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inquiryBenzene, 4-[(2R)-2-(chloromethyl)-3-methylbutyl]-1-methoxy-2-(3-methoxypropoxy)- Basic information Product Name: Benzene, 4-[(2R)-2-(chloromethyl)-3-methylbutyl]-1-methoxy-2-(3-methoxypropoxy)
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inquiryBenzene, 4-[(2R)-2-(chloromethyl)-3-methylbutyl]-1-methoxy-2-(3-methoxypropoxy)- CAS:324763-39-5 Qingdao Belugas Import and Export Co., Ltd. is a scientific and technological company integrating research and development, production and trade of che
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inquiryHello, dear friend! I'm Hansen and Allen from China. Welcome to my lookchem mall! The following is a brief introduction of our company's products and services. If you are interested in our products, please contact us by emai
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inquiryHenan Wentao Chemical Product Co.,Ltd is Located in Zhengzhou High-tech Development Zone with import and export license, We passed ISO 9001:2008 as well, Henan Wentao has developed more than 1000 compounds, which are widely used in the fields of prod
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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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inquiryName 4-[(2R)-2-(Chloromethyl)-3-methylbutyl]-1-methoxy-2-(3-methoxypropoxy)benzene Synonyms Aliskiren inter-1 Molecular Structure
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inquiryHangzhou KeyingChem Co., Ltd. exported this product to many countries and regions at best price. If you are looking for the material’s manufacturer or supplier in China, KeyingChem is your best choice. Pls contact with us freely for getting det
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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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inquiryHANGZHOU THINK CHEMICAL CO., LTD. (THINKCHEM) is an integrative corporation of trade, research and contract manufacture. With about ten years of business experiences on the marketing & distribution, thinkchem specializes in exp
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inquiryProduct Name: Benzene, 4-[(2R)-2-(chloromethyl)-3-methylbutyl]-1-methoxy-2-(3-methoxypropoxy)- Synonyms: Benzene, 4-[(2R)-2-(chloromethyl)-3-methylbu…Appearance:Solid powder Storage:Sealed,light and oxygen resistant Package:aluminum foil bag,carton
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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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inquiryhigh qualityAppearance:white crystalline powder Storage:Sealed, dry, microtherm , avoid light and smell. Package:According to the demand of customer Application:Organic synthesis Transportation:by air or by sea
Our clients, like BASF,CHEMO,Brenntag,ASR,Evonik,Merck and etc.Appearance:COA Storage:in stock Application:MSDS/TDS
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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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inquiryAnsciep Chemical is a professional enterprise manufacturing and distributing fine chemicals and speciality chemicals. We have been dedicated to heterocycle compounds and phenyl rings for tens of years. This is our mature product for export. Our quali
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inquiry4-[(2R)-2-(Chloromethyl)-3-methylbutyl]-1-methoxy-2-(3-methoxypropoxy)benzene cas 324763-39-5Appearance: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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inquiryKnown for its best quality and competitve price, this chemicals we offered is widely appreciated by our customers. Prompt reaction, good quality and best service make us reliable and outstanding in this industry.Appearance:White to slightly yellow cr
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inquiry(R)-2-[4-methoxy-3-(3-methoxypropoxy)benzyl]-3-methylbutanol
(R)-2-[4-methoxy-3-(3-methoxypropoxyl)]phenylmethyl-3-methyl-1-chlorobutane
Conditions | Yield |
---|---|
With tetrachloromethane; TOP at 20℃; for 16h; trioctylphosphine was added at 10 °ree;C; | 82% |
With pyridine; thionyl chloride | 70% |
With N,N-dimethyl-formamide; trichlorophosphate In toluene at 80℃; |
2-(3-(3-methoxypropoxy)-4-methoxybenzyl)-3-methylbutanol
