Packing: According to customer requirements Delivery time: In stock or depands Port of shipment: Ningbo/Shanghai/Qingdao OEM/ODM:Welcome Sample:We can offer our existing samples at once Appearance:Clear colorless liquid Storage:Refer to COA / M
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inquiryQ1:Can you give me a discount price Surely,It depend on your qty Q2:How can i get a sample free samples is available,but freight charges will be at your account and the charges will be return to you or deduct from your order in the future. Q3: How
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inquiryWhy is SINOWAY: 1) Specialized in pharmaceutical and healthcare industrial for 34 years. 2) ISO 9001:2015 & SGS audited supplier . 3) Accept various payment terms : T.T 30-60 days. 4) We have warehouse in USA with quickly shipment . 5) We c
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inquiryType: Vitamin K2(35),MK-7,CAS: 2124-57-4 Form: Powder Part: Seed Extraction Type: Solvent Extraction Packaging: Drum, Vacuum Packed, Other Place of Origin: S
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inquiryWe are: Focus on the research, production and sale of Plant and Animal extract, Medical intermediate, complete coverage six industries. Product grade: Medicine, Health care product, Cosmetics, Food,Feed, Biopesticide. Hot selling market: Europe,
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inquiryHebei yanxi chemical co., LTD is a professional research, development and production Cyromazine、lead diacetate trihydrate /Lead acetate trihydrateC、 2-phenylacetamide 、 4-Aminophenyl-1-phenethylpiperidine 、Citric acid monohydrate 、 Citric acid/c
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inquiryProduct Name:Vitamin K2 MK7 Appearance:Light yellow powder Assay: 0.5%-2% Shipping method: Fedex, DHL, TNT, Sea, Air or as you wish Type: natural and synthetic Package: Aluminum Foil Bag Hot Market: Europe, America, Asia Usage: Food,Cosmetics,
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inquiryZorui combines R&D, production and sales into its operations, While continuously providing high-quality raw materials, we also provide and optimize technical solutions for customers to achieve mutual benefit. We adhere to the "quality, integ
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inquiryColorcom is a global leader in industrial chemical manufacturing and is continuously innovating and transforming to exceed client expectations and industry standards. Colorcom prides itself on superior customer and technical focus, while focusing on
As a leading manufacturer and supplier of chemicals in China, DayangChem not only supply popular chemicals, but also DayangChem’s R&D center offer custom synthesis according to the contract research and development services for the fine c
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Advantage : LIDE PHARMACEUTICALS LIMITED is a professional chemicals and APIs leading manufacturer in China. Our core business line covers APIs, Intermediates, Herb extract, etc. We are specialized in chemical synthesis, process development of
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inquiryCAS: 2124-57-4 Chemical formula: C46H64O2 Molecular weight: 649 Density: 0.961 Melting point: 54 ° C Boiling point: bp0.0002 200 ° (some dec) Solubility: Chloroform (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly) Storage conditions:
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inquiryAppearance:Light yellow powder Storage:ln stock Package:25kg/Barrel Application:Very important fat-soluble vitamin Transportation:Express/Sea/Air Port:Any port of China
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inquiryVitamin K2(35) Basic information Product Name: Vitamin K2(35) Synonyms: MENAQUINONE-7;(all-E)-2-(3,7,11,15,19,23,27-Heptamethyl-2,6,10,14,18,22,26-octacosaheptaenyl)-3-methyl-1,4-naphthalenedione;Menaquinone K7;Vitamin K2(35);Vitamin MK 7;Menl
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Triumph has the complete production of G- KG - MT service chain,we can make the new technology into productivity quickly in the research and development of new products. Main Service 1.Own made fine chemical products 2.Out
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inquiryCompany Introduction 1. Established in 2005, with two independent business divisions: Fine chemicals division; Pharmaceutical division. 2. Main product: Optical brightener Textile auxiliary Dye stuff Pigments
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inquiryEstablished in May 2015, TaiChem Ltd. is initially invested by a British research and development company and started by PhDs back from aboard. The company is registered in China Medical City (CMC), Taizhou, Jiangsu Province, and the production site
2-(3,7,11,15,19,23,27-heptamethyloctacosa-2,6,10,14,18,22,26-heptaenyl)-1,4-dimethoxy-3-methylnaphthalene
menaquinone-7
Conditions | Yield |
---|---|
With ammonium cerium (IV) nitrate In water; acetonitrile at 20℃; for 4.08333h; | 80% |
With ammonium cerium (IV) nitrate In acetonitrile at 20℃; for 4.08333h; | 80% |
With ammonium cerium (IV) nitrate In water; acetonitrile at 0℃; for 0.75h; | 72% |
With ammonium cerium (IV) nitrate In dichloromethane; water; acetonitrile at 0℃; for 0.75h; | 0.753 g |
C50H74O2
menaquinone-7
Conditions | Yield |
---|---|
With ammonium cerium (IV) nitrate In dichloromethane; water; acetonitrile at 0℃; for 0.25h; | 72% |
2-(chloromethyl)-3-methylnaphthalene-1,4-dione
trimethylaluminum
menaquinone-7
Conditions | Yield |
---|---|
Stage #1: C33H52; trimethylaluminum With zirconocene dichloride In toluene at 0℃; for 1h; Stage #2: 2-(chloromethyl)-3-methylnaphthalene-1,4-dione With bis(triphenylphosphine)nickel(II) chloride; n-butyllithium In tetrahydrofuran; hexane at -20℃; for 1h; | 65% |
Conditions | Yield |
---|---|
Multi-step reaction with 10 steps 1.1: salicylic acid; selenium(IV) oxide; tert.-butylhydroperoxide / water; dichloromethane / 24 h / 0 - 20 °C 2.1: sodium tetrahydroborate / methanol; tetrahydrofuran / 0.75 h / -10 °C 3.1: phosphorus tribromide / tetrahydrofuran / 3 h / 0 °C / Inert atmosphere 4.1: N,N-dimethyl-formamide / 18 h / 20 °C / Darkness 5.1: potassium tert-butylate / tetrahydrofuran; N,N-dimethyl-formamide / 2.67 h / -78 °C 5.2: -78 - 20 °C 6.1: sodium hydroxide; water / methanol / 1 h / 20 °C / pH 12 7.1: phosphorus tribromide / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere; Cooling with acetone-dry ice 8.1: sodium hexamethyldisilazane / tetrahydrofuran; N,N-dimethyl-formamide / 0.5 h / -20 - 0 °C / Inert atmosphere; Cooling with acetone-dry ice 9.1: (1,2-bis(diphenylphosphino)ethane)palladium(II) chloride / tetrahydrofuran / 0.08 h / 0 °C / Cooling with acetone-dry ice; Inert atmosphere 9.2: 4.5 h / 0 °C / Inert atmosphere 10.1: ammonium cerium (IV) nitrate / water; dichloromethane; acetonitrile / 0.25 h / 0 °C View Scheme | |
Multi-step reaction with 11 steps 1.1: salicylic acid; selenium(IV) oxide; tert.-butylhydroperoxide / water; dichloromethane / 24 h / 0 - 20 °C 2.1: sodium tetrahydroborate / methanol; tetrahydrofuran / 0.75 h / -10 °C 3.1: phosphorus tribromide / tetrahydrofuran / 3 h / 0 °C / Inert atmosphere 4.1: N,N-dimethyl-formamide / 18 h / 20 °C / Darkness 5.1: potassium tert-butylate / tetrahydrofuran; N,N-dimethyl-formamide / 2.67 h / -78 °C 5.2: -78 - 20 °C 6.1: sodium hydroxide; water / methanol / 1 h / 20 °C / pH 12 7.1: (1,2-bis(diphenylphosphino)ethane)palladium(II) chloride; lithium triethylborohydride / tetrahydrofuran / 1.17 h / 0 °C / Inert atmosphere 8.1: phosphorus tribromide / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere; Cooling with acetone-dry ice 9.1: sodium hexamethyldisilazane / tetrahydrofuran; N,N-dimethyl-formamide / 0.83 h / -20 °C / Inert atmosphere; Cooling with acetone-dry ice 10.1: (1,2-bis(diphenylphosphino)ethane)palladium(II) chloride / tetrahydrofuran / 0.08 h / Inert atmosphere; Cooling with acetone-dry ice 10.2: 5 h / 0 °C / Inert atmosphere 11.1: ammonium cerium (IV) nitrate / water; dichloromethane; acetonitrile / 0.25 h / 0 °C View Scheme | |
