 6.1: 67 percent / t-BuOH; SmI2 / tetrahydrofuran / 144 h / -78 °C 7.1: 85 mg / (S)-Alpine Hydride / tetrahydrofuran / 24 h / -78 °C 8.1: LiHMDS / tetrahydrofuran; hexane / 2 h / -78 °C 8.2: 91 percent / tetrahydrofuran; hexane / 2 h / -78 °C 9.1: PCl5 / CH2Cl2 / 2.5 h / 0 °C 9.2: 32 mg / 2-hydroxypyridine; Et3N / acetonitrile / 48 h / 80 °C 10.1: 94 percent / H2 / Pd/C / ethanol / 18 h 11.1: ethanol / 1.5 h / 0 °C View Scheme |
(R)-4-(2-(bromomethyl)-3-methylbutyl)-1-methoxy-2-(3-methoxypropoxy)benzene
(2S,4S)-2-[[(phenylmethoxy)carbonyl]amino]-4-methoxy-3-(3-methoxypropoxy)-γ-(1-methylethyl)benzenepentanoic acid
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1.1: n-BuLi / tetrahydrofuran / -75 °C 1.2: 90 percent / tetrahydrofuran / -75 - -18 °C 2.1: 99 percent / HCl / H2O; acetonitrile 3.1: 89 percent / pyridine / CH2Cl2 / 2 h / 20 °C 4.1: aq. NaOH / tetrahydrofuran; methanol / 3.5 h / 20 °C View Scheme |
(R)-4-(2-(bromomethyl)-3-methylbutyl)-1-methoxy-2-(3-methoxypropoxy)benzene
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 95 percent / NaI / acetone / 20 h / 20 °C 2: LiHMDS; LiCl / tetrahydrofuran / 0 - 20 °C View Scheme |
(R)-4-(2-(bromomethyl)-3-methylbutyl)-1-methoxy-2-(3-methoxypropoxy)benzene
Conditions | Yield |
---|---|
Multi-step reaction with 11 steps 1.1: n-BuLi / tetrahydrofuran / -75 °C 1.2: 90 percent / tetrahydrofuran / -75 - -18 °C 2.1: 99 percent / HCl / H2O; acetonitrile 3.1: 89 percent / pyridine / CH2Cl2 / 2 h / 20 °C 4.1: aq. NaOH / tetrahydrofuran; methanol / 3.5 h / 20 °C 5.1: 94 percent / EDCI / CH2Cl2 / 3.5 h / 0 °C 6.1: 67 percent / t-BuOH; SmI2 / tetrahydrofuran / 144 h / -78 °C 7.1: 85 mg / (S)-Alpine Hydride / tetrahydrofuran / 24 h / -78 °C 8.1: LiHMDS / tetrahydrofuran; hexane / 2 h / -78 °C 8.2: 91 percent / tetrahydrofuran; hexane / 2 h / -78 °C 9.1: PCl5 / CH2Cl2 / 2.5 h / 0 °C 9.2: 39 mg / H2 / Pd/C / ethanol / 48 h 10.1: ethanol / 1.5 h / 0 °C 11.1: 6 mg / NaBH4 / ethanol / 0.67 h / 20 °C View Scheme | |
Multi-step reaction with 12 steps 1.1: n-BuLi / tetrahydrofuran / -75 °C 1.2: 90 percent / tetrahydrofuran / -75 - -18 °C 2.1: 99 percent / HCl / H2O; acetonitrile 3.1: 89 percent / pyridine / CH2Cl2 / 2 h / 20 °C 4.1: aq. NaOH / tetrahydrofuran; methanol / 3.5 h / 20 °C 5.1: 94 percent / EDCI / CH2Cl2 / 3.5 h / 0 °C 6.1: 67 percent / t-BuOH; SmI2 / tetrahydrofuran / 144 h / -78 °C 7.1: 85 mg / (S)-Alpine Hydride / tetrahydrofuran / 24 h / -78 °C 8.1: LiHMDS / tetrahydrofuran; hexane / 2 h / -78 °C 8.2: 91 percent / tetrahydrofuran; hexane / 2 h / -78 °C 9.1: PCl5 / CH2Cl2 / 2.5 h / 0 °C 9.2: 32 mg / 2-hydroxypyridine; Et3N / acetonitrile / 48 h / 80 °C 10.1: 94 percent / H2 / Pd/C / ethanol / 18 h 11.1: ethanol / 1.5 h / 0 °C 12.1: 6 mg / NaBH4 / ethanol / 0.67 h / 20 °C View Scheme |