(R)-2-[4-methoxy-3-(3-methoxypropoxyl)]phenylmethyl-3-methyl-1-chlorobutane
Conditions | Yield |
---|---|
With thionyl chloride; N,N-dimethyl-formamide In toluene at 90℃; for 2h; Product distribution / selectivity; | 64% |
4-methoxy-3-(3-methoxypropoxy)benzaldehyde
(R)-2-[4-methoxy-3-(3-methoxypropoxyl)]phenylmethyl-3-methyl-1-chlorobutane
Conditions | Yield |
---|---|
Multi-step reaction with 7 steps 1.1: 82 percent 2.1: H2 / Pd/C / ethyl acetate / 20 °C 3.1: (COCl)2 / dimethylformamide / 20 °C 4.1: NaOH / toluene / 20 °C 5.1: LDA; LiCl / tetrahydrofuran / 0 °C 5.2: tetrahydrofuran / 20 °C / Heating 6.1: 66 percent / BH3*NH3; n-BuLi / tetrahydrofuran / 20 °C 7.1: POCl3; DMF / toluene / 80 °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: N-chloro-succinimide; triphenylphosphine / 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: N-chloro-succinimide; triphenylphosphine / dichloromethane / 5.5 h / -40 - 30 °C View Scheme |
(R)-2-[4-methoxy-3-(3-methoxypropoxyl)]phenylmethyl-3-methyl-1-chlorobutane
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1.1: (COCl)2 / dimethylformamide / 20 °C 2.1: NaOH / toluene / 20 °C 3.1: LDA; LiCl / tetrahydrofuran / 0 °C 3.2: tetrahydrofuran / 20 °C / Heating 4.1: 66 percent / BH3*NH3; n-BuLi / tetrahydrofuran / 20 °C 5.1: POCl3; DMF / toluene / 80 °C View Scheme |
(R)-2-[4-methoxy-3-(3-methoxypropoxyl)]phenylmethyl-3-methyl-1-chlorobutane
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1.1: NaOH / toluene / 20 °C 2.1: LDA; LiCl / tetrahydrofuran / 0 °C 2.2: tetrahydrofuran / 20 °C / Heating 3.1: 66 percent / BH3*NH3; n-BuLi / tetrahydrofuran / 20 °C 4.1: POCl3; DMF / toluene / 80 °C View Scheme |
(E)-3-[4-Methoxy-3-(3-methoxy-propoxy)-phenyl]-acrylic acid
(R)-2-[4-methoxy-3-(3-methoxypropoxyl)]phenylmethyl-3-methyl-1-chlorobutane
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1.1: H2 / Pd/C / ethyl acetate / 20 °C 2.1: (COCl)2 / dimethylformamide / 20 °C 3.1: NaOH / toluene / 20 °C 4.1: LDA; LiCl / tetrahydrofuran / 0 °C 4.2: tetrahydrofuran / 20 °C / Heating 5.1: 66 percent / BH3*NH3; n-BuLi / tetrahydrofuran / 20 °C 6.1: POCl3; DMF / toluene / 80 °C View Scheme |
(R)-3-[4-methoxy-3-(3-methoxypropoxy)phenyl]-2-(1-methylethyl)propanoic acid
(R)-2-[4-methoxy-3-(3-methoxypropoxyl)]phenylmethyl-3-methyl-1-chlorobutane
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 90 percent / NaBH4; I2 / 96 h / 20 °C 2: 70 percent / SOCl2; pyridine 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: N-chloro-succinimide; triphenylphosphine / dichloromethane / 5.5 h / -40 - 30 °C View Scheme | |
Multi-step reaction with 2 steps 1: sulfuric acid; sodium tetrahydroborate / tetrahydrofuran / 0 - 20 °C 2: thionyl chloride / toluene; N,N-dimethyl acetamide / 2.5 h / 89 - 95 °C View Scheme | |
Multi-step reaction with 2 steps 1.1: sodium tetrahydroborate / tetrahydrofuran / 1 h / 0 °C / Inert atmosphere; Large scale 1.2: 0 °C / Large scale 2.1: thionyl chloride; sodium hydroxide / toluene; N,N-dimethyl-formamide / 0.5 h / 90 °C / Inert atmosphere; Large scale View Scheme |
N-(2-hydroxy-1-methyl-2-phenyl-ethyl)-3-[4-methoxy-3-(3-methoxy-propoxy)-phenyl]-N-methyl-propionamide
(R)-2-[4-methoxy-3-(3-methoxypropoxyl)]phenylmethyl-3-methyl-1-chlorobutane
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: LDA; LiCl / tetrahydrofuran / 0 °C 1.2: tetrahydrofuran / 20 °C / Heating 2.1: 66 percent / BH3*NH3; n-BuLi / tetrahydrofuran / 20 °C 3.1: POCl3; DMF / toluene / 80 °C View Scheme |
N-(2-hydroxy-1-methyl-2-phenyl-ethyl)-2-[4-methoxy-3-(3-methoxy-propoxy)-benzyl]-3,N-dimethyl-butyramide
(R)-2-[4-methoxy-3-(3-methoxypropoxyl)]phenylmethyl-3-methyl-1-chlorobutane
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 66 percent / BH3*NH3; n-BuLi / tetrahydrofuran / 20 °C 2: POCl3; DMF / toluene / 80 °C View Scheme |
3-methylbutyric acid
(R)-2-[4-methoxy-3-(3-methoxypropoxyl)]phenylmethyl-3-methyl-1-chlorobutane
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: N-chloro-succinimide; triphenylphosphine / 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: N-chloro-succinimide; triphenylphosphine / 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: N-chloro-succinimide; triphenylphosphine / 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: N-chloro-succinimide; triphenylphosphine / dichloromethane / 5.5 h / -40 - 30 °C View Scheme |