Multi-step reaction with 11 steps 1.1: selenium(IV) oxide; salicylic acid; tert.-butylhydroperoxide / dichloromethane / 14 h / 0 °C 1.2: 2 h 2.1: methanesulfonyl chloride; triethylamine / tetrahydrofuran / 0.75 h / -45 - -40 °C 2.2: 2 h / 0 °C 3.1: n-butyllithium / tetrahydrofuran / 0.67 h / -78 °C / Inert atmosphere 3.2: Inert atmosphere 4.1: sodium methylate / methanol / 4 h / 0 °C 5.1: Dess-Martin periodane; water / dichloromethane; acetonitrile / 20 °C 6.1: hydrazine; potassium hydroxide / diethylene glycol / 4 h / 60 - 215 °C / Inert atmosphere; Reflux 7.1: triphenylphosphine; bromine / dichloromethane / 0 °C 8.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere 8.2: 12 h / Inert atmosphere 9.1: Dess-Martin periodane; water / dichloromethane; acetonitrile / 20 °C 10.1: hydrazine; potassium hydroxide / diethylene glycol / 4 h / 60 - 215 °C / Inert atmosphere; Reflux 11.1: ammonium cerium (IV) nitrate / water; acetonitrile / 4.08 h / 20 °C View Scheme |
E,E,E-12-hydroxyfarnesyl acetate
menaquinone-7
Conditions | Yield |
---|---|
Multi-step reaction with 8 steps 1.1: phosphorus tribromide / tetrahydrofuran / 3 h / 0 °C / Inert atmosphere 2.1: N,N-dimethyl-formamide / 18 h / 20 °C / Darkness 3.1: potassium tert-butylate / tetrahydrofuran; N,N-dimethyl-formamide / 2.67 h / -78 °C 3.2: -78 - 20 °C 4.1: sodium hydroxide; water / methanol / 1 h / 20 °C / pH 12 5.1: phosphorus tribromide / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere; Cooling with acetone-dry ice 6.1: sodium hexamethyldisilazane / tetrahydrofuran; N,N-dimethyl-formamide / 0.5 h / -20 - 0 °C / Inert atmosphere; Cooling with acetone-dry ice 7.1: (1,2-bis(diphenylphosphino)ethane)palladium(II) chloride / tetrahydrofuran / 0.08 h / 0 °C / Cooling with acetone-dry ice; Inert atmosphere 7.2: 4.5 h / 0 °C / Inert atmosphere 8.1: ammonium cerium (IV) nitrate / water; dichloromethane; acetonitrile / 0.25 h / 0 °C View Scheme | |
Multi-step reaction with 9 steps 1.1: phosphorus tribromide / tetrahydrofuran / 3 h / 0 °C / Inert atmosphere 2.1: N,N-dimethyl-formamide / 18 h / 20 °C / Darkness 3.1: potassium tert-butylate / tetrahydrofuran; N,N-dimethyl-formamide / 2.67 h / -78 °C 3.2: -78 - 20 °C 4.1: sodium hydroxide; water / methanol / 1 h / 20 °C / pH 12 5.1: (1,2-bis(diphenylphosphino)ethane)palladium(II) chloride; lithium triethylborohydride / tetrahydrofuran / 1.17 h / 0 °C / Inert atmosphere 6.1: phosphorus tribromide / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere; Cooling with acetone-dry ice 7.1: sodium hexamethyldisilazane / tetrahydrofuran; N,N-dimethyl-formamide / 0.83 h / -20 °C / Inert atmosphere; Cooling with acetone-dry ice 8.1: (1,2-bis(diphenylphosphino)ethane)palladium(II) chloride / tetrahydrofuran / 0.08 h / Inert atmosphere; Cooling with acetone-dry ice 8.2: 5 h / 0 °C / Inert atmosphere 9.1: ammonium cerium (IV) nitrate / water; dichloromethane; acetonitrile / 0.25 h / 0 °C View Scheme | |
Multi-step reaction with 10 steps 1.1: methanesulfonyl chloride; triethylamine / tetrahydrofuran / 0.75 h / -45 - -40 °C 1.2: 2 h / 0 °C 2.1: n-butyllithium / tetrahydrofuran / 0.67 h / -78 °C / Inert atmosphere 2.2: Inert atmosphere 3.1: sodium methylate / methanol / 4 h / 0 °C 4.1: Dess-Martin periodane; water / dichloromethane; acetonitrile / 20 °C 5.1: hydrazine; potassium hydroxide / diethylene glycol / 4 h / 60 - 215 °C / Inert atmosphere; Reflux 6.1: triphenylphosphine; bromine / dichloromethane / 0 °C 7.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere 7.2: 12 h / Inert atmosphere 8.1: Dess-Martin periodane; water / dichloromethane; acetonitrile / 20 °C 9.1: hydrazine; potassium hydroxide / diethylene glycol / 4 h / 60 - 215 °C / Inert atmosphere; Reflux 10.1: ammonium cerium (IV) nitrate / water; acetonitrile / 4.08 h / 20 °C View Scheme |
(2E,6E,10E)-3,7,11-trimethyl-12-(phenylsulfonyl)-dodeca-2,6,10-trien-1-yl acetate
menaquinone-7
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1.1: potassium tert-butylate / tetrahydrofuran; N,N-dimethyl-formamide / 2.67 h / -78 °C 1.2: -78 - 20 °C 2.1: sodium hydroxide; water / methanol / 1 h / 20 °C / pH 12 3.1: phosphorus tribromide / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere; Cooling with acetone-dry ice 4.1: sodium hexamethyldisilazane / tetrahydrofuran; N,N-dimethyl-formamide / 0.5 h / -20 - 0 °C / Inert atmosphere; Cooling with acetone-dry ice 5.1: (1,2-bis(diphenylphosphino)ethane)palladium(II) chloride / tetrahydrofuran / 0.08 h / 0 °C / Cooling with acetone-dry ice; Inert atmosphere 5.2: 4.5 h / 0 °C / Inert atmosphere 6.1: ammonium cerium (IV) nitrate / water; dichloromethane; acetonitrile / 0.25 h / 0 °C View Scheme | |
Multi-step reaction with 7 steps 1.1: potassium tert-butylate / tetrahydrofuran; N,N-dimethyl-formamide / 2.67 h / -78 °C 1.2: -78 - 20 °C 2.1: sodium hydroxide; water / methanol / 1 h / 20 °C / pH 12 3.1: (1,2-bis(diphenylphosphino)ethane)palladium(II) chloride; lithium triethylborohydride / tetrahydrofuran / 1.17 h / 0 °C / Inert atmosphere 4.1: phosphorus tribromide / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere; Cooling with acetone-dry ice 5.1: sodium hexamethyldisilazane / tetrahydrofuran; N,N-dimethyl-formamide / 0.83 h / -20 °C / Inert atmosphere; Cooling with acetone-dry ice 6.1: (1,2-bis(diphenylphosphino)ethane)palladium(II) chloride / tetrahydrofuran / 0.08 h / Inert atmosphere; Cooling with acetone-dry ice 6.2: 5 h / 0 °C / Inert atmosphere 7.1: ammonium cerium (IV) nitrate / water; dichloromethane; acetonitrile / 0.25 h / 0 °C View Scheme | |
Multi-step reaction with 7 steps 1.1: potassium tert-butylate / tetrahydrofuran; N,N-dimethyl-formamide / 2.5 h / -78 °C 1.2: -78 - 20 °C 2.1: sodium hydroxide / methanol; water / 1 h / 20 °C / pH 12 3.1: (1,2-bis(diphenylphosphanyl)ethane)dichloridopalladium(II); lithium triethylborohydride / tetrahydrofuran / 0 - 20 °C / Inert atmosphere 4.1: phosphorus tribromide / tetrahydrofuran / 3 h / 0 °C / Inert atmosphere 5.1: potassium tert-butylate / tetrahydrofuran; N,N-dimethyl-formamide / -20 °C 6.1: (1,2-bis(diphenylphosphanyl)ethane)dichloridopalladium(II); lithium triethylborohydride / tetrahydrofuran / 0 - 20 °C / Inert atmosphere 7.1: ammonium cerium (IV) nitrate / water; acetonitrile / 0.75 h / 0 °C View Scheme | |
Multi-step reaction with 7 steps 1.1: potassium tert-butylate / tetrahydrofuran; N,N-dimethyl-formamide / 2.5 h / -78 °C 1.2: -78 - 20 °C 2.1: sodium hydroxide / methanol / 1 h / 20 °C / pH 12 3.1: (1,2-bis(diphenylphosphanyl)ethane)dichloridopalladium(II); lithium triethylborohydride / tetrahydrofuran / 2 h / 0 - 20 °C / Inert atmosphere 4.1: phosphorus tribromide / tetrahydrofuran / 3 h / 0 °C / Inert atmosphere 5.1: potassium tert-butylate / tetrahydrofuran; N,N-dimethyl-formamide / 1 h / -20 °C 6.1: (1,2-bis(diphenylphosphanyl)ethane)dichloridopalladium(II); lithium triethylborohydride / tetrahydrofuran / 4 h / 0 °C / Inert atmosphere 7.1: ammonium cerium (IV) nitrate / water; acetonitrile; dichloromethane / 0.75 h / 0 °C View Scheme |
farnesyl bromide
menaquinone-7
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1.1: potassium tert-butylate / tetrahydrofuran; N,N-dimethyl-formamide / 2.67 h / -78 °C 1.2: -78 - 20 °C 2.1: sodium hydroxide; water / methanol / 1 h / 20 °C / pH 12 3.1: phosphorus tribromide / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere; Cooling with acetone-dry ice 4.1: sodium hexamethyldisilazane / tetrahydrofuran; N,N-dimethyl-formamide / 0.5 h / -20 - 0 °C / Inert atmosphere; Cooling with acetone-dry ice 5.1: (1,2-bis(diphenylphosphino)ethane)palladium(II) chloride / tetrahydrofuran / 0.08 h / 0 °C / Cooling with acetone-dry ice; Inert atmosphere 5.2: 4.5 h / 0 °C / Inert atmosphere 6.1: ammonium cerium (IV) nitrate / water; dichloromethane; acetonitrile / 0.25 h / 0 °C View Scheme | |
Multi-step reaction with 7 steps 1.1: potassium tert-butylate / tetrahydrofuran; N,N-dimethyl-formamide / 2.67 h / -78 °C 1.2: -78 - 20 °C 2.1: sodium hydroxide; water / methanol / 1 h / 20 °C / pH 12 3.1: (1,2-bis(diphenylphosphino)ethane)palladium(II) chloride; lithium triethylborohydride / tetrahydrofuran / 1.17 h / 0 °C / Inert atmosphere 4.1: phosphorus tribromide / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere; Cooling with acetone-dry ice 5.1: sodium hexamethyldisilazane / tetrahydrofuran; N,N-dimethyl-formamide / 0.83 h / -20 °C / Inert atmosphere; Cooling with acetone-dry ice 6.1: (1,2-bis(diphenylphosphino)ethane)palladium(II) chloride / tetrahydrofuran / 0.08 h / Inert atmosphere; Cooling with acetone-dry ice 6.2: 5 h / 0 °C / Inert atmosphere 7.1: ammonium cerium (IV) nitrate / water; dichloromethane; acetonitrile / 0.25 h / 0 °C View Scheme | |