(R)-4-(2-(bromomethyl)-3-methylbutyl)-1-methoxy-2-(3-methoxypropoxy)benzene
(3S,5S)-dihydro-5-[(1S,3S)-3-[[4-methoxy-3-(3-methoxypropoxy)phenyl]methyl]-4-methyl-1-[(phenylmethyl)amino]pentyl]-3-(1-methylethyl)-2(3H)-furanone
Conditions | Yield |
---|---|
Multi-step reaction with 11 steps 1.1: n-BuLi / tetrahydrofuran / -75 °C 1.2: 90 percent / tetrahydrofuran / -75 - -18 °C 2.1: 99 percent / HCl / H2O; acetonitrile 3.1: 89 percent / pyridine / CH2Cl2 / 2 h / 20 °C 4.1: aq. NaOH / tetrahydrofuran; methanol / 3.5 h / 20 °C 5.1: 94 percent / EDCI / CH2Cl2 / 3.5 h / 0 °C 6.1: 67 percent / t-BuOH; SmI2 / tetrahydrofuran / 144 h / -78 °C 7.1: 85 mg / (S)-Alpine Hydride / tetrahydrofuran / 24 h / -78 °C 8.1: LiHMDS / tetrahydrofuran; hexane / 2 h / -78 °C 8.2: 91 percent / tetrahydrofuran; hexane / 2 h / -78 °C 9.1: PCl5 / CH2Cl2 / 2.5 h / 0 °C 9.2: 39 mg / H2 / Pd/C / ethanol / 48 h 10.1: ethanol / 1.5 h / 0 °C 11.1: 24 mg / NaBH4 / ethanol / 0.67 h / 20 °C View Scheme | |
Multi-step reaction with 12 steps 1.1: n-BuLi / tetrahydrofuran / -75 °C 1.2: 90 percent / tetrahydrofuran / -75 - -18 °C 2.1: 99 percent / HCl / H2O; acetonitrile 3.1: 89 percent / pyridine / CH2Cl2 / 2 h / 20 °C 4.1: aq. NaOH / tetrahydrofuran; methanol / 3.5 h / 20 °C 5.1: 94 percent / EDCI / CH2Cl2 / 3.5 h / 0 °C 6.1: 67 percent / t-BuOH; SmI2 / tetrahydrofuran / 144 h / -78 °C 7.1: 85 mg / (S)-Alpine Hydride / tetrahydrofuran / 24 h / -78 °C 8.1: LiHMDS / tetrahydrofuran; hexane / 2 h / -78 °C 8.2: 91 percent / tetrahydrofuran; hexane / 2 h / -78 °C 9.1: PCl5 / CH2Cl2 / 2.5 h / 0 °C 9.2: 32 mg / 2-hydroxypyridine; Et3N / acetonitrile / 48 h / 80 °C 10.1: 94 percent / H2 / Pd/C / ethanol / 18 h 11.1: ethanol / 1.5 h / 0 °C 12.1: 24 mg / NaBH4 / ethanol / 0.67 h / 20 °C View Scheme |
(R)-4-(2-(bromomethyl)-3-methylbutyl)-1-methoxy-2-(3-methoxypropoxy)benzene
1,1-dimethylethyl [(1S,3S)-3-[[4-methoxy-3-(3-methoxypropoxy)phenyl]methyl]-4-methyl-1-[(2S,4R)-tetrahydro-4-(1-methylethyl)-5-oxo-2-furanyl]pentyl]carbamate
Conditions | Yield |
---|---|
Multi-step reaction with 10 steps 1.1: n-BuLi / tetrahydrofuran / -75 °C 1.2: 90 percent / tetrahydrofuran / -75 - -18 °C 2.1: 99 percent / HCl / H2O; acetonitrile 3.1: 89 percent / pyridine / CH2Cl2 / 2 h / 20 °C 4.1: aq. NaOH / tetrahydrofuran; methanol / 3.5 h / 20 °C 5.1: 94 percent / EDCI / CH2Cl2 / 3.5 h / 0 °C 6.1: 67 percent / t-BuOH; SmI2 / tetrahydrofuran / 144 h / -78 °C 7.1: 85 mg / (S)-Alpine Hydride / tetrahydrofuran / 24 h / -78 °C 8.1: LiHMDS / tetrahydrofuran; hexane / 2 h / -78 °C 8.2: 91 percent / tetrahydrofuran; hexane / 2 h / -78 °C 9.1: PCl5 / CH2Cl2 / 2.5 h / 0 °C 9.2: 39 mg / H2 / Pd/C / ethanol / 48 h 10.1: Et3N / tetrahydrofuran / 18 h / 20 °C View Scheme | |