4-(bromomethyl)-1-methoxy-2-(3-methoxypropoxy)-benzene
(R)-2-[4-methoxy-3-(3-methoxypropoxyl)]phenylmethyl-3-methyl-1-chlorobutane
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: N-chloro-succinimide; triphenylphosphine / 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: N-chloro-succinimide; triphenylphosphine / dichloromethane / 5.5 h / -40 - 30 °C View Scheme | |
Multi-step reaction with 4 steps 1.1: lithium hexamethyldisilazane / tetrahydrofuran / 1 h / -10 °C / Inert atmosphere; Large scale 1.2: 20 h / 0 °C / Large scale 2.1: dihydrogen peroxide / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere; Large scale 2.2: Large scale 3.1: sodium tetrahydroborate / tetrahydrofuran / 1 h / 0 °C / Inert atmosphere; Large scale 3.2: 0 °C / Large scale 4.1: thionyl chloride; sodium hydroxide / toluene; N,N-dimethyl-formamide / 0.5 h / 90 °C / Inert atmosphere; Large scale View Scheme |
[4-methoxy-3-(3-methoxypropoxy)-phenyl]methanol
(R)-2-[4-methoxy-3-(3-methoxypropoxyl)]phenylmethyl-3-methyl-1-chlorobutane
Conditions | Yield |
---|---|
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: N-chloro-succinimide; triphenylphosphine / dichloromethane / 5.5 h / -40 - 30 °C View Scheme | |
Multi-step reaction with 4 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: sodium tetrahydroborate / tetrahydrofuran / 0 - 15 °C 3.2: 11 h / 60 - 65 °C 4.1: N-chloro-succinimide; triphenylphosphine / dichloromethane / 5.5 h / -40 - 30 °C View Scheme | |
Multi-step reaction with 5 steps 1.1: thionyl chloride / dichloromethane / 2 h / 0 °C 2.1: sodium iodide / tetrahydrofuran / 16 h / 25 - 30 °C 3.1: 1,1,1,3,3,3-hexamethyl-disilazane; n-butyllithium / tetrahydrofuran; hexane / 1 h / Cooling with ice; Inert atmosphere 3.2: 16 h / -30 - -5 °C 4.1: sodium tetrahydroborate / tetrahydrofuran; water / 20 °C 5.1: thionyl chloride / toluene; N,N-dimethyl acetamide / 1.5 h / 89 - 95 °C View Scheme | |
Multi-step reaction with 6 steps 1.1: thionyl chloride / dichloromethane / 3 h / 0 - 5 °C 2.1: sodium iodide / tetrahydrofuran / 16 h / 25 - 30 °C 3.1: lithium diisopropyl amide / tetrahydrofuran; hexane / -78 - -45 °C / Inert atmosphere 3.2: 1 h / -45 - -20 °C 4.1: dihydrogen peroxide; lithium hydrochloride monohydrate; water / tetrahydrofuran / 0 - 25 °C 5.1: sulfuric acid; sodium tetrahydroborate / tetrahydrofuran / 0 - 20 °C 6.1: thionyl chloride / toluene; N,N-dimethyl acetamide / 2.5 h / 89 - 95 °C View Scheme | |
Multi-step reaction with 5 steps 1.1: phosphorus tribromide / dichloromethane / 0 - 5 °C / Inert atmosphere; Large scale 2.1: lithium hexamethyldisilazane / tetrahydrofuran / 1 h / -10 °C / Inert atmosphere; Large scale 2.2: 20 h / 0 °C / Large scale 3.1: dihydrogen peroxide / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere; Large scale 3.2: Large scale 4.1: sodium tetrahydroborate / tetrahydrofuran / 1 h / 0 °C / Inert atmosphere; Large scale 4.2: 0 °C / Large scale 5.1: thionyl chloride; sodium hydroxide / toluene; N,N-dimethyl-formamide / 0.5 h / 90 °C / Inert atmosphere; Large scale View Scheme |
(R)-2-[4-methoxy-3-(3-methoxypropoxyl)]phenylmethyl-3-methyl-1-chlorobutane
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: N-chloro-succinimide; triphenylphosphine / 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: N-chloro-succinimide; triphenylphosphine / 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: N-chloro-succinimide; triphenylphosphine / 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: N-chloro-succinimide; triphenylphosphine / 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)-2-[4-methoxy-3-(3-methoxypropoxyl)]phenylmethyl-3-methyl-1-chlorobutane
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: N-chloro-succinimide; triphenylphosphine / 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: N-chloro-succinimide; triphenylphosphine / dichloromethane / 5.5 h / -40 - 30 °C View Scheme | |
Multi-step reaction with 3 steps 1.1: dihydrogen peroxide / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere; Large scale 1.2: Large scale 2.1: sodium tetrahydroborate / tetrahydrofuran / 1 h / 0 °C / Inert atmosphere; Large scale 2.2: 0 °C / Large scale 3.1: thionyl chloride; sodium hydroxide / toluene; N,N-dimethyl-formamide / 0.5 h / 90 °C / Inert atmosphere; Large scale View Scheme |
(4R)-3-(2S)-(2-(hydroxy(4-methoxy-3-(3-methoxypropoxy)phenyl)methyl)-3-methylbutanoyl)-4-phenyloxazolidin-2-one