Multi-step reaction with 8 steps 1.1: N,N-dimethyl-formamide / 18 h / 20 °C / Darkness 2.1: n-butyllithium / tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide / 1.5 h / -78 °C 2.2: -78 - 0 °C 3.1: sodium methylate / methanol / 2 h / 20 °C / pH 12 4.1: (1,2-bis(diphenylphosphanyl)ethane)dichloridopalladium(II); lithium triethylborohydride / tetrahydrofuran / 0 - 20 °C / Inert atmosphere 5.1: phosphorus tribromide / tetrahydrofuran / 3 h / 0 °C / Inert atmosphere 6.1: potassium tert-butylate / tetrahydrofuran; N,N-dimethyl-formamide / -20 °C 7.1: (1,2-bis(diphenylphosphanyl)ethane)dichloridopalladium(II); lithium triethylborohydride / tetrahydrofuran / 0 - 20 °C / Inert atmosphere 8.1: ammonium cerium (IV) nitrate / water; acetonitrile / 0.75 h / 0 °C View Scheme | |
Multi-step reaction with 7 steps 1.1: potassium tert-butylate / tetrahydrofuran; N,N-dimethyl-formamide / 2.5 h / -78 °C 1.2: -78 - 20 °C 2.1: sodium hydroxide / methanol / 1 h / 20 °C / pH 12 3.1: (1,2-bis(diphenylphosphanyl)ethane)dichloridopalladium(II); lithium triethylborohydride / tetrahydrofuran / 2 h / 0 - 20 °C / Inert atmosphere 4.1: phosphorus tribromide / tetrahydrofuran / 3 h / 0 °C / Inert atmosphere 5.1: potassium tert-butylate / tetrahydrofuran; N,N-dimethyl-formamide / 1 h / -20 °C 6.1: (1,2-bis(diphenylphosphanyl)ethane)dichloridopalladium(II); lithium triethylborohydride / tetrahydrofuran / 4 h / 0 °C / Inert atmosphere 7.1: ammonium cerium (IV) nitrate / water; acetonitrile; dichloromethane / 0.75 h / 0 °C View Scheme | |
Multi-step reaction with 8 steps 1.1: pyridine / N,N-dimethyl-formamide / 18 h / 20 °C / Darkness 2.1: n-butyllithium / tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide / 1.5 h / -78 °C 2.2: 5 h / -78 °C 3.1: sodium methylate; methanol / 2 h / 20 °C 4.1: (1,2-bis(diphenylphosphanyl)ethane)dichloridopalladium(II); lithium triethylborohydride / tetrahydrofuran / 2 h / 0 °C / Inert atmosphere 5.1: phosphorus tribromide / tetrahydrofuran / 3 h / 0 °C / Inert atmosphere 6.1: potassium tert-butylate / tetrahydrofuran; N,N-dimethyl-formamide / 1 h / -20 °C 7.1: (1,2-bis(diphenylphosphanyl)ethane)dichloridopalladium(II); lithium triethylborohydride / tetrahydrofuran / 4 h / 0 °C / Inert atmosphere 8.1: ammonium cerium (IV) nitrate / water; acetonitrile; dichloromethane / 0.75 h / 0 °C View Scheme |
C38H56O4S
menaquinone-7
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1.1: sodium hydroxide; water / methanol / 1 h / 20 °C / pH 12 2.1: phosphorus tribromide / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere; Cooling with acetone-dry ice 3.1: sodium hexamethyldisilazane / tetrahydrofuran; N,N-dimethyl-formamide / 0.5 h / -20 - 0 °C / Inert atmosphere; Cooling with acetone-dry ice 4.1: (1,2-bis(diphenylphosphino)ethane)palladium(II) chloride / tetrahydrofuran / 0.08 h / 0 °C / Cooling with acetone-dry ice; Inert atmosphere 4.2: 4.5 h / 0 °C / Inert atmosphere 5.1: ammonium cerium (IV) nitrate / water; dichloromethane; acetonitrile / 0.25 h / 0 °C View Scheme | |
Multi-step reaction with 6 steps 1.1: sodium hydroxide; water / methanol / 1 h / 20 °C / pH 12 2.1: (1,2-bis(diphenylphosphino)ethane)palladium(II) chloride; lithium triethylborohydride / tetrahydrofuran / 1.17 h / 0 °C / Inert atmosphere 3.1: phosphorus tribromide / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere; Cooling with acetone-dry ice 4.1: sodium hexamethyldisilazane / tetrahydrofuran; N,N-dimethyl-formamide / 0.83 h / -20 °C / Inert atmosphere; Cooling with acetone-dry ice 5.1: (1,2-bis(diphenylphosphino)ethane)palladium(II) chloride / tetrahydrofuran / 0.08 h / Inert atmosphere; Cooling with acetone-dry ice 5.2: 5 h / 0 °C / Inert atmosphere 6.1: ammonium cerium (IV) nitrate / water; dichloromethane; acetonitrile / 0.25 h / 0 °C View Scheme | |
Multi-step reaction with 6 steps 1: sodium hydroxide / methanol; water / 1 h / 20 °C / pH 12 2: (1,2-bis(diphenylphosphanyl)ethane)dichloridopalladium(II); lithium triethylborohydride / tetrahydrofuran / 0 - 20 °C / Inert atmosphere 3: phosphorus tribromide / tetrahydrofuran / 3 h / 0 °C / Inert atmosphere 4: potassium tert-butylate / tetrahydrofuran; N,N-dimethyl-formamide / -20 °C 5: (1,2-bis(diphenylphosphanyl)ethane)dichloridopalladium(II); lithium triethylborohydride / tetrahydrofuran / 0 - 20 °C / Inert atmosphere 6: ammonium cerium (IV) nitrate / water; acetonitrile / 0.75 h / 0 °C View Scheme | |
Multi-step reaction with 6 steps 1: sodium hydroxide / methanol / 1 h / 20 °C / pH 12 2: (1,2-bis(diphenylphosphanyl)ethane)dichloridopalladium(II); lithium triethylborohydride / tetrahydrofuran / 2 h / 0 - 20 °C / Inert atmosphere 3: phosphorus tribromide / tetrahydrofuran / 3 h / 0 °C / Inert atmosphere 4: potassium tert-butylate / tetrahydrofuran; N,N-dimethyl-formamide / 1 h / -20 °C 5: (1,2-bis(diphenylphosphanyl)ethane)dichloridopalladium(II); lithium triethylborohydride / tetrahydrofuran / 4 h / 0 °C / Inert atmosphere 6: ammonium cerium (IV) nitrate / water; acetonitrile; dichloromethane / 0.75 h / 0 °C View Scheme |
(2E,6E,10E,14E,18E)-3,7,11,15,19,23-hexamethyl-12-(phenylsulfonyl)tetracosa-2,6,10,14,18,22-hexaen-1-ol
menaquinone-7
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1.1: phosphorus tribromide / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere; Cooling with acetone-dry ice 2.1: sodium hexamethyldisilazane / tetrahydrofuran; N,N-dimethyl-formamide / 0.5 h / -20 - 0 °C / Inert atmosphere; Cooling with acetone-dry ice 3.1: (1,2-bis(diphenylphosphino)ethane)palladium(II) chloride / tetrahydrofuran / 0.08 h / 0 °C / Cooling with acetone-dry ice; Inert atmosphere 3.2: 4.5 h / 0 °C / Inert atmosphere 4.1: ammonium cerium (IV) nitrate / water; dichloromethane; acetonitrile / 0.25 h / 0 °C View Scheme | |
Multi-step reaction with 5 steps 1.1: (1,2-bis(diphenylphosphino)ethane)palladium(II) chloride; lithium triethylborohydride / tetrahydrofuran / 1.17 h / 0 °C / Inert atmosphere 2.1: phosphorus tribromide / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere; Cooling with acetone-dry ice 3.1: sodium hexamethyldisilazane / tetrahydrofuran; N,N-dimethyl-formamide / 0.83 h / -20 °C / Inert atmosphere; Cooling with acetone-dry ice 4.1: (1,2-bis(diphenylphosphino)ethane)palladium(II) chloride / tetrahydrofuran / 0.08 h / Inert atmosphere; Cooling with acetone-dry ice 4.2: 5 h / 0 °C / Inert atmosphere 5.1: ammonium cerium (IV) nitrate / water; dichloromethane; acetonitrile / 0.25 h / 0 °C View Scheme | |
Multi-step reaction with 5 steps 1: (1,2-bis(diphenylphosphanyl)ethane)dichloridopalladium(II); lithium triethylborohydride / tetrahydrofuran / 0 - 20 °C / Inert atmosphere 2: phosphorus tribromide / tetrahydrofuran / 3 h / 0 °C / Inert atmosphere 3: potassium tert-butylate / tetrahydrofuran; N,N-dimethyl-formamide / -20 °C 4: (1,2-bis(diphenylphosphanyl)ethane)dichloridopalladium(II); lithium triethylborohydride / tetrahydrofuran / 0 - 20 °C / Inert atmosphere 5: ammonium cerium (IV) nitrate / water; acetonitrile / 0.75 h / 0 °C View Scheme | |
Multi-step reaction with 5 steps 1: (1,2-bis(diphenylphosphanyl)ethane)dichloridopalladium(II); lithium triethylborohydride / tetrahydrofuran / 2 h / 0 - 20 °C / Inert atmosphere 2: phosphorus tribromide / tetrahydrofuran / 3 h / 0 °C / Inert atmosphere 3: potassium tert-butylate / tetrahydrofuran; N,N-dimethyl-formamide / 1 h / -20 °C 4: (1,2-bis(diphenylphosphanyl)ethane)dichloridopalladium(II); lithium triethylborohydride / tetrahydrofuran / 4 h / 0 °C / Inert atmosphere 5: ammonium cerium (IV) nitrate / water; acetonitrile; dichloromethane / 0.75 h / 0 °C View Scheme |
(2E,6E,10E)-12-bromo-3,7,11-trimethyl-2,6,10-dodecatrienyl acetate
menaquinone-7
Conditions | Yield |
---|---|