Multi-step reaction with 10 steps 1.1: n-BuLi / tetrahydrofuran / -75 °C 1.2: 90 percent / tetrahydrofuran / -75 - -18 °C 2.1: 99 percent / HCl / H2O; acetonitrile 3.1: 89 percent / pyridine / CH2Cl2 / 2 h / 20 °C 4.1: aq. NaOH / tetrahydrofuran; methanol / 3.5 h / 20 °C 5.1: 94 percent / EDCI / CH2Cl2 / 3.5 h / 0 °C 6.1: 67 percent / t-BuOH; SmI2 / tetrahydrofuran / 144 h / -78 °C 7.1: 85 mg / (S)-Alpine Hydride / tetrahydrofuran / 24 h / -78 °C 8.1: LiHMDS / tetrahydrofuran; hexane / 2 h / -78 °C 8.2: 91 percent / tetrahydrofuran; hexane / 2 h / -78 °C 9.1: PCl5 / CH2Cl2 / 2.5 h / 0 °C 9.2: 39 mg / H2 / Pd/C / ethanol / 48 h 10.1: 81 percent / Et3N / tetrahydrofuran / 18 h / 20 °C View Scheme | |
Multi-step reaction with 11 steps 1.1: n-BuLi / tetrahydrofuran / -75 °C 1.2: 90 percent / tetrahydrofuran / -75 - -18 °C 2.1: 99 percent / HCl / H2O; acetonitrile 3.1: 89 percent / pyridine / CH2Cl2 / 2 h / 20 °C 4.1: aq. NaOH / tetrahydrofuran; methanol / 3.5 h / 20 °C 5.1: 94 percent / EDCI / CH2Cl2 / 3.5 h / 0 °C 6.1: 67 percent / t-BuOH; SmI2 / tetrahydrofuran / 144 h / -78 °C 7.1: 85 mg / (S)-Alpine Hydride / tetrahydrofuran / 24 h / -78 °C 8.1: LiHMDS / tetrahydrofuran; hexane / 2 h / -78 °C 8.2: 91 percent / tetrahydrofuran; hexane / 2 h / -78 °C 9.1: PCl5 / CH2Cl2 / 2.5 h / 0 °C 9.2: 32 mg / 2-hydroxypyridine; Et3N / acetonitrile / 48 h / 80 °C 10.1: 94 percent / H2 / Pd/C / ethanol / 18 h 11.1: Et3N / tetrahydrofuran / 18 h / 20 °C View Scheme | |
Multi-step reaction with 11 steps 1.1: n-BuLi / tetrahydrofuran / -75 °C 1.2: 90 percent / tetrahydrofuran / -75 - -18 °C 2.1: 99 percent / HCl / H2O; acetonitrile 3.1: 89 percent / pyridine / CH2Cl2 / 2 h / 20 °C 4.1: aq. NaOH / tetrahydrofuran; methanol / 3.5 h / 20 °C 5.1: 94 percent / EDCI / CH2Cl2 / 3.5 h / 0 °C 6.1: 67 percent / t-BuOH; SmI2 / tetrahydrofuran / 144 h / -78 °C 7.1: 85 mg / (S)-Alpine Hydride / tetrahydrofuran / 24 h / -78 °C 8.1: LiHMDS / tetrahydrofuran; hexane / 2 h / -78 °C 8.2: 91 percent / tetrahydrofuran; hexane / 2 h / -78 °C 9.1: PCl5 / CH2Cl2 / 2.5 h / 0 °C 9.2: 32 mg / 2-hydroxypyridine; Et3N / acetonitrile / 48 h / 80 °C 10.1: 94 percent / H2 / Pd/C / ethanol / 18 h 11.1: 81 percent / Et3N / tetrahydrofuran / 18 h / 20 °C View Scheme |