(R)-2-[4-methoxy-3-(3-methoxypropoxyl)]phenylmethyl-3-methyl-1-chlorobutane
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: N-chloro-succinimide; triphenylphosphine / 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: N-chloro-succinimide; triphenylphosphine / dichloromethane / 5.5 h / -40 - 30 °C View Scheme |
C12H17IO3
(R)-2-[4-methoxy-3-(3-methoxypropoxyl)]phenylmethyl-3-methyl-1-chlorobutane
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: 1,1,1,3,3,3-hexamethyl-disilazane; n-butyllithium / tetrahydrofuran; hexane / 1 h / Cooling with ice; Inert atmosphere 1.2: 16 h / -30 - -5 °C 2.1: sodium tetrahydroborate / tetrahydrofuran; water / 20 °C 3.1: thionyl chloride / toluene; N,N-dimethyl acetamide / 1.5 h / 89 - 95 °C View Scheme | |
Multi-step reaction with 4 steps 1.1: lithium diisopropyl amide / tetrahydrofuran; hexane / -78 - -45 °C / Inert atmosphere 1.2: 1 h / -45 - -20 °C 2.1: dihydrogen peroxide; lithium hydrochloride monohydrate; water / tetrahydrofuran / 0 - 25 °C 3.1: sulfuric acid; sodium tetrahydroborate / tetrahydrofuran / 0 - 20 °C 4.1: thionyl chloride / toluene; N,N-dimethyl acetamide / 2.5 h / 89 - 95 °C View Scheme |
(R)-2-[4-methoxy-3-(3-methoxypropoxyl)]phenylmethyl-3-methyl-1-chlorobutane
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: 1,1,1,3,3,3-hexamethyl-disilazane; n-butyllithium / tetrahydrofuran; hexane / 1 h / Cooling with ice; Inert atmosphere 1.2: 16 h / -30 - -5 °C 2.1: sodium tetrahydroborate / tetrahydrofuran; water / 20 °C 3.1: thionyl chloride / toluene; N,N-dimethyl acetamide / 1.5 h / 89 - 95 °C View Scheme |
isopentanoyl chloride
(R)-2-[4-methoxy-3-(3-methoxypropoxyl)]phenylmethyl-3-methyl-1-chlorobutane
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1.1: dmap; triethylamine / toluene / 0 - 25 °C 2.1: 1,1,1,3,3,3-hexamethyl-disilazane; n-butyllithium / tetrahydrofuran; hexane / 1 h / Cooling with ice; Inert atmosphere 2.2: 16 h / -30 - -5 °C 3.1: sodium tetrahydroborate / tetrahydrofuran; water / 20 °C 4.1: thionyl chloride / toluene; N,N-dimethyl acetamide / 1.5 h / 89 - 95 °C View Scheme | |
Multi-step reaction with 5 steps 1.1: sodium hydride / toluene / 4 h / 20 - 25 °C 1.2: 1.5 h / 15 - 30 °C 2.1: lithium diisopropyl amide / tetrahydrofuran; hexane / -78 - -45 °C / Inert atmosphere 2.2: 1 h / -45 - -20 °C 3.1: dihydrogen peroxide; lithium hydrochloride monohydrate; water / tetrahydrofuran / 0 - 25 °C 4.1: sulfuric acid; sodium tetrahydroborate / tetrahydrofuran / 0 - 20 °C 5.1: thionyl chloride / toluene; N,N-dimethyl acetamide / 2.5 h / 89 - 95 °C View Scheme | |
Multi-step reaction with 5 steps 1.1: sodium hydride / tetrahydrofuran; mineral oil / 15 - 30 °C / Inert atmosphere; Large scale 2.1: lithium hexamethyldisilazane / tetrahydrofuran / 1 h / -10 °C / Inert atmosphere; Large scale 2.2: 20 h / 0 °C / Large scale 3.1: dihydrogen peroxide / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere; Large scale 3.2: Large scale 4.1: sodium tetrahydroborate / tetrahydrofuran / 1 h / 0 °C / Inert atmosphere; Large scale 4.2: 0 °C / Large scale 5.1: thionyl chloride; sodium hydroxide / toluene; N,N-dimethyl-formamide / 0.5 h / 90 °C / Inert atmosphere; Large scale View Scheme |
4-chloromethyl-1-methoxy-2-(3-methoxypropoxy)-benzene
(R)-2-[4-methoxy-3-(3-methoxypropoxyl)]phenylmethyl-3-methyl-1-chlorobutane
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1.1: sodium iodide / tetrahydrofuran / 16 h / 25 - 30 °C 2.1: 1,1,1,3,3,3-hexamethyl-disilazane; n-butyllithium / tetrahydrofuran; hexane / 1 h / Cooling with ice; Inert atmosphere 2.2: 16 h / -30 - -5 °C 3.1: sodium tetrahydroborate / tetrahydrofuran; water / 20 °C 4.1: thionyl chloride / toluene; N,N-dimethyl acetamide / 1.5 h / 89 - 95 °C View Scheme | |
Multi-step reaction with 5 steps 1.1: sodium iodide / tetrahydrofuran / 16 h / 25 - 30 °C 2.1: lithium diisopropyl amide / tetrahydrofuran; hexane / -78 - -45 °C / Inert atmosphere 2.2: 1 h / -45 - -20 °C 3.1: dihydrogen peroxide; lithium hydrochloride monohydrate; water / tetrahydrofuran / 0 - 25 °C 4.1: sulfuric acid; sodium tetrahydroborate / tetrahydrofuran / 0 - 20 °C 5.1: thionyl chloride / toluene; N,N-dimethyl acetamide / 2.5 h / 89 - 95 °C View Scheme |
(R)-4-benzyl-3-(3-methylbutyryl)oxazolidin-2-one
(R)-2-[4-methoxy-3-(3-methoxypropoxyl)]phenylmethyl-3-methyl-1-chlorobutane