Multi-step reaction with 7 steps 1.1: N,N-dimethyl-formamide / 18 h / 20 °C / Darkness 2.1: potassium tert-butylate / tetrahydrofuran; N,N-dimethyl-formamide / 2.67 h / -78 °C 2.2: -78 - 20 °C 3.1: sodium hydroxide; water / methanol / 1 h / 20 °C / pH 12 4.1: phosphorus tribromide / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere; Cooling with acetone-dry ice 5.1: sodium hexamethyldisilazane / tetrahydrofuran; N,N-dimethyl-formamide / 0.5 h / -20 - 0 °C / Inert atmosphere; Cooling with acetone-dry ice 6.1: (1,2-bis(diphenylphosphino)ethane)palladium(II) chloride / tetrahydrofuran / 0.08 h / 0 °C / Cooling with acetone-dry ice; Inert atmosphere 6.2: 4.5 h / 0 °C / Inert atmosphere 7.1: ammonium cerium (IV) nitrate / water; dichloromethane; acetonitrile / 0.25 h / 0 °C View Scheme | |
Multi-step reaction with 8 steps 1.1: N,N-dimethyl-formamide / 18 h / 20 °C / Darkness 2.1: potassium tert-butylate / tetrahydrofuran; N,N-dimethyl-formamide / 2.67 h / -78 °C 2.2: -78 - 20 °C 3.1: sodium hydroxide; water / methanol / 1 h / 20 °C / pH 12 4.1: (1,2-bis(diphenylphosphino)ethane)palladium(II) chloride; lithium triethylborohydride / tetrahydrofuran / 1.17 h / 0 °C / Inert atmosphere 5.1: phosphorus tribromide / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere; Cooling with acetone-dry ice 6.1: sodium hexamethyldisilazane / tetrahydrofuran; N,N-dimethyl-formamide / 0.83 h / -20 °C / Inert atmosphere; Cooling with acetone-dry ice 7.1: (1,2-bis(diphenylphosphino)ethane)palladium(II) chloride / tetrahydrofuran / 0.08 h / Inert atmosphere; Cooling with acetone-dry ice 7.2: 5 h / 0 °C / Inert atmosphere 8.1: ammonium cerium (IV) nitrate / water; dichloromethane; acetonitrile / 0.25 h / 0 °C View Scheme | |
Multi-step reaction with 9 steps 1.1: n-butyllithium / tetrahydrofuran / 0.67 h / -78 °C / Inert atmosphere 1.2: Inert atmosphere 2.1: sodium methylate / methanol / 4 h / 0 °C 3.1: Dess-Martin periodane; water / dichloromethane; acetonitrile / 20 °C 4.1: hydrazine; potassium hydroxide / diethylene glycol / 4 h / 60 - 215 °C / Inert atmosphere; Reflux 5.1: triphenylphosphine; bromine / dichloromethane / 0 °C 6.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere 6.2: 12 h / Inert atmosphere 7.1: Dess-Martin periodane; water / dichloromethane; acetonitrile / 20 °C 8.1: hydrazine; potassium hydroxide / diethylene glycol / 4 h / 60 - 215 °C / Inert atmosphere; Reflux 9.1: ammonium cerium (IV) nitrate / water; acetonitrile / 4.08 h / 20 °C View Scheme |
(2E,6E,10E,14E,18E)-3,7,11,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaen-1-ol
menaquinone-7
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1.1: phosphorus tribromide / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere; Cooling with acetone-dry ice 2.1: sodium hexamethyldisilazane / tetrahydrofuran; N,N-dimethyl-formamide / 0.83 h / -20 °C / Inert atmosphere; Cooling with acetone-dry ice 3.1: (1,2-bis(diphenylphosphino)ethane)palladium(II) chloride / tetrahydrofuran / 0.08 h / Inert atmosphere; Cooling with acetone-dry ice 3.2: 5 h / 0 °C / Inert atmosphere 4.1: ammonium cerium (IV) nitrate / water; dichloromethane; acetonitrile / 0.25 h / 0 °C View Scheme | |
Multi-step reaction with 5 steps 1.1: triphenylphosphine; bromine / dichloromethane / 0 °C 2.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere 2.2: 12 h / Inert atmosphere 3.1: Dess-Martin periodane; water / dichloromethane; acetonitrile / 20 °C 4.1: hydrazine; potassium hydroxide / diethylene glycol / 4 h / 60 - 215 °C / Inert atmosphere; Reflux 5.1: ammonium cerium (IV) nitrate / water; acetonitrile / 4.08 h / 20 °C View Scheme | |
Multi-step reaction with 5 steps 1.1: triphenylphosphine; bromine / dichloromethane / 0 °C 2.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere 2.2: 12 h / Inert atmosphere 3.1: Dess-Martin periodane; water / dichloromethane; acetonitrile / 20 °C 4.1: hydrazine; potassium hydroxide / diethylene glycol / 4 h / 60 - 215 °C / Inert atmosphere; Reflux 5.1: ammonium cerium (IV) nitrate / acetonitrile / 4.08 h / 20 °C View Scheme | |
Multi-step reaction with 4 steps 1: phosphorus tribromide / tetrahydrofuran / 3 h / 0 °C / Inert atmosphere 2: potassium tert-butylate / tetrahydrofuran; N,N-dimethyl-formamide / -20 °C 3: (1,2-bis(diphenylphosphanyl)ethane)dichloridopalladium(II); lithium triethylborohydride / tetrahydrofuran / 0 - 20 °C / Inert atmosphere 4: ammonium cerium (IV) nitrate / water; acetonitrile / 0.75 h / 0 °C View Scheme | |
Multi-step reaction with 4 steps 1: phosphorus tribromide / tetrahydrofuran / 3 h / 0 °C / Inert atmosphere 2: potassium tert-butylate / tetrahydrofuran; N,N-dimethyl-formamide / 1 h / -20 °C 3: (1,2-bis(diphenylphosphanyl)ethane)dichloridopalladium(II); lithium triethylborohydride / tetrahydrofuran / 4 h / 0 °C / Inert atmosphere 4: ammonium cerium (IV) nitrate / water; acetonitrile; dichloromethane / 0.75 h / 0 °C View Scheme |
1-bromo-3,7,11,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene
menaquinone-7
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: sodium hexamethyldisilazane / tetrahydrofuran; N,N-dimethyl-formamide / 0.83 h / -20 °C / Inert atmosphere; Cooling with acetone-dry ice 2.1: (1,2-bis(diphenylphosphino)ethane)palladium(II) chloride / tetrahydrofuran / 0.08 h / Inert atmosphere; Cooling with acetone-dry ice 2.2: 5 h / 0 °C / Inert atmosphere 3.1: ammonium cerium (IV) nitrate / water; dichloromethane; acetonitrile / 0.25 h / 0 °C View Scheme | |
Multi-step reaction with 4 steps 1.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere 1.2: 12 h / Inert atmosphere 2.1: Dess-Martin periodane; water / dichloromethane; acetonitrile / 20 °C 3.1: hydrazine; potassium hydroxide / diethylene glycol / 4 h / 60 - 215 °C / Inert atmosphere; Reflux 4.1: ammonium cerium (IV) nitrate / water; acetonitrile / 4.08 h / 20 °C View Scheme | |
Multi-step reaction with 4 steps 1.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere 1.2: 12 h / Inert atmosphere 2.1: Dess-Martin periodane; water / dichloromethane; acetonitrile / 20 °C 3.1: hydrazine; potassium hydroxide / diethylene glycol / 4 h / 60 - 215 °C / Inert atmosphere; Reflux 4.1: ammonium cerium (IV) nitrate / acetonitrile / 4.08 h / 20 °C View Scheme | |
Multi-step reaction with 3 steps 1: potassium tert-butylate / tetrahydrofuran; N,N-dimethyl-formamide / -20 °C 2: (1,2-bis(diphenylphosphanyl)ethane)dichloridopalladium(II); lithium triethylborohydride / tetrahydrofuran / 0 - 20 °C / Inert atmosphere 3: ammonium cerium (IV) nitrate / water; acetonitrile / 0.75 h / 0 °C View Scheme | |
Multi-step reaction with 3 steps 1: potassium tert-butylate / tetrahydrofuran; N,N-dimethyl-formamide / 1 h / -20 °C 2: (1,2-bis(diphenylphosphanyl)ethane)dichloridopalladium(II); lithium triethylborohydride / tetrahydrofuran / 4 h / 0 °C / Inert atmosphere 3: ammonium cerium (IV) nitrate / water; acetonitrile; dichloromethane / 0.75 h / 0 °C View Scheme |
phenylsulfonyl hexaprenyl bromide
menaquinone-7
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: sodium hexamethyldisilazane / tetrahydrofuran; N,N-dimethyl-formamide / 0.5 h / -20 - 0 °C / Inert atmosphere; Cooling with acetone-dry ice 2.1: (1,2-bis(diphenylphosphino)ethane)palladium(II) chloride / tetrahydrofuran / 0.08 h / 0 °C / Cooling with acetone-dry ice; Inert atmosphere 2.2: 4.5 h / 0 °C / Inert atmosphere 3.1: ammonium cerium (IV) nitrate / water; dichloromethane; acetonitrile / 0.25 h / 0 °C View Scheme |
C62H82O6S2
menaquinone-7
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: (1,2-bis(diphenylphosphino)ethane)palladium(II) chloride / tetrahydrofuran / 0.08 h / 0 °C / Cooling with acetone-dry ice; Inert atmosphere 1.2: 4.5 h / 0 °C / Inert atmosphere 2.1: ammonium cerium (IV) nitrate / water; dichloromethane; acetonitrile / 0.25 h / 0 °C View Scheme |
C56H78O4S
menaquinone-7
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: (1,2-bis(diphenylphosphino)ethane)palladium(II) chloride / tetrahydrofuran / 0.08 h / Inert atmosphere; Cooling with acetone-dry ice 1.2: 5 h / 0 °C / Inert atmosphere 2.1: ammonium cerium (IV) nitrate / water; dichloromethane; acetonitrile / 0.25 h / 0 °C View Scheme |
(2E,6E,10E)-3,7,11-trimethyl-12-oxododeca-2,6,10-trien-1-yl acetate
menaquinone-7
Conditions | Yield |
---|---|