(R)-4-(2-(bromomethyl)-3-methylbutyl)-1-methoxy-2-(3-methoxypropoxy)benzene
phenylmethyl [(1S,3S)-3-[[4-methoxy-3-(3-methoxypropoxy)phenyl]methyl]-4-methyl-1-[(2S)-tetrahydro-5-oxo-2-furanyl]pentyl]carbamate
Conditions | Yield |
---|---|
Multi-step reaction with 7 steps 1.1: n-BuLi / tetrahydrofuran / -75 °C 1.2: 90 percent / tetrahydrofuran / -75 - -18 °C 2.1: 99 percent / HCl / H2O; acetonitrile 3.1: 89 percent / pyridine / CH2Cl2 / 2 h / 20 °C 4.1: aq. NaOH / tetrahydrofuran; methanol / 3.5 h / 20 °C 5.1: 94 percent / EDCI / CH2Cl2 / 3.5 h / 0 °C 6.1: 67 percent / t-BuOH; SmI2 / tetrahydrofuran / 144 h / -78 °C 7.1: 85 mg / (S)-Alpine Hydride / tetrahydrofuran / 24 h / -78 °C View Scheme |
(R)-4-(2-(bromomethyl)-3-methylbutyl)-1-methoxy-2-(3-methoxypropoxy)benzene
Conditions | Yield |
---|---|
Multi-step reaction with 7 steps 1.1: n-BuLi / tetrahydrofuran / -75 °C 1.2: 90 percent / tetrahydrofuran / -75 - -18 °C 2.1: 99 percent / HCl / H2O; acetonitrile 3.1: 89 percent / pyridine / CH2Cl2 / 2 h / 20 °C 4.1: aq. NaOH / tetrahydrofuran; methanol / 3.5 h / 20 °C 5.1: 94 percent / EDCI / CH2Cl2 / 3.5 h / 0 °C 6.1: 67 percent / t-BuOH; SmI2 / tetrahydrofuran / 144 h / -78 °C 7.1: 21 mg / (S)-Alpine Hydride / tetrahydrofuran / 24 h / -78 °C View Scheme |
(R)-4-(2-(bromomethyl)-3-methylbutyl)-1-methoxy-2-(3-methoxypropoxy)benzene
(5S,7S)-5-Benzyloxycarbonylamino-7-[4-methoxy-3-(3-methoxy-propoxy)-benzyl]-8-methyl-4-oxo-nonanoic acid methyl ester
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1.1: n-BuLi / tetrahydrofuran / -75 °C 1.2: 90 percent / tetrahydrofuran / -75 - -18 °C 2.1: 99 percent / HCl / H2O; acetonitrile 3.1: 89 percent / pyridine / CH2Cl2 / 2 h / 20 °C 4.1: aq. NaOH / tetrahydrofuran; methanol / 3.5 h / 20 °C 5.1: 94 percent / EDCI / CH2Cl2 / 3.5 h / 0 °C 6.1: 67 percent / t-BuOH; SmI2 / tetrahydrofuran / 144 h / -78 °C View Scheme |
(R)-4-(2-(bromomethyl)-3-methylbutyl)-1-methoxy-2-(3-methoxypropoxy)benzene
pyridin-4-yl (2S,4S)-2-[[(phenylmethoxy)carbonyl]amino]-4-methoxy-3-(3-methoxypropoxy)-γ-(1-methylethyl)benzenepentanethioate
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1.1: n-BuLi / tetrahydrofuran / -75 °C 1.2: 90 percent / tetrahydrofuran / -75 - -18 °C 2.1: 99 percent / HCl / H2O; acetonitrile 3.1: 89 percent / pyridine / CH2Cl2 / 2 h / 20 °C 4.1: aq. NaOH / tetrahydrofuran; methanol / 3.5 h / 20 °C 5.1: 94 percent / EDCI / CH2Cl2 / 3.5 h / 0 °C View Scheme |
(R)-4-(2-(bromomethyl)-3-methylbutyl)-1-methoxy-2-(3-methoxypropoxy)benzene