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1.1: lithium diisopropyl amide / tetrahydrofuran; hexane / -78 - -45 °C / Inert atmosphere 1.2: 1 h / -45 - -20 °C 2.1: dihydrogen peroxide; lithium hydrochloride monohydrate; water / tetrahydrofuran / 0 - 25 °C 3.1: sulfuric acid; sodium tetrahydroborate / tetrahydrofuran / 0 - 20 °C 4.1: thionyl chloride / toluene; N,N-dimethyl acetamide / 2.5 h / 89 - 95 °C View Scheme |
(4R)-3-{(2R)-2-{[4-methoxy-3-(methoxypropoxy)phenyl]methyl-3-methyl}-1-oxobutyl}-4-(phenylmethyl)oxazolidin-2-one
(R)-2-[4-methoxy-3-(3-methoxypropoxyl)]phenylmethyl-3-methyl-1-chlorobutane
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: dihydrogen peroxide; lithium hydrochloride monohydrate; water / tetrahydrofuran / 0 - 25 °C 2: sulfuric acid; sodium tetrahydroborate / tetrahydrofuran / 0 - 20 °C 3: thionyl chloride / toluene; N,N-dimethyl acetamide / 2.5 h / 89 - 95 °C View Scheme |
isovanillin
(R)-2-[4-methoxy-3-(3-methoxypropoxyl)]phenylmethyl-3-methyl-1-chlorobutane
Conditions | Yield |
---|---|
Multi-step reaction with 8 steps 1.1: potassium carbonate / toluene; dimethyl sulfoxide / 16 h / 25 - 90 °C 2.1: sodium tetrahydroborate / toluene; methanol / 3 h / 0 - 5 °C 3.1: thionyl chloride / dichloromethane / 3 h / 0 - 5 °C 4.1: sodium iodide / tetrahydrofuran / 16 h / 25 - 30 °C 5.1: lithium diisopropyl amide / tetrahydrofuran; hexane / -78 - -45 °C / Inert atmosphere 5.2: 1 h / -45 - -20 °C 6.1: dihydrogen peroxide; lithium hydrochloride monohydrate; water / tetrahydrofuran / 0 - 25 °C 7.1: sulfuric acid; sodium tetrahydroborate / tetrahydrofuran / 0 - 20 °C 8.1: thionyl chloride / toluene; N,N-dimethyl acetamide / 2.5 h / 89 - 95 °C View Scheme |
(R)-2-[4-methoxy-3-(3-methoxypropoxyl)]phenylmethyl-3-methyl-1-chlorobutane
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1.1: lithium hexamethyldisilazane / tetrahydrofuran / 1 h / -10 °C / Inert atmosphere; Large scale 1.2: 20 h / 0 °C / Large scale 2.1: dihydrogen peroxide / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere; Large scale 2.2: Large scale 3.1: sodium tetrahydroborate / tetrahydrofuran / 1 h / 0 °C / Inert atmosphere; Large scale 3.2: 0 °C / Large scale 4.1: thionyl chloride; sodium hydroxide / toluene; N,N-dimethyl-formamide / 0.5 h / 90 °C / Inert atmosphere; Large scale View Scheme |
ethylene dibromide
(R)-2-[4-methoxy-3-(3-methoxypropoxyl)]phenylmethyl-3-methyl-1-chlorobutane
Conditions | Yield |
---|---|
Stage #1: ethylene dibromide With magnesium In tetrahydrofuran at 60℃; Mg was added over a period of 2 min; Stage #2: ethylene dibromide; (R)-2-[4-methoxy-3-(3-methoxypropoxyl)]phenylmethyl-3-methyl-1-chlorobutane In tetrahydrofuran for 0.5h; Adding at 62-64 °ree;C; Heating / reflux; Stage #3: C10H18ClNO; 1-methyl-pyrrolidin-2-one; iron-(III)-acetylacetonate In tetrahydrofuran at 0 - 10℃; for 0.25h; Adding at -5-0 °ree;C; | 81% |
(R)-2-[4-methoxy-3-(3-methoxypropoxyl)]phenylmethyl-3-methyl-1-chlorobutane
(R)-4-(2-(iodomethyl)-3-methylbutyl)-1-methoxy-2-(3-methoxypropoxy)benzene
Conditions | Yield |
---|---|
With sodium iodide In acetone at 20 - 56℃; for 240h; | 80.5% |
(2S,4E)-5-chloro-2-isopropyl-N,N-dimethylpent-4-enamide
(R)-2-[4-methoxy-3-(3-methoxypropoxyl)]phenylmethyl-3-methyl-1-chlorobutane
(2S,7R,E)-2-isopropyl-7-(4-methoxy-3-(3-methoxypropoxy)benzyl)-N,N,8-trimethylnon-4-enamide
Conditions | Yield |
---|---|
Stage #1: (R)-2-[4-methoxy-3-(3-methoxypropoxyl)]phenylmethyl-3-methyl-1-chlorobutane With magnesium; ethylene dibromide In 2-methyltetrahydrofuran at 60 - 65℃; Stage #2: (2S,4E)-5-chloro-2-isopropyl-N,N-dimethylpent-4-enamide; iron(III)-acetylacetonate In 2-methyltetrahydrofuran; 1-methyl-pyrrolidin-2-one at 10℃; for 0.25h; Product distribution / selectivity; | 80% |
Stage #1: (R)-2-[4-methoxy-3-(3-methoxypropoxyl)]phenylmethyl-3-methyl-1-chlorobutane With magnesium; ethylene dibromide In tetrahydrofuran at 63 - 68℃; for 4.16667h; Inert atmosphere; Stage #2: (2S,4E)-5-chloro-2-isopropyl-N,N-dimethylpent-4-enamide; iron(III)-acetylacetonate In tetrahydrofuran; 1-methyl-pyrrolidin-2-one at 0 - 5℃; for 1h; | |
Stage #1: (R)-2-[4-methoxy-3-(3-methoxypropoxyl)]phenylmethyl-3-methyl-1-chlorobutane With iodine; methylmagnesium chloride; magnesium; 1-Bromo-2-chloroethane In tetrahydrofuran at 60℃; Reflux; Stage #2: (2S,4E)-5-chloro-2-isopropyl-N,N-dimethylpent-4-enamide With 1-methyl-pyrrolidin-2-one; iron(III)-acetylacetonate In tetrahydrofuran at 0 - 30℃; for 2h; | 120 g |