Multi-step reaction with 10 steps 1.1: sodium tetrahydroborate / methanol; tetrahydrofuran / 0.75 h / -10 °C 2.1: phosphorus tribromide / tetrahydrofuran / 3 h / 0 °C / Inert atmosphere 3.1: N,N-dimethyl-formamide / 18 h / 20 °C / Darkness 4.1: potassium tert-butylate / tetrahydrofuran; N,N-dimethyl-formamide / 2.67 h / -78 °C 4.2: -78 - 20 °C 5.1: sodium hydroxide; water / methanol / 1 h / 20 °C / pH 12 6.1: (1,2-bis(diphenylphosphino)ethane)palladium(II) chloride; lithium triethylborohydride / tetrahydrofuran / 1.17 h / 0 °C / Inert atmosphere 7.1: phosphorus tribromide / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere; Cooling with acetone-dry ice 8.1: sodium hexamethyldisilazane / tetrahydrofuran; N,N-dimethyl-formamide / 0.83 h / -20 °C / Inert atmosphere; Cooling with acetone-dry ice 9.1: (1,2-bis(diphenylphosphino)ethane)palladium(II) chloride / tetrahydrofuran / 0.08 h / Inert atmosphere; Cooling with acetone-dry ice 9.2: 5 h / 0 °C / Inert atmosphere 10.1: ammonium cerium (IV) nitrate / water; dichloromethane; acetonitrile / 0.25 h / 0 °C View Scheme | |
Multi-step reaction with 9 steps 1.1: sodium tetrahydroborate / methanol; tetrahydrofuran / 0.75 h / -10 °C 2.1: phosphorus tribromide / tetrahydrofuran / 3 h / 0 °C / Inert atmosphere 3.1: N,N-dimethyl-formamide / 18 h / 20 °C / Darkness 4.1: potassium tert-butylate / tetrahydrofuran; N,N-dimethyl-formamide / 2.67 h / -78 °C 4.2: -78 - 20 °C 5.1: sodium hydroxide; water / methanol / 1 h / 20 °C / pH 12 6.1: phosphorus tribromide / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere; Cooling with acetone-dry ice 7.1: sodium hexamethyldisilazane / tetrahydrofuran; N,N-dimethyl-formamide / 0.5 h / -20 - 0 °C / Inert atmosphere; Cooling with acetone-dry ice 8.1: (1,2-bis(diphenylphosphino)ethane)palladium(II) chloride / tetrahydrofuran / 0.08 h / 0 °C / Cooling with acetone-dry ice; Inert atmosphere 8.2: 4.5 h / 0 °C / Inert atmosphere 9.1: ammonium cerium (IV) nitrate / water; dichloromethane; acetonitrile / 0.25 h / 0 °C View Scheme | |
Multi-step reaction with 10 steps 1.1: sodium tetrahydroborate / methanol; tetrahydrofuran / 0.5 h / -10 °C 2.1: phosphorus tribromide / tetrahydrofuran / 3 h / 0 °C / Inert atmosphere 3.1: N,N-dimethyl-formamide / 18 h / 20 °C / Darkness 4.1: potassium tert-butylate / tetrahydrofuran; N,N-dimethyl-formamide / 2.5 h / -78 °C 4.2: -78 - 20 °C 5.1: sodium hydroxide / methanol; water / 1 h / 20 °C / pH 12 6.1: (1,2-bis(diphenylphosphanyl)ethane)dichloridopalladium(II); lithium triethylborohydride / tetrahydrofuran / 0 - 20 °C / Inert atmosphere 7.1: phosphorus tribromide / tetrahydrofuran / 3 h / 0 °C / Inert atmosphere 8.1: potassium tert-butylate / tetrahydrofuran; N,N-dimethyl-formamide / -20 °C 9.1: (1,2-bis(diphenylphosphanyl)ethane)dichloridopalladium(II); lithium triethylborohydride / tetrahydrofuran / 0 - 20 °C / Inert atmosphere 10.1: ammonium cerium (IV) nitrate / water; acetonitrile / 0.75 h / 0 °C View Scheme |
1,4-diethoxy-2-methyl-3-[(2E)-3-methyl-4-(phenylsulfonyl)-2-buten-1-yl]naphtalene
menaquinone-7
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: sodium hexamethyldisilazane / tetrahydrofuran; N,N-dimethyl-formamide / 0.5 h / -20 - 0 °C / Inert atmosphere; Cooling with acetone-dry ice 2.1: (1,2-bis(diphenylphosphino)ethane)palladium(II) chloride / tetrahydrofuran / 0.08 h / 0 °C / Cooling with acetone-dry ice; Inert atmosphere 2.2: 4.5 h / 0 °C / Inert atmosphere 3.1: ammonium cerium (IV) nitrate / water; dichloromethane; acetonitrile / 0.25 h / 0 °C View Scheme | |
Multi-step reaction with 3 steps 1.1: sodium hexamethyldisilazane / tetrahydrofuran; N,N-dimethyl-formamide / 0.83 h / -20 °C / Inert atmosphere; Cooling with acetone-dry ice 2.1: (1,2-bis(diphenylphosphino)ethane)palladium(II) chloride / tetrahydrofuran / 0.08 h / Inert atmosphere; Cooling with acetone-dry ice 2.2: 5 h / 0 °C / Inert atmosphere 3.1: ammonium cerium (IV) nitrate / water; dichloromethane; acetonitrile / 0.25 h / 0 °C View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 11 steps 1.1: pyridine / 12 h / 0 - 20 °C / Inert atmosphere 2.1: salicylic acid; selenium(IV) oxide; tert.-butylhydroperoxide / water; dichloromethane / 24 h / 0 - 20 °C 3.1: sodium tetrahydroborate / methanol; tetrahydrofuran / 0.75 h / -10 °C 4.1: phosphorus tribromide / tetrahydrofuran / 3 h / 0 °C / Inert atmosphere 5.1: N,N-dimethyl-formamide / 18 h / 20 °C / Darkness 6.1: potassium tert-butylate / tetrahydrofuran; N,N-dimethyl-formamide / 2.67 h / -78 °C 6.2: -78 - 20 °C 7.1: sodium hydroxide; water / methanol / 1 h / 20 °C / pH 12 8.1: phosphorus tribromide / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere; Cooling with acetone-dry ice 9.1: sodium hexamethyldisilazane / tetrahydrofuran; N,N-dimethyl-formamide / 0.5 h / -20 - 0 °C / Inert atmosphere; Cooling with acetone-dry ice 10.1: (1,2-bis(diphenylphosphino)ethane)palladium(II) chloride / tetrahydrofuran / 0.08 h / 0 °C / Cooling with acetone-dry ice; Inert atmosphere 10.2: 4.5 h / 0 °C / Inert atmosphere 11.1: ammonium cerium (IV) nitrate / water; dichloromethane; acetonitrile / 0.25 h / 0 °C View Scheme | |
Multi-step reaction with 12 steps 1.1: pyridine / 12 h / 0 - 20 °C / Inert atmosphere 2.1: salicylic acid; selenium(IV) oxide; tert.-butylhydroperoxide / water; dichloromethane / 24 h / 0 - 20 °C 3.1: sodium tetrahydroborate / methanol; tetrahydrofuran / 0.75 h / -10 °C 4.1: phosphorus tribromide / tetrahydrofuran / 3 h / 0 °C / Inert atmosphere 5.1: N,N-dimethyl-formamide / 18 h / 20 °C / Darkness 6.1: potassium tert-butylate / tetrahydrofuran; N,N-dimethyl-formamide / 2.67 h / -78 °C 6.2: -78 - 20 °C 7.1: sodium hydroxide; water / methanol / 1 h / 20 °C / pH 12 8.1: (1,2-bis(diphenylphosphino)ethane)palladium(II) chloride; lithium triethylborohydride / tetrahydrofuran / 1.17 h / 0 °C / Inert atmosphere 9.1: phosphorus tribromide / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere; Cooling with acetone-dry ice 10.1: sodium hexamethyldisilazane / tetrahydrofuran; N,N-dimethyl-formamide / 0.83 h / -20 °C / Inert atmosphere; Cooling with acetone-dry ice 11.1: (1,2-bis(diphenylphosphino)ethane)palladium(II) chloride / tetrahydrofuran / 0.08 h / Inert atmosphere; Cooling with acetone-dry ice 11.2: 5 h / 0 °C / Inert atmosphere 12.1: ammonium cerium (IV) nitrate / water; dichloromethane; acetonitrile / 0.25 h / 0 °C View Scheme | |
Multi-step reaction with 7 steps 1.1: phosphorus tribromide / tetrahydrofuran / 3 h / 0 °C 2.1: potassium tert-butylate / tetrahydrofuran; N,N-dimethyl-formamide / 2.67 h / -78 °C 2.2: -78 - 20 °C 3.1: sodium hydroxide; water / methanol / 1 h / 20 °C / pH 12 4.1: phosphorus tribromide / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere; Cooling with acetone-dry ice 5.1: sodium hexamethyldisilazane / tetrahydrofuran; N,N-dimethyl-formamide / 0.5 h / -20 - 0 °C / Inert atmosphere; Cooling with acetone-dry ice 6.1: (1,2-bis(diphenylphosphino)ethane)palladium(II) chloride / tetrahydrofuran / 0.08 h / 0 °C / Cooling with acetone-dry ice; Inert atmosphere 6.2: 4.5 h / 0 °C / Inert atmosphere 7.1: ammonium cerium (IV) nitrate / water; dichloromethane; acetonitrile / 0.25 h / 0 °C View Scheme |
1,4-dimethoxy-2-methylnaphthalene
menaquinone-7
Conditions | Yield |
---|---|
Multi-step reaction with 10 steps 1.1: titanium tetrachloride / dichloromethane / 2.17 h / -45 - 0 °C / Inert atmosphere 2.1: potassium tert-butylate / tetrahydrofuran / 0.5 h / 0 °C 2.2: 2.25 h / 0 °C 2.3: 0.67 h / Reflux 3.1: sodium hydride / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere 3.2: 14 h / Inert atmosphere 4.1: diisobutylaluminium hydride / tetrahydrofuran / 6 h / Inert atmosphere 5.1: dipyridinium dichromate / N,N-dimethyl-formamide / 20 °C / Inert atmosphere 6.1: iodine / chloroform / 6 h / 20 °C 7.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere 7.2: 12 h / Inert atmosphere 8.1: Dess-Martin periodane; water / dichloromethane; acetonitrile / 20 °C 9.1: hydrazine; potassium hydroxide / diethylene glycol / 4 h / 60 - 215 °C / Inert atmosphere; Reflux 10.1: ammonium cerium (IV) nitrate / water; acetonitrile / 4.08 h / 20 °C View Scheme | |