{(1S,3S)-1-((S)-4-Isopropylidene-5-oxo-tetrahydro-furan-2-yl)-3-[4-methoxy-3-(3-methoxy-propoxy)-benzyl]-4-methyl-pentyl}-carbamic acid benzyl ester
Conditions | Yield |
---|---|
Multi-step reaction with 9 steps 1.1: n-BuLi / tetrahydrofuran / -75 °C 1.2: 90 percent / tetrahydrofuran / -75 - -18 °C 2.1: 99 percent / HCl / H2O; acetonitrile 3.1: 89 percent / pyridine / CH2Cl2 / 2 h / 20 °C 4.1: aq. NaOH / tetrahydrofuran; methanol / 3.5 h / 20 °C 5.1: 94 percent / EDCI / CH2Cl2 / 3.5 h / 0 °C 6.1: 67 percent / t-BuOH; SmI2 / tetrahydrofuran / 144 h / -78 °C 7.1: 85 mg / (S)-Alpine Hydride / tetrahydrofuran / 24 h / -78 °C 8.1: LiHMDS / tetrahydrofuran; hexane / 2 h / -78 °C 8.2: 91 percent / tetrahydrofuran; hexane / 2 h / -78 °C 9.1: PCl5 / CH2Cl2 / 2.5 h / 0 °C 9.2: 32 mg / 2-hydroxypyridine; Et3N / acetonitrile / 48 h / 80 °C View Scheme |
(R)-4-(2-(bromomethyl)-3-methylbutyl)-1-methoxy-2-(3-methoxypropoxy)benzene
Conditions | Yield |
---|---|
Multi-step reaction with 8 steps 1.1: n-BuLi / tetrahydrofuran / -75 °C 1.2: 90 percent / tetrahydrofuran / -75 - -18 °C 2.1: 99 percent / HCl / H2O; acetonitrile 3.1: 89 percent / pyridine / CH2Cl2 / 2 h / 20 °C 4.1: aq. NaOH / tetrahydrofuran; methanol / 3.5 h / 20 °C 5.1: 94 percent / EDCI / CH2Cl2 / 3.5 h / 0 °C 6.1: 67 percent / t-BuOH; SmI2 / tetrahydrofuran / 144 h / -78 °C 7.1: 85 mg / (S)-Alpine Hydride / tetrahydrofuran / 24 h / -78 °C 8.1: LiHMDS / tetrahydrofuran; hexane / 2 h / -78 °C 8.2: 91 percent / tetrahydrofuran; hexane / 2 h / -78 °C View Scheme |
(R)-4-(2-(bromomethyl)-3-methylbutyl)-1-methoxy-2-(3-methoxypropoxy)benzene
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1.1: n-BuLi / tetrahydrofuran / -75 °C 1.2: 90 percent / tetrahydrofuran / -75 - -18 °C 2.1: 99 percent / HCl / H2O; acetonitrile 3.1: 89 percent / pyridine / CH2Cl2 / 2 h / 20 °C 4.1: aq. NaOH / tetrahydrofuran; methanol / 3.5 h / 20 °C 5.1: 94 percent / EDCI / CH2Cl2 / 3.5 h / 0 °C 6.1: 60 percent / t-BuOH; SmI2 / tetrahydrofuran / 72 h / -78 °C View Scheme |
(R)-4-(2-(bromomethyl)-3-methylbutyl)-1-methoxy-2-(3-methoxypropoxy)benzene
Conditions | Yield |
---|---|
Multi-step reaction with 11 steps 1.1: n-BuLi / tetrahydrofuran / -75 °C 1.2: 90 percent / tetrahydrofuran / -75 - -18 °C 2.1: 99 percent / HCl / H2O; acetonitrile 3.1: 89 percent / pyridine / CH2Cl2 / 2 h / 20 °C 4.1: aq. NaOH / tetrahydrofuran; methanol / 3.5 h / 20 °C 5.1: 94 percent / EDCI / CH2Cl2 / 3.5 h / 0 °C 6.1: 67 percent / t-BuOH; SmI2 / tetrahydrofuran / 144 h / -78 °C 7.1: 85 mg / (S)-Alpine Hydride / tetrahydrofuran / 24 h / -78 °C 8.1: LiHMDS / tetrahydrofuran; hexane / 2 h / -78 °C 8.2: 91 percent / tetrahydrofuran; hexane / 2 h / -78 °C 9.1: PCl5 / CH2Cl2 / 2.5 h / 0 °C 9.2: 39 mg / H2 / Pd/C / ethanol / 48 h 10.1: Et3N / tetrahydrofuran / 18 h / 20 °C 11.1: 48 percent / trimethylaluminum / CH2Cl2; toluene / 48 h / 20 °C View Scheme | |