Stage #1: (R)-2-[4-methoxy-3-(3-methoxypropoxyl)]phenylmethyl-3-methyl-1-chlorobutane With methylmagnesium chloride; magnesium; ethylene dibromide In tetrahydrofuran at 60 - 65℃; Inert atmosphere; Industrial scale; Stage #2: (2S,4E)-5-chloro-2-isopropyl-N,N-dimethylpent-4-enamide With iron(III)-acetylacetonate In tetrahydrofuran; 1-methyl-pyrrolidin-2-one at 0 - 5℃; Concentration; Reagent/catalyst; Temperature; Time; Kumada Cross-Coupling; Inert atmosphere; Industrial scale; | |
Stage #1: (R)-2-[4-methoxy-3-(3-methoxypropoxyl)]phenylmethyl-3-methyl-1-chlorobutane With magnesium; ethylene dibromide In tetrahydrofuran at 65℃; Inert atmosphere; Stage #2: (2S,4E)-5-chloro-2-isopropyl-N,N-dimethylpent-4-enamide With 1-Methylpyrrolidine; iron(III)-acetylacetonate In tetrahydrofuran at -5 - 20℃; | 6.5 g |
(2S,3S,5R,7S,9S)-9-Isopropyl-3,4-dimethyl-2-phenyl-1,6-dioxa-4-aza-spiro[4.4]nonane-7-carbaldehyde
(R)-2-[4-methoxy-3-(3-methoxypropoxyl)]phenylmethyl-3-methyl-1-chlorobutane
A
(3S,5S)-5-{(1R,3S)-1-Hydroxy-3-[4-methoxy-3-(3-methoxy-propoxy)-benzyl]-4-methyl-pentyl}-3-isopropyl-dihydro-furan-2-one
B
(3S,5S)-dihydro-5-{(1S,3S)-1-hydroxy-3-{[4-methoxy-3-(3-methoxypropoxy)phenyl]methyl}-4-methylpentyl}-3-(1-methylethyl)furan-2(3H)-one
Conditions | Yield |
---|---|
Multistep reaction; | A 51% B n/a |
diethyl malonate
(R)-2-[4-methoxy-3-(3-methoxypropoxyl)]phenylmethyl-3-methyl-1-chlorobutane
C24H38O7
Conditions | Yield |
---|---|
With sodium ethanolate; sodium iodide In ethanol | 37% |
(S)-tetrahydro-5-oxo-2-furancarbonyl chloride
(R)-2-[4-methoxy-3-(3-methoxypropoxyl)]phenylmethyl-3-methyl-1-chlorobutane
(S)-5-{(S)-3-[4-Methoxy-3-(3-methoxy-propoxy)-benzyl]-4-methyl-pentanoyl}-dihydro-furan-2-one
Conditions | Yield |
---|---|
With magnesium; ethylene dibromide In tetrahydrofuran at 20℃; |
tetrahydro-4-isopropyl-5-oxofuran-2-carbonyl chloride
(R)-2-[4-methoxy-3-(3-methoxypropoxyl)]phenylmethyl-3-methyl-1-chlorobutane
(3S,5S)-3-Isopropyl-5-{(S)-3-[4-methoxy-3-(3-methoxy-propoxy)-benzyl]-4-methyl-pentanoyl}-dihydro-furan-2-one
Conditions | Yield |
---|---|
With magnesium; ethylene dibromide In tetrahydrofuran at 20℃; | |
Stage #1: (R)-2-[4-methoxy-3-(3-methoxypropoxyl)]phenylmethyl-3-methyl-1-chlorobutane With magnesium; iodine In tetrahydrofuran; 1,2-dibromomethane for 5h; Inert atmosphere; Heating; Reflux; Stage #2: tetrahydro-4-isopropyl-5-oxofuran-2-carbonyl chloride In tetrahydrofuran at 22℃; for 0.5h; Cooling with ice/water bath; Stage #3: With water In tetrahydrofuran Cooling with ice; |
(R)-2-[4-methoxy-3-(3-methoxypropoxyl)]phenylmethyl-3-methyl-1-chlorobutane
C25H32N2O3
A
N-Benzyl-N-{(1S,3S)-1-((2S,3S,5S,7S,9S)-9-isopropyl-3,4-dimethyl-2-phenyl-1,6-dioxa-4-aza-spiro[4.4]non-7-yl)-3-[4-methoxy-3-(3-methoxy-propoxy)-benzyl]-4-methyl-pentyl}-hydroxylamine
B
N-Benzyl-N-{(1R,3S)-1-((2S,3S,5S,7S,9S)-9-isopropyl-3,4-dimethyl-2-phenyl-1,6-dioxa-4-aza-spiro[4.4]non-7-yl)-3-[4-methoxy-3-(3-methoxy-propoxy)-benzyl]-4-methyl-pentyl}-hydroxylamine
Conditions | Yield |
---|---|
Stage #1: (R)-2-[4-methoxy-3-(3-methoxypropoxyl)]phenylmethyl-3-methyl-1-chlorobutane With magnesium; ethylene dibromide In tetrahydrofuran at 45℃; for 1h; Stage #2: C25H32N2O3 In tetrahydrofuran at -40℃; for 15h; | |
Stage #1: (R)-2-[4-methoxy-3-(3-methoxypropoxyl)]phenylmethyl-3-methyl-1-chlorobutane With magnesium; ethylene dibromide In tetrahydrofuran at 45℃; for 1h; Stage #2: C25H32N2O3 With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone In tetrahydrofuran at -10℃; for 15h; | |
Stage #1: (R)-2-[4-methoxy-3-(3-methoxypropoxyl)]phenylmethyl-3-methyl-1-chlorobutane With magnesium; iodine; ethylene dibromide In tetrahydrofuran at 75℃; for 2.25h; Stage #2: C25H32N2O3 In tetrahydrofuran at -10℃; for 15h; | A n/a B n/a |
Stage #1: (R)-2-[4-methoxy-3-(3-methoxypropoxyl)]phenylmethyl-3-methyl-1-chlorobutane With cerium(III) chloride Stage #2: C25H32N2O3 | A n/a B n/a |
(R)-2-[4-methoxy-3-(3-methoxypropoxyl)]phenylmethyl-3-methyl-1-chlorobutane
(S)-5-{(1S,3S)-1-Hydroxy-3-[4-methoxy-3-(3-methoxy-propoxy)-benzyl]-4-methyl-pentyl}-dihydro-furan-2-one
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: Mg; BrCH2CH2Br / tetrahydrofuran / 20 °C 2: K-Selectride / tetrahydrofuran / -78 - 0 °C View Scheme |
(R)-2-[4-methoxy-3-(3-methoxypropoxyl)]phenylmethyl-3-methyl-1-chlorobutane