Multi-step reaction with 10 steps 1.1: titanium tetrachloride / dichloromethane / 2.17 h / -45 - 0 °C / Inert atmosphere 2.1: potassium tert-butylate / tetrahydrofuran / 0.5 h / 0 °C 2.2: 2.25 h / 0 °C 2.3: 0.67 h / Reflux 3.1: sodium hydride / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere 3.2: 14 h / Inert atmosphere 4.1: diisobutylaluminium hydride / tetrahydrofuran / 6 h / Inert atmosphere 5.1: dipyridinium dichromate / N,N-dimethyl-formamide / 20 °C / Inert atmosphere 6.1: iodine / chloroform / 6 h / 20 °C 7.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere 7.2: 12 h / Inert atmosphere 8.1: Dess-Martin periodane; water / dichloromethane; acetonitrile / 20 °C 9.1: hydrazine; potassium hydroxide / diethylene glycol / 4 h / 60 - 215 °C / Inert atmosphere; Reflux 10.1: ammonium cerium (IV) nitrate / acetonitrile / 4.08 h / 20 °C View Scheme | |
Multi-step reaction with 4 steps 1: tin(IV) chloride / 1,2-dichloro-ethane / 20 - 80 °C 2: potassium tert-butylate / tetrahydrofuran; N,N-dimethyl-formamide / -20 °C 3: (1,2-bis(diphenylphosphanyl)ethane)dichloridopalladium(II); lithium triethylborohydride / tetrahydrofuran / 0 - 20 °C / Inert atmosphere 4: ammonium cerium (IV) nitrate / water; acetonitrile / 0.75 h / 0 °C View Scheme | |
Multi-step reaction with 4 steps 1: tin(IV) chloride / 1,2-dichloro-ethane / 5 h / 80 °C 2: potassium tert-butylate / tetrahydrofuran; N,N-dimethyl-formamide / 1 h / -20 °C 3: (1,2-bis(diphenylphosphanyl)ethane)dichloridopalladium(II); lithium triethylborohydride / tetrahydrofuran / 4 h / 0 °C / Inert atmosphere 4: ammonium cerium (IV) nitrate / water; acetonitrile; dichloromethane / 0.75 h / 0 °C View Scheme |
1,4-dimethoxynaphthalene-3-methyl-2-carboxaldehyde
menaquinone-7
Conditions | Yield |
---|---|
Multi-step reaction with 9 steps 1.1: potassium tert-butylate / tetrahydrofuran / 0.5 h / 0 °C 1.2: 2.25 h / 0 °C 1.3: 0.67 h / Reflux 2.1: sodium hydride / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere 2.2: 14 h / Inert atmosphere 3.1: diisobutylaluminium hydride / tetrahydrofuran / 6 h / Inert atmosphere 4.1: dipyridinium dichromate / N,N-dimethyl-formamide / 20 °C / Inert atmosphere 5.1: iodine / chloroform / 6 h / 20 °C 6.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere 6.2: 12 h / Inert atmosphere 7.1: Dess-Martin periodane; water / dichloromethane; acetonitrile / 20 °C 8.1: hydrazine; potassium hydroxide / diethylene glycol / 4 h / 60 - 215 °C / Inert atmosphere; Reflux 9.1: ammonium cerium (IV) nitrate / water; acetonitrile / 4.08 h / 20 °C View Scheme | |
Multi-step reaction with 9 steps 1.1: potassium tert-butylate / tetrahydrofuran / 0.5 h / 0 °C 1.2: 2.25 h / 0 °C 1.3: 0.67 h / Reflux 2.1: sodium hydride / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere 2.2: 14 h / Inert atmosphere 3.1: diisobutylaluminium hydride / tetrahydrofuran / 6 h / Inert atmosphere 4.1: dipyridinium dichromate / N,N-dimethyl-formamide / 20 °C / Inert atmosphere 5.1: iodine / chloroform / 6 h / 20 °C 6.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere 6.2: 12 h / Inert atmosphere 7.1: Dess-Martin periodane; water / dichloromethane; acetonitrile / 20 °C 8.1: hydrazine; potassium hydroxide / diethylene glycol / 4 h / 60 - 215 °C / Inert atmosphere; Reflux 9.1: ammonium cerium (IV) nitrate / acetonitrile / 4.08 h / 20 °C View Scheme |
(1,4-dimethoxy-3-methylnaphthalen-2-yl)acetaldehyde
menaquinone-7
Conditions | Yield |
---|---|
Multi-step reaction with 8 steps 1.1: sodium hydride / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere 1.2: 14 h / Inert atmosphere 2.1: diisobutylaluminium hydride / tetrahydrofuran / 6 h / Inert atmosphere 3.1: dipyridinium dichromate / N,N-dimethyl-formamide / 20 °C / Inert atmosphere 4.1: iodine / chloroform / 6 h / 20 °C 5.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere 5.2: 12 h / Inert atmosphere 6.1: Dess-Martin periodane; water / dichloromethane; acetonitrile / 20 °C 7.1: hydrazine; potassium hydroxide / diethylene glycol / 4 h / 60 - 215 °C / Inert atmosphere; Reflux 8.1: ammonium cerium (IV) nitrate / water; acetonitrile / 4.08 h / 20 °C View Scheme | |
Multi-step reaction with 8 steps 1.1: sodium hydride / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere 1.2: 14 h / Inert atmosphere 2.1: diisobutylaluminium hydride / tetrahydrofuran / 6 h / Inert atmosphere 3.1: dipyridinium dichromate / N,N-dimethyl-formamide / 20 °C / Inert atmosphere 4.1: iodine / chloroform / 6 h / 20 °C 5.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere 5.2: 12 h / Inert atmosphere 6.1: Dess-Martin periodane; water / dichloromethane; acetonitrile / 20 °C 7.1: hydrazine; potassium hydroxide / diethylene glycol / 4 h / 60 - 215 °C / Inert atmosphere; Reflux 8.1: ammonium cerium (IV) nitrate / acetonitrile / 4.08 h / 20 °C View Scheme |
menaquinone-7
Conditions | Yield |
---|---|
Multi-step reaction with 7 steps 1.1: diisobutylaluminium hydride / tetrahydrofuran / 6 h / Inert atmosphere 2.1: dipyridinium dichromate / N,N-dimethyl-formamide / 20 °C / Inert atmosphere 3.1: iodine / chloroform / 6 h / 20 °C 4.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere 4.2: 12 h / Inert atmosphere 5.1: Dess-Martin periodane; water / dichloromethane; acetonitrile / 20 °C 6.1: hydrazine; potassium hydroxide / diethylene glycol / 4 h / 60 - 215 °C / Inert atmosphere; Reflux 7.1: ammonium cerium (IV) nitrate / water; acetonitrile / 4.08 h / 20 °C View Scheme | |
Multi-step reaction with 7 steps 1.1: diisobutylaluminium hydride / tetrahydrofuran / 6 h / Inert atmosphere 2.1: dipyridinium dichromate / N,N-dimethyl-formamide / 20 °C / Inert atmosphere 3.1: iodine / chloroform / 6 h / 20 °C 4.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere 4.2: 12 h / Inert atmosphere 5.1: Dess-Martin periodane; water / dichloromethane; acetonitrile / 20 °C 6.1: hydrazine; potassium hydroxide / diethylene glycol / 4 h / 60 - 215 °C / Inert atmosphere; Reflux 7.1: ammonium cerium (IV) nitrate / acetonitrile / 4.08 h / 20 °C View Scheme |
menaquinone-7
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere 1.2: 12 h / Inert atmosphere 2.1: Dess-Martin periodane; water / dichloromethane; acetonitrile / 20 °C 3.1: hydrazine; potassium hydroxide / diethylene glycol / 4 h / 60 - 215 °C / Inert atmosphere; Reflux 4.1: ammonium cerium (IV) nitrate / water; acetonitrile / 4.08 h / 20 °C View Scheme | |
Multi-step reaction with 4 steps 1.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere 1.2: 12 h / Inert atmosphere 2.1: Dess-Martin periodane; water / dichloromethane; acetonitrile / 20 °C 3.1: hydrazine; potassium hydroxide / diethylene glycol / 4 h / 60 - 215 °C / Inert atmosphere; Reflux 4.1: ammonium cerium (IV) nitrate / acetonitrile / 4.08 h / 20 °C View Scheme |
(E)-4-(1,4-dimethoxy-3-methylnaphthalen-2-yl)-2-methylbut-2-en-1-ol
menaquinone-7
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1.1: dipyridinium dichromate / N,N-dimethyl-formamide / 20 °C / Inert atmosphere 2.1: iodine / chloroform / 6 h / 20 °C 3.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere 3.2: 12 h / Inert atmosphere 4.1: Dess-Martin periodane; water / dichloromethane; acetonitrile / 20 °C 5.1: hydrazine; potassium hydroxide / diethylene glycol / 4 h / 60 - 215 °C / Inert atmosphere; Reflux 6.1: ammonium cerium (IV) nitrate / water; acetonitrile / 4.08 h / 20 °C View Scheme | |
Multi-step reaction with 6 steps 1.1: dipyridinium dichromate / N,N-dimethyl-formamide / 20 °C / Inert atmosphere 2.1: iodine / chloroform / 6 h / 20 °C 3.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere 3.2: 12 h / Inert atmosphere 4.1: Dess-Martin periodane; water / dichloromethane; acetonitrile / 20 °C 5.1: hydrazine; potassium hydroxide / diethylene glycol / 4 h / 60 - 215 °C / Inert atmosphere; Reflux 6.1: ammonium cerium (IV) nitrate / acetonitrile / 4.08 h / 20 °C View Scheme |
4-(1,4-dimethoxy-3-methylnaphthalen-2-yl)-2-methylbut-2-enal
menaquinone-7
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1.1: iodine / chloroform / 6 h / 20 °C 2.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere 2.2: 12 h / Inert atmosphere 3.1: Dess-Martin periodane; water / dichloromethane; acetonitrile / 20 °C 4.1: hydrazine; potassium hydroxide / diethylene glycol / 4 h / 60 - 215 °C / Inert atmosphere; Reflux 5.1: ammonium cerium (IV) nitrate / water; acetonitrile / 4.08 h / 20 °C View Scheme | |