Multi-step reaction with 11 steps 1.1: n-BuLi / tetrahydrofuran / -75 °C 1.2: 90 percent / tetrahydrofuran / -75 - -18 °C 2.1: 99 percent / HCl / H2O; acetonitrile 3.1: 89 percent / pyridine / CH2Cl2 / 2 h / 20 °C 4.1: aq. NaOH / tetrahydrofuran; methanol / 3.5 h / 20 °C 5.1: 94 percent / EDCI / CH2Cl2 / 3.5 h / 0 °C 6.1: 67 percent / t-BuOH; SmI2 / tetrahydrofuran / 144 h / -78 °C 7.1: 85 mg / (S)-Alpine Hydride / tetrahydrofuran / 24 h / -78 °C 8.1: LiHMDS / tetrahydrofuran; hexane / 2 h / -78 °C 8.2: 91 percent / tetrahydrofuran; hexane / 2 h / -78 °C 9.1: PCl5 / CH2Cl2 / 2.5 h / 0 °C 9.2: 39 mg / H2 / Pd/C / ethanol / 48 h 10.1: 81 percent / Et3N / tetrahydrofuran / 18 h / 20 °C 11.1: 48 percent / trimethylaluminum / CH2Cl2; toluene / 48 h / 20 °C View Scheme | |
Multi-step reaction with 12 steps 1.1: n-BuLi / tetrahydrofuran / -75 °C 1.2: 90 percent / tetrahydrofuran / -75 - -18 °C 2.1: 99 percent / HCl / H2O; acetonitrile 3.1: 89 percent / pyridine / CH2Cl2 / 2 h / 20 °C 4.1: aq. NaOH / tetrahydrofuran; methanol / 3.5 h / 20 °C 5.1: 94 percent / EDCI / CH2Cl2 / 3.5 h / 0 °C 6.1: 67 percent / t-BuOH; SmI2 / tetrahydrofuran / 144 h / -78 °C 7.1: 85 mg / (S)-Alpine Hydride / tetrahydrofuran / 24 h / -78 °C 8.1: LiHMDS / tetrahydrofuran; hexane / 2 h / -78 °C 8.2: 91 percent / tetrahydrofuran; hexane / 2 h / -78 °C 9.1: PCl5 / CH2Cl2 / 2.5 h / 0 °C 9.2: 32 mg / 2-hydroxypyridine; Et3N / acetonitrile / 48 h / 80 °C 10.1: 94 percent / H2 / Pd/C / ethanol / 18 h 11.1: Et3N / tetrahydrofuran / 18 h / 20 °C 12.1: 48 percent / trimethylaluminum / CH2Cl2; toluene / 48 h / 20 °C View Scheme | |
Multi-step reaction with 12 steps 1.1: n-BuLi / tetrahydrofuran / -75 °C 1.2: 90 percent / tetrahydrofuran / -75 - -18 °C 2.1: 99 percent / HCl / H2O; acetonitrile 3.1: 89 percent / pyridine / CH2Cl2 / 2 h / 20 °C 4.1: aq. NaOH / tetrahydrofuran; methanol / 3.5 h / 20 °C 5.1: 94 percent / EDCI / CH2Cl2 / 3.5 h / 0 °C 6.1: 67 percent / t-BuOH; SmI2 / tetrahydrofuran / 144 h / -78 °C 7.1: 85 mg / (S)-Alpine Hydride / tetrahydrofuran / 24 h / -78 °C 8.1: LiHMDS / tetrahydrofuran; hexane / 2 h / -78 °C 8.2: 91 percent / tetrahydrofuran; hexane / 2 h / -78 °C 9.1: PCl5 / CH2Cl2 / 2.5 h / 0 °C 9.2: 32 mg / 2-hydroxypyridine; Et3N / acetonitrile / 48 h / 80 °C 10.1: 94 percent / H2 / Pd/C / ethanol / 18 h 11.1: 81 percent / Et3N / tetrahydrofuran / 18 h / 20 °C 12.1: 48 percent / trimethylaluminum / CH2Cl2; toluene / 48 h / 20 °C View Scheme |