(S)-5-{(1R,3S)-1-Hydroxy-3-[4-methoxy-3-(3-methoxy-propoxy)-benzyl]-4-methyl-pentyl}-dihydro-furan-2-one
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: Mg; BrCH2CH2Br / tetrahydrofuran / 20 °C 2: K-Selectride / tetrahydrofuran / -78 - 0 °C View Scheme |
(R)-2-[4-methoxy-3-(3-methoxypropoxyl)]phenylmethyl-3-methyl-1-chlorobutane
(3S,5S)-5-{(1R,3S)-1-Hydroxy-3-[4-methoxy-3-(3-methoxy-propoxy)-benzyl]-4-methyl-pentyl}-3-isopropyl-dihydro-furan-2-one
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: Mg; BrCH2CH2Br / tetrahydrofuran / 20 °C 2: H2 / [Ru2Cl4((S)-BINAP)]NEt3 / methanol / 40 h / 40 °C / 37503 Torr View Scheme |
(R)-2-[4-methoxy-3-(3-methoxypropoxyl)]phenylmethyl-3-methyl-1-chlorobutane
(3S,5S)-dihydro-5-{(1S,3S)-1-hydroxy-3-{[4-methoxy-3-(3-methoxypropoxy)phenyl]methyl}-4-methylpentyl}-3-(1-methylethyl)furan-2(3H)-one
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: Mg; BrCH2CH2Br / tetrahydrofuran / 20 °C 2: H2 / [Ru2Cl4((S)-BINAP)]NEt3 / methanol / 40 h / 40 °C / 37503 Torr View Scheme |
(R)-2-[4-methoxy-3-(3-methoxypropoxyl)]phenylmethyl-3-methyl-1-chlorobutane
(3S,5S)-5-((1S,3S)-1-azido-3-(4-methoxy-3-(3-methoxypropoxy)benzyl)-4-methylpentyl)-3-isopropyldihydrofuran-2(3H)-one
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: Mg; BrCH2CH2Br / tetrahydrofuran / 20 °C 2: H2 / [Ru2Cl4((S)-BINAP)]NEt3 / methanol / 40 h / 40 °C / 37503 Torr 3: NEt3 / CH2Cl2 4: 85 percent / NaN3; 15-crown-6; DMPU View Scheme | |
Multi-step reaction with 5 steps 1.1: magnesium; ethylene dibromide / tetrahydrofuran / 4.17 h / 63 - 68 °C / Inert atmosphere 1.2: 12.5 h / 0 - 5 °C 2.1: water; lithium hydroxide / tetrahydrofuran; methanol / 26 h / 65 - 70 °C 2.2: 0.5 h / 0 - 5 °C 3.1: hydrogenchloride / 1,1-dichloroethane; water / 0 - 5 °C / pH 2.5 3.2: 14.25 h / 0 - 30 °C 4.1: N-Bromosuccinimide; phosphoric acid / water; tetrahydrofuran / 1.25 h / 0 - 5 °C 5.1: sodium azide / ethylene glycol / 20 h / 80 - 85 °C View Scheme | |
Multi-step reaction with 2 steps 1.1: magnesium; ethylene dibromide / tetrahydrofuran / 4.17 h / 63 - 68 °C / Inert atmosphere 1.2: 1 h / 0 - 5 °C 1.3: 0.75 h / 0 - 5 °C 2.1: sodium azide / ethylene glycol / 20 h / 80 - 85 °C View Scheme |
(R)-2-[4-methoxy-3-(3-methoxypropoxyl)]phenylmethyl-3-methyl-1-chlorobutane
(3S,5S)-5-{(1S,3S)-1-azido-3-{[4-methoxy-3-(3-methoxypropoxy)phenyl]methyl}-4-methylpentyl}-dihydro-3-(1-methylethyl)furan-2(3H)-one
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: Mg; BrCH2CH2Br / tetrahydrofuran / 20 °C 2: H2 / [Ru2Cl4((S)-BINAP)]NEt3 / methanol / 40 h / 40 °C / 37503 Torr 3: NEt3 / CH2Cl2 4: 85 percent / NaN3; 15-crown-6; DMPU View Scheme | |
Multi-step reaction with 3 steps 1: 51 percent 2: DMAP / CH2Cl2 / 20 °C 3: NaN3; NMP / 60 °C View Scheme | |
Multi-step reaction with 3 steps 1.1: magnesium; ethylene dibromide / 2-methyltetrahydrofuran / 60 - 65 °C 1.2: 0.25 h / 10 °C 2.1: N-Bromosuccinimide; phosphoric acid / water; tetrahydrofuran / 5 °C 3.1: sodium azide; Aliquat 336 / water / 48 h / 75 - 80 °C View Scheme | |
Multi-step reaction with 3 steps 1.1: magnesium; ethylene dibromide / tetrahydrofuran / 65 °C / Inert atmosphere 1.2: -5 - 20 °C 2.1: N-Bromosuccinimide; phosphoric acid / tetrahydrofuran; water / 2 h / 0 - 10 °C / Inert atmosphere 3.1: sodium azide / 2,2'-[1,2-ethanediylbis(oxy)]bisethanol / 72 h / 90 °C / Inert atmosphere View Scheme |
(R)-2-[4-methoxy-3-(3-methoxypropoxyl)]phenylmethyl-3-methyl-1-chlorobutane
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: Mg; BrCH2CH2Br / tetrahydrofuran / 20 °C 2: 89 percent / NaHCO3 3: 74 percent / H2 / Pd/C / methanol View Scheme | |
Multi-step reaction with 2 steps 1: Mg; BrCH2CH2Br / tetrahydrofuran / 20 °C 2: 81 percent / NH2OH*HCl; NaHCO3 / methanol / 20 °C View Scheme |
(R)-2-[4-methoxy-3-(3-methoxypropoxyl)]phenylmethyl-3-methyl-1-chlorobutane
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: Mg; BrCH2CH2Br / tetrahydrofuran / 20 °C 2: K-Selectride / tetrahydrofuran / -78 - 0 °C 3: NEt3 / CH2Cl2 View Scheme |
(R)-2-[4-methoxy-3-(3-methoxypropoxyl)]phenylmethyl-3-methyl-1-chlorobutane
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: Mg; BrCH2CH2Br / tetrahydrofuran / 20 °C 2: K-Selectride / tetrahydrofuran / -78 - 0 °C 3: NEt3 / CH2Cl2 View Scheme |
(R)-2-[4-methoxy-3-(3-methoxypropoxyl)]phenylmethyl-3-methyl-1-chlorobutane