Multi-step reaction with 5 steps 1.1: iodine / chloroform / 6 h / 20 °C 2.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere 2.2: 12 h / Inert atmosphere 3.1: Dess-Martin periodane; water / dichloromethane; acetonitrile / 20 °C 4.1: hydrazine; potassium hydroxide / diethylene glycol / 4 h / 60 - 215 °C / Inert atmosphere; Reflux 5.1: ammonium cerium (IV) nitrate / acetonitrile / 4.08 h / 20 °C View Scheme |
menaquinone-7
Conditions | Yield |
---|---|
Multi-step reaction with 9 steps 1.1: n-butyllithium / tetrahydrofuran / 0.67 h / -78 °C / Inert atmosphere 1.2: Inert atmosphere 2.1: sodium methylate / methanol / 4 h / 0 °C 3.1: Dess-Martin periodane; water / dichloromethane; acetonitrile / 20 °C 4.1: hydrazine; potassium hydroxide / diethylene glycol / 4 h / 60 - 215 °C / Inert atmosphere; Reflux 5.1: triphenylphosphine; bromine / dichloromethane / 0 °C 6.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere 6.2: 12 h / Inert atmosphere 7.1: Dess-Martin periodane; water / dichloromethane; acetonitrile / 20 °C 8.1: hydrazine; potassium hydroxide / diethylene glycol / 4 h / 60 - 215 °C / Inert atmosphere; Reflux 9.1: ammonium cerium (IV) nitrate / water; acetonitrile / 4.08 h / 20 °C View Scheme | |
Multi-step reaction with 9 steps 1.1: n-butyllithium / tetrahydrofuran / 0.67 h / -78 °C / Inert atmosphere 2.1: sodium methylate / methanol / 4 h / 0 °C 3.1: Dess-Martin periodane; water / dichloromethane; acetonitrile / 20 °C 4.1: hydrazine; potassium hydroxide / diethylene glycol / 4 h / 60 - 215 °C / Inert atmosphere; Reflux 5.1: triphenylphosphine; bromine / dichloromethane / 0 °C 6.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere 6.2: 12 h / Inert atmosphere 7.1: Dess-Martin periodane; water / dichloromethane; acetonitrile / 20 °C 8.1: hydrazine; potassium hydroxide / diethylene glycol / 4 h / 60 - 215 °C / Inert atmosphere; Reflux 9.1: ammonium cerium (IV) nitrate / acetonitrile / 4.08 h / 20 °C View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 12 steps 1.1: water; sodium dithionite / ethyl acetate; water / Inert atmosphere 2.1: potassium carbonate / acetone / 6 h / Reflux 3.1: titanium tetrachloride / dichloromethane / 2.17 h / -45 - 0 °C / Inert atmosphere 4.1: potassium tert-butylate / tetrahydrofuran / 0.5 h / 0 °C 4.2: 2.25 h / 0 °C 4.3: 0.67 h / Reflux 5.1: sodium hydride / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere 5.2: 14 h / Inert atmosphere 6.1: diisobutylaluminium hydride / tetrahydrofuran / 6 h / Inert atmosphere 7.1: dipyridinium dichromate / N,N-dimethyl-formamide / 20 °C / Inert atmosphere 8.1: iodine / chloroform / 6 h / 20 °C 9.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere 9.2: 12 h / Inert atmosphere 10.1: Dess-Martin periodane; water / dichloromethane; acetonitrile / 20 °C 11.1: hydrazine; potassium hydroxide / diethylene glycol / 4 h / 60 - 215 °C / Inert atmosphere; Reflux 12.1: ammonium cerium (IV) nitrate / water; acetonitrile / 4.08 h / 20 °C View Scheme | |
Multi-step reaction with 12 steps 1.1: water; sodium dithionite / ethyl acetate / Inert atmosphere 2.1: potassium carbonate / acetone / 6 h / Reflux 3.1: titanium tetrachloride / dichloromethane / 2.17 h / -45 - 0 °C / Inert atmosphere 4.1: potassium tert-butylate / tetrahydrofuran / 0.5 h / 0 °C 4.2: 2.25 h / 0 °C 4.3: 0.67 h / Reflux 5.1: sodium hydride / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere 5.2: 14 h / Inert atmosphere 6.1: diisobutylaluminium hydride / tetrahydrofuran / 6 h / Inert atmosphere 7.1: dipyridinium dichromate / N,N-dimethyl-formamide / 20 °C / Inert atmosphere 8.1: iodine / chloroform / 6 h / 20 °C 9.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere 9.2: 12 h / Inert atmosphere 10.1: Dess-Martin periodane; water / dichloromethane; acetonitrile / 20 °C 11.1: hydrazine; potassium hydroxide / diethylene glycol / 4 h / 60 - 215 °C / Inert atmosphere; Reflux 12.1: ammonium cerium (IV) nitrate / acetonitrile / 4.08 h / 20 °C View Scheme | |
Multi-step reaction with 6 steps 1: sodium dithionite / ethyl acetate; water / 0.33 h / 20 °C / Inert atmosphere 2: potassium carbonate / acetone / 6 h / Reflux 3: tin(IV) chloride / 1,2-dichloro-ethane / 20 - 80 °C 4: potassium tert-butylate / tetrahydrofuran; N,N-dimethyl-formamide / -20 °C 5: (1,2-bis(diphenylphosphanyl)ethane)dichloridopalladium(II); lithium triethylborohydride / tetrahydrofuran / 0 - 20 °C / Inert atmosphere 6: ammonium cerium (IV) nitrate / water; acetonitrile / 0.75 h / 0 °C View Scheme | |
Multi-step reaction with 6 steps 1: sodium dithionite / ethyl acetate; water / 0.33 h / 20 °C / Inert atmosphere 2: potassium carbonate / acetone / 6 h / Reflux 3: tin(IV) chloride / 1,2-dichloro-ethane / 5 h / 80 °C 4: potassium tert-butylate / tetrahydrofuran; N,N-dimethyl-formamide / 1 h / -20 °C 5: (1,2-bis(diphenylphosphanyl)ethane)dichloridopalladium(II); lithium triethylborohydride / tetrahydrofuran / 4 h / 0 °C / Inert atmosphere 6: ammonium cerium (IV) nitrate / water; acetonitrile; dichloromethane / 0.75 h / 0 °C View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 10 steps 1.1: iodine / chloroform / 6 h / 20 °C 2.1: n-butyllithium / tetrahydrofuran / 0.67 h / -78 °C / Inert atmosphere 2.2: Inert atmosphere 3.1: sodium methylate / methanol / 4 h / 0 °C 4.1: Dess-Martin periodane; water / dichloromethane; acetonitrile / 20 °C 5.1: hydrazine; potassium hydroxide / diethylene glycol / 4 h / 60 - 215 °C / Inert atmosphere; Reflux 6.1: triphenylphosphine; bromine / dichloromethane / 0 °C 7.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere 7.2: 12 h / Inert atmosphere 8.1: Dess-Martin periodane; water / dichloromethane; acetonitrile / 20 °C 9.1: hydrazine; potassium hydroxide / diethylene glycol / 4 h / 60 - 215 °C / Inert atmosphere; Reflux 10.1: ammonium cerium (IV) nitrate / water; acetonitrile / 4.08 h / 20 °C View Scheme | |
Multi-step reaction with 10 steps 1.1: iodine / chloroform / 6 h / 20 °C 2.1: n-butyllithium / tetrahydrofuran / 0.67 h / -78 °C / Inert atmosphere 3.1: sodium methylate / methanol / 4 h / 0 °C 4.1: Dess-Martin periodane; water / dichloromethane; acetonitrile / 20 °C 5.1: hydrazine; potassium hydroxide / diethylene glycol / 4 h / 60 - 215 °C / Inert atmosphere; Reflux 6.1: triphenylphosphine; bromine / dichloromethane / 0 °C 7.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere 7.2: 12 h / Inert atmosphere 8.1: Dess-Martin periodane; water / dichloromethane; acetonitrile / 20 °C 9.1: hydrazine; potassium hydroxide / diethylene glycol / 4 h / 60 - 215 °C / Inert atmosphere; Reflux 10.1: ammonium cerium (IV) nitrate / acetonitrile / 4.08 h / 20 °C View Scheme |
menaquinone-7
Conditions | Yield |
---|---|
Multi-step reaction with 8 steps 1.1: sodium methylate / methanol / 4 h / 0 °C 2.1: Dess-Martin periodane; water / dichloromethane; acetonitrile / 20 °C 3.1: hydrazine; potassium hydroxide / diethylene glycol / 4 h / 60 - 215 °C / Inert atmosphere; Reflux 4.1: triphenylphosphine; bromine / dichloromethane / 0 °C 5.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere 5.2: 12 h / Inert atmosphere 6.1: Dess-Martin periodane; water / dichloromethane; acetonitrile / 20 °C 7.1: hydrazine; potassium hydroxide / diethylene glycol / 4 h / 60 - 215 °C / Inert atmosphere; Reflux 8.1: ammonium cerium (IV) nitrate / water; acetonitrile / 4.08 h / 20 °C View Scheme | |
Multi-step reaction with 8 steps 1.1: sodium methylate / methanol / 4 h / 0 °C 2.1: Dess-Martin periodane; water / dichloromethane; acetonitrile / 20 °C 3.1: hydrazine; potassium hydroxide / diethylene glycol / 4 h / 60 - 215 °C / Inert atmosphere; Reflux 4.1: triphenylphosphine; bromine / dichloromethane / 0 °C 5.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere 5.2: 12 h / Inert atmosphere 6.1: Dess-Martin periodane; water / dichloromethane; acetonitrile / 20 °C 7.1: hydrazine; potassium hydroxide / diethylene glycol / 4 h / 60 - 215 °C / Inert atmosphere; Reflux 8.1: ammonium cerium (IV) nitrate / acetonitrile / 4.08 h / 20 °C View Scheme |
menaquinone-7
propionic acid anhydride
2-((2E,6E,10E,14E,18E,22E)-3,7,11,15,19,23,27-heptamethyloctacosa-2,6,10,14,18,22,26-heptaen-1-yl)-3-methylnaphthalene-1,4-diyl dipropionate
Conditions | Yield |
---|---|
With sodium acetate; zinc at 130℃; for 0.5h; | 66% |
With sodium acetate; zinc at 130℃; for 0.5h; | 66% |
menaquinone-7
benzoic acid anhydride