(R)-4-(2-(bromomethyl)-3-methylbutyl)-1-methoxy-2-(3-methoxypropoxy)benzene
(1S,2S,4S,2'S)-(4-butylcarbamoyl-2-hydroxy-1-{2'-[4-methoxy-3-(3-methoxypropoxy)benzyl]-3-methylbutyl}-5-methylhexyl)carbamic acid tert-butyl ester
Conditions | Yield |
---|---|
Multi-step reaction with 11 steps 1.1: n-BuLi / tetrahydrofuran / -75 °C 1.2: 90 percent / tetrahydrofuran / -75 - -18 °C 2.1: 99 percent / HCl / H2O; acetonitrile 3.1: 89 percent / pyridine / CH2Cl2 / 2 h / 20 °C 4.1: aq. NaOH / tetrahydrofuran; methanol / 3.5 h / 20 °C 5.1: 94 percent / EDCI / CH2Cl2 / 3.5 h / 0 °C 6.1: 67 percent / t-BuOH; SmI2 / tetrahydrofuran / 144 h / -78 °C 7.1: 85 mg / (S)-Alpine Hydride / tetrahydrofuran / 24 h / -78 °C 8.1: LiHMDS / tetrahydrofuran; hexane / 2 h / -78 °C 8.2: 91 percent / tetrahydrofuran; hexane / 2 h / -78 °C 9.1: PCl5 / CH2Cl2 / 2.5 h / 0 °C 9.2: 39 mg / H2 / Pd/C / ethanol / 48 h 10.1: 63 percent / Et3N / tetrahydrofuran / 18 h / 20 °C 11.1: 58 percent / trimethylaluminum / CH2Cl2; toluene / 20 h / 20 °C View Scheme | |
Multi-step reaction with 12 steps 1.1: n-BuLi / tetrahydrofuran / -75 °C 1.2: 90 percent / tetrahydrofuran / -75 - -18 °C 2.1: 99 percent / HCl / H2O; acetonitrile 3.1: 89 percent / pyridine / CH2Cl2 / 2 h / 20 °C 4.1: aq. NaOH / tetrahydrofuran; methanol / 3.5 h / 20 °C 5.1: 94 percent / EDCI / CH2Cl2 / 3.5 h / 0 °C 6.1: 67 percent / t-BuOH; SmI2 / tetrahydrofuran / 144 h / -78 °C 7.1: 85 mg / (S)-Alpine Hydride / tetrahydrofuran / 24 h / -78 °C 8.1: LiHMDS / tetrahydrofuran; hexane / 2 h / -78 °C 8.2: 91 percent / tetrahydrofuran; hexane / 2 h / -78 °C 9.1: PCl5 / CH2Cl2 / 2.5 h / 0 °C 9.2: 32 mg / 2-hydroxypyridine; Et3N / acetonitrile / 48 h / 80 °C 10.1: 94 percent / H2 / Pd/C / ethanol / 18 h 11.1: 63 percent / Et3N / tetrahydrofuran / 18 h / 20 °C 12.1: 58 percent / trimethylaluminum / CH2Cl2; toluene / 20 h / 20 °C View Scheme |
(R)-4-(2-(bromomethyl)-3-methylbutyl)-1-methoxy-2-(3-methoxypropoxy)benzene
methyl (2S,4S)-2-amino-4-[4-methoxy-3-(3-methoxypropoxy)benzyl]-5-methylhexanoate
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: n-BuLi / tetrahydrofuran / -75 °C 1.2: 90 percent / tetrahydrofuran / -75 - -18 °C 2.1: 99 percent / HCl / H2O; acetonitrile View Scheme | |
Multi-step reaction with 2 steps 1.1: BuLi / hexane / 0.5 h / -75 °C 1.2: 91 percent / tetrahydrofuran / 20 h / -75 - -20 °C 2.1: 90 percent / 1N HCl / acetonitrile / 1.5 h / 20 °C View Scheme |
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