Methanesulfonic acid (1R,3S)-1-((2S,4S)-4-isopropyl-5-oxo-tetrahydro-furan-2-yl)-3-[4-methoxy-3-(3-methoxy-propoxy)-benzyl]-4-methyl-pentyl ester
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: Mg; BrCH2CH2Br / tetrahydrofuran / 20 °C 2: H2 / [Ru2Cl4((S)-BINAP)]NEt3 / methanol / 40 h / 40 °C / 37503 Torr 3: NEt3 / CH2Cl2 View Scheme |
(R)-2-[4-methoxy-3-(3-methoxypropoxyl)]phenylmethyl-3-methyl-1-chlorobutane
Methanesulfonic acid (1S,3S)-1-((2S,4S)-4-isopropyl-5-oxo-tetrahydro-furan-2-yl)-3-[4-methoxy-3-(3-methoxy-propoxy)-benzyl]-4-methyl-pentyl ester
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: Mg; BrCH2CH2Br / tetrahydrofuran / 20 °C 2: H2 / [Ru2Cl4((S)-BINAP)]NEt3 / methanol / 40 h / 40 °C / 37503 Torr 3: NEt3 / CH2Cl2 View Scheme |
(R)-2-[4-methoxy-3-(3-methoxypropoxyl)]phenylmethyl-3-methyl-1-chlorobutane
(3S,5S)-5-{(S)-1-[(Z)-Benzyloxyimino]-3-[4-methoxy-3-(3-methoxy-propoxy)-benzyl]-4-methyl-pentyl}-3-isopropyl-dihydro-furan-2-one
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: Mg; BrCH2CH2Br / tetrahydrofuran / 20 °C 2: 89 percent / NaHCO3 View Scheme |
(R)-2-[4-methoxy-3-(3-methoxypropoxyl)]phenylmethyl-3-methyl-1-chlorobutane
4-Bromo-benzenesulfonic acid (1R,3S)-1-((2S,4S)-4-isopropyl-5-oxo-tetrahydro-furan-2-yl)-3-[4-methoxy-3-(3-methoxy-propoxy)-benzyl]-4-methyl-pentyl ester
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 51 percent 2: DMAP / CH2Cl2 / 20 °C View Scheme |
(R)-2-[4-methoxy-3-(3-methoxypropoxyl)]phenylmethyl-3-methyl-1-chlorobutane
(2S,4S,5R,7S)-5-amino-N-(2-carbamoyl-2-methylpropyl)-4-hydroxy-7-(4-methoxy-3-(3-methoxypropoxy)benzyl)-8-methyl-2-isopropylnonanamide
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1: Mg; BrCH2CH2Br / tetrahydrofuran / 20 °C 2: H2 / [Ru2Cl4((S)-BINAP)]NEt3 / methanol / 40 h / 40 °C / 37503 Torr 3: NEt3 / CH2Cl2 4: 85 percent / NaN3; 15-crown-6; DMPU 5: 59 percent / 2-OH-pyridine; NEt3 6: H2; aq. HCl / Pd/C / methanol View Scheme |
(R)-2-[4-methoxy-3-(3-methoxypropoxyl)]phenylmethyl-3-methyl-1-chlorobutane
(2S,4S,5S,7S)-5-Amino-4-hydroxy-2-isopropyl-7-[4-methoxy-3-(3-methoxy-propoxy)-benzyl]-8-methyl-nonanoic acid (2-carbamoyl-2-methyl-propyl)-amide
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1: Mg; BrCH2CH2Br / tetrahydrofuran / 20 °C 2: H2 / [Ru2Cl4((S)-BINAP)]NEt3 / methanol / 40 h / 40 °C / 37503 Torr 3: NEt3 / CH2Cl2 4: 85 percent / NaN3; 15-crown-6; DMPU 5: 59 percent / 2-OH-pyridine; NEt3 6: H2; aq. HCl / Pd/C / methanol View Scheme | |
Multi-step reaction with 13 steps 1.1: sodium ethanolate; sodium iodide / ethanol 2.1: potassium acetate / water; dimethyl sulfoxide 3.1: sodium hydroxide 4.1: thionyl chloride 5.1: pyridine / 12 h / 40 °C 6.1: dicyclohexyl(trifluoromethylsulfonyloxy)borane; triethylamine / -78 - 0 °C 7.1: dihydrogen peroxide; lithium hydroxide / tetrahydrofuran; water / 0.25 h 7.2: Acidic aq. solution 8.1: water; lithium hydroxide / 1,4-dioxane / 120 h / 40 °C 9.1: diphenyl phosphoryl azide; triethylamine / toluene / 0.33 h / 20 °C 10.1: diphenyl phosphoryl azide; triethylamine / toluene / 1 h / 65 °C 11.1: 1.5 h / 65 °C 12.1: 2-hydroxypyridin / tert-butyl methyl ether / 65 °C 13.1: 10% palladium on activated charcoal; hydrogen View Scheme | |
Multi-step reaction with 7 steps 1.1: magnesium; ethylene dibromide / tetrahydrofuran / 4.17 h / 63 - 68 °C / Inert atmosphere 1.2: 12.5 h / 0 - 5 °C 2.1: water; lithium hydroxide / tetrahydrofuran; methanol / 26 h / 65 - 70 °C 2.2: 0.5 h / 0 - 5 °C 3.1: hydrogenchloride / 1,1-dichloroethane; water / 0 - 5 °C / pH 2.5 3.2: 14.25 h / 0 - 30 °C 4.1: N-Bromosuccinimide; phosphoric acid / water; tetrahydrofuran / 1.25 h / 0 - 5 °C 5.1: sodium azide / ethylene glycol / 20 h / 80 - 85 °C 6.1: triethylamine; 2-hydroxypyridin / 16 h / 85 - 90 °C 7.1: hydrogen; ethanolamine / palladium 10% on activated carbon / isopropyl alcohol / 3 h View Scheme |
(R)-2-[4-methoxy-3-(3-methoxypropoxyl)]phenylmethyl-3-methyl-1-chlorobutane
(2S,4S,5R,7S)-5-Azido-4-hydroxy-2-isopropyl-7-[4-methoxy-3-(3-methoxy-propoxy)-benzyl]-8-methyl-nonanoic acid (2-carbamoyl-2-methyl-propyl)-amide
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: Mg; BrCH2CH2Br / tetrahydrofuran / 20 °C 2: H2 / [Ru2Cl4((S)-BINAP)]NEt3 / methanol / 40 h / 40 °C / 37503 Torr 3: NEt3 / CH2Cl2 4: 85 percent / NaN3; 15-crown-6; DMPU 5: 59 percent / 2-OH-pyridine; NEt3 View Scheme |
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