2-((2E,6E,10E,14E,18E,22E)-3,7,11,15,19,23,27-heptamethyl-octacosa-2,6,10,14,18,22,26-heptaen-1-yl)-3-methylnaphthalene-1,4-diyl dibenzoate
Conditions | Yield |
---|---|
With sodium acetate; zinc at 140℃; for 1h; | 50% |
Stage #1: menaquinone-7; benzoic acid anhydride With sodium acetate; zinc at 140℃; for 1h; Stage #2: With diethylamine In tetrahydrofuran at 20℃; for 1h; | 50% |
menaquinone-7
4-(trifluoromethyl)benzoic anhydride
2-((2E,6E,10E,14E,18E,22E)-3,7,11,15,19,23,27-heptamethyloctacosa-2,6,10,14,18,22,26-heptaen-1-yl)-3-methylnaphthalene-1,4-diyl bis(4-(trifluoromethyl)benzoate)
Conditions | Yield |
---|---|
With sodium acetate; zinc at 170℃; for 23h; | 11% |
Stage #1: menaquinone-7; 4-(trifluoromethyl)benzoic anhydride With sodium acetate; zinc at 170℃; for 23h; Stage #2: With diethylamine In tetrahydrofuran at 20℃; for 1h; | 11% |
menaquinone-7
acetic anhydride
1,4-diacetoxy-2-methyl-3-(3,7,11,15,19,23,27-heptamethyl-octacosaheptaen-(2t,6t,10t,14t,18t,22t,26)-yl)-naphthalene
Conditions | Yield |
---|---|
With sodium acetate; zinc | |
With sodium acetate; zinc |
menaquinone-7
3-((2E,6E,10E,14E,18E,22E)-3,7,11,15,19,23,27-heptamethyloctacosa-2,6,10,14,18,22,26-heptaen-1-yl)-4-hydroxy-2-methylnaphthalen-1-yl benzoate
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: sodium acetate; zinc / 0.5 h / 130 °C 2: lithium hydroxide; water / tetrahydrofuran / 20 h / 50 °C View Scheme | |
Multi-step reaction with 2 steps 1: sodium acetate; zinc / 1 h / 140 °C 2: lithium hydroxide; water / tetrahydrofuran / 20 h / 50 °C View Scheme | |
Multi-step reaction with 2 steps 1.1: sodium acetate; zinc / 1 h / 140 °C 1.2: 1 h / 20 °C 2.1: lithium hydroxide monohydrate; water / tetrahydrofuran / 20 h / 50 °C View Scheme |
menaquinone-7
4-((diethoxyphosphoryl)oxy)-2-((2E,6E, 10E,14E,18E,22E)-3,7,11,15,19,23,27-heptamethyloctacosa-2,6,10,14,18,22,26-heptaen-1-yl)-3-methylnaphthalen-1-yl benzoate
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: sodium acetate; zinc / 1 h / 140 °C 2: lithium hydroxide; water / tetrahydrofuran / 20 h / 50 °C 3: triethylamine / dichloromethane / 20 h / 0 - 20 °C View Scheme | |
Multi-step reaction with 3 steps 1.1: sodium acetate; zinc / 1 h / 140 °C 1.2: 1 h / 20 °C 2.1: lithium hydroxide monohydrate; water / tetrahydrofuran / 20 h / 50 °C 3.1: triethylamine / dichloromethane / 20 h / 0 - 20 °C View Scheme |
menaquinone-7
4-((diethoxyphosphoryl)oxy)-3-((2E,6E,10E,14E,18E,22E)-3,7,11,15,19,23,27-heptamethyloctacosa-2,6,10,14,18,22,26-heptaen-1-yl)-2-methylnaphthalen-1-yl benzoate
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: sodium acetate; zinc / 0.5 h / 130 °C 2: lithium hydroxide; water / tetrahydrofuran / 20 h / 50 °C 3: triethylamine / dichloromethane / 20 h / 0 - 20 °C View Scheme | |
Multi-step reaction with 3 steps 1: sodium acetate; zinc / 1 h / 140 °C 2: lithium hydroxide; water / tetrahydrofuran / 20 h / 50 °C 3: triethylamine / dichloromethane / 20 h / 0 - 20 °C View Scheme | |
Multi-step reaction with 3 steps 1.1: sodium acetate; zinc / 1 h / 140 °C 1.2: 1 h / 20 °C 2.1: lithium hydroxide monohydrate; water / tetrahydrofuran / 20 h / 50 °C 3.1: triethylamine / dichloromethane / 20 h / 0 - 20 °C View Scheme |
menaquinone-7
4-(((tert-butoxycarbonyl)glycyl)oxy)-2-((2E,6E,10E,14E,18E,22E)-3,7,11,15,19,23,27-heptamethyloctacosa-2,6,10,14,18,22,26-heptaen-1-yl)-3-methylnaphthalen-1-yl benzoate
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: sodium acetate; zinc / 1 h / 140 °C 2: lithium hydroxide; water / tetrahydrofuran / 20 h / 50 °C 3: dmap; dicyclohexyl-carbodiimide / dichloromethane / 20 h / 20 °C View Scheme | |
Multi-step reaction with 3 steps 1.1: sodium acetate; zinc / 1 h / 140 °C 1.2: 1 h / 20 °C 2.1: lithium hydroxide monohydrate; water / tetrahydrofuran / 20 h / 50 °C 3.1: dmap; dicyclohexyl-carbodiimide / dichloromethane / 20 h / 20 °C View Scheme |
menaquinone-7
4-(((tert-butoxycarbonyl)-L-valyl)oxy)-2-((2E,6E,10E,14E,18E,22E)-3,7,11,15,19,23,27-heptamethyloctacosa-2,6,10,14,18,22,26-heptaen-1-yl)-3-methylnaphthalen-1-yl benzoate
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: sodium acetate; zinc / 1 h / 140 °C 2: lithium hydroxide; water / tetrahydrofuran / 20 h / 50 °C 3: dmap; dicyclohexyl-carbodiimide / dichloromethane / 20 h / 20 °C View Scheme | |
Multi-step reaction with 3 steps 1.1: sodium acetate; zinc / 1 h / 140 °C 1.2: 1 h / 20 °C 2.1: lithium hydroxide monohydrate; water / tetrahydrofuran / 20 h / 50 °C 3.1: dmap; dicyclohexyl-carbodiimide / dichloromethane / 20 h / 20 °C View Scheme |
menaquinone-7
2-((2E,6E,10E,14E,18E,22E)-3,7,11,15,19,23,27-heptamethyloctacosa-2,6,10,14,18,22,26-heptaen-1-yl)-4-hydroxy-3-methylnaphthalen-1-yl propionate
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: sodium acetate; zinc / 0.5 h / 130 °C 2: lithium hydroxide; water / tetrahydrofuran / 20 h / 50 °C View Scheme |
menaquinone-7
4-((diethoxyphosphoryl)oxy)-2-((2E,6E,10E,14E,18E,22E)-3,7,11,15,19,23,27-heptamethyloctacosa-2,6,10,14,18,22,26-heptaen-1-yl)-3-methylnaphthalen-1-yl propionate
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: sodium acetate; zinc / 0.5 h / 130 °C 2: lithium hydroxide; water / tetrahydrofuran / 20 h / 50 °C 3: triethylamine / dichloromethane / 20 h / 0 - 20 °C View Scheme | |
Multi-step reaction with 3 steps 1: sodium acetate; zinc / 0.5 h / 130 °C 2: lithium hydroxide monohydrate; water / tetrahydrofuran / 20 h / 50 °C 3: triethylamine / dichloromethane / 20 h / 0 - 20 °C View Scheme |
menaquinone-7
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: sodium acetate; zinc / 0.5 h / 130 °C 2: lithium hydroxide; water / tetrahydrofuran / 20 h / 50 °C 3: dmap; dicyclohexyl-carbodiimide / dichloromethane / 20 h / 20 °C View Scheme |
menaquinone-7
4-(((tert-butoxycarbonyl)glycyl)oxy)-2-((2E,6E,10E,14E,18E,22E)-3,7,11,15,19,23,27-heptamethyloctacosa-2,6,10,14,18,22,26-heptaen-1-yl)-3-methylnaphthalen-1-yl propionate
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: sodium acetate; zinc / 0.5 h / 130 °C 2: lithium hydroxide; water / tetrahydrofuran / 20 h / 50 °C 3: dmap; dicyclohexyl-carbodiimide / dichloromethane / 20 h / 20 °C View Scheme | |
Multi-step reaction with 3 steps 1: sodium acetate; zinc / 0.5 h / 130 °C 2: lithium hydroxide monohydrate; water / tetrahydrofuran / 20 h / 50 °C 3: dmap; dicyclohexyl-carbodiimide / dichloromethane / 20 h / 20 °C View Scheme |
menaquinone-7
3-((2E,6E,10E,14E,18E,22E)-3,7,11,15,19,23,27-heptamethyloctacosa-2,6,10,14,18,22,26-heptaen-1-yl)-2-methyl-4-(propionyloxy)naphthalen-1-yl 3-((tert-butoxycarbonyl)amino)propanoate
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: sodium acetate; zinc / 0.5 h / 130 °C 2: lithium hydroxide; water / tetrahydrofuran / 20 h / 50 °C 3: dmap; dicyclohexyl-carbodiimide / dichloromethane / 20 h / 20 °C View Scheme | |
Multi-step reaction with 3 steps 1: sodium acetate; zinc / 0.5 h / 130 °C 2: lithium hydroxide monohydrate; water / tetrahydrofuran / 20 h / 50 °C 3: dmap; dicyclohexyl-carbodiimide / dichloromethane / 20 h / 20 °C View Scheme |
menaquinone-7
4-((3-((2E,6E,10E,14E,18E,22E)-3,7,11,15,19,23,27-heptamethyloctacosa-2,6,10,14,18,22,26-heptaen-1-yl)-2-methyl-4-(propionyloxy)naphthalen-1-yl)oxy)-4-oxobutanoic acid
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: sodium acetate; zinc / 0.5 h / 130 °C 2: lithium hydroxide; water / tetrahydrofuran / 20 h / 50 °C 3: dmap / dichloromethane / 3.5 h / 20 °C View Scheme | |
Multi-step reaction with 3 steps 1: sodium acetate; zinc / 0.5 h / 130 °C 2: lithium hydroxide monohydrate; water / tetrahydrofuran / 20 h / 50 °C 3: dmap / dichloromethane / 3.5 h / 20 °C View Scheme |
menaquinone-7
2-((2E,6E,10E,14E,18E,22E)-3,7,11,15,19,23,27-heptamethyloctacosa-2,6,10,14,18,22,26-heptaen-1-yl)-4-hydroxy-3-methylnaphthalen-1-yl benzoate
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: sodium acetate; zinc / 1 h / 140 °C 2: lithium hydroxide; water / tetrahydrofuran / 20 h / 50 °C View Scheme | |
Multi-step reaction with 2 steps 1.1: sodium acetate; zinc / 1 h / 140 °C 1.2: 1 h / 20 °C 2.1: lithium hydroxide monohydrate; water / tetrahydrofuran / 20 h / 50 °C View Scheme |
Conditions | Yield |
---|---|
With sodium acetate; zinc for 0.5h; Inert atmosphere; Reflux; |
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