C₄₀H₆₂O₉

Base Information

• Chemical Name: C₄₀H₆₂O₉
• CAS No.: 1360572-11-7
• Molecular Formula: C₄₀H₆₂O₉
• Molecular Weight: 686.927

Synonyms:

Chemical Property of C₄₀H₆₂O₉

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of C₄₀H₆₂O₉

There total 17 articles about C₄₀H₆₂O₉ which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

(2R,3R,4R)-2,4-dimethylhept-5-yn-1,3-diol (1360572-18-4) → C40H62O9 (1360572-11-7)

Guidance literature:

Multi-step reaction with 9 steps

1.1: pyridinium p-toluenesulfonate / dichloromethane / 1 h / Molecular sieve; Inert atmosphere

2.1: diisobutylaluminium hydride / hexane; dichloromethane / 3.83 h / -78 - 20 °C / Inert atmosphere

3.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 1.58 h / -78 - -40 °C / Inert atmosphere

3.2: -40 - 20 °C / Inert atmosphere

4.1: boron trifluoride diethyl etherate / toluene / 0.5 h / -78 °C / Inert atmosphere

5.1: N,N,N',N'-tetramethyl-1,8-diaminonaphthalene / dichloromethane / 20 °C / Inert atmosphere

6.1: Schwartz's reagent / benzene / Inert atmosphere; Heating

6.2: -25 °C / Inert atmosphere

7.1: chromium dichloride; 1,3-bis[(diphenylphosphino)propane]dichloronickel(II); (R)-N-(2-(4-isopropyl-4,5-dihydrooxazol-2-yl)-6-methylphenyl)methanesulfonamide; N,N,N',N'-tetramethyl-1,8-diaminonaphthalene / acetonitrile / 20 °C / Inert atmosphere

8.1: water; lithium hydroxide / tetrahydrofuran / 20 °C / Inert atmosphere

9.1: dmap; 2-methyl-6-nitrobenzoic anhydride / toluene / Inert atmosphere; Molecular sieve; Heating

With chromium dichloride; dmap; Schwartz's reagent; oxalyl dichloride; (R)-N-(2-(4-isopropyl-4,5-dihydrooxazol-2-yl)-6-methylphenyl)methanesulfonamide; 1,3-bis[(diphenylphosphino)propane]dichloronickel(II); boron trifluoride diethyl etherate; 2-methyl-6-nitrobenzoic anhydride; water; pyridinium p-toluenesulfonate; N,N,N',N'-tetramethyl-1,8-diaminonaphthalene; diisobutylaluminium hydride; dimethyl sulfoxide; lithium hydroxide; In tetrahydrofuran; hexane; dichloromethane; toluene; acetonitrile; benzene; 3.1: Swarts reaction / 7.1: Nozaki-Hiyama-Kishi reaction;

DOI:10.1002/anie.201106762

Reference yield:

pent-3-yn-2-one (7299-55-0) → C40H62O9 (1360572-11-7)

Guidance literature:

Multi-step reaction with 13 steps

1.1: (1S,2S)-(+)-N-tosyl-1,2-diphenylethane-1,2-diamine[η6-1-isopropyl-4-methylbenzene]-ruthenium(II); isopropyl alcohol / dichloromethane / 16 h / 20 °C / Inert atmosphere

2.1: triethylamine / dichloromethane / 2 h / -78 °C / Inert atmosphere

3.1: indium iodide; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ / tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide / 17 h / 20 °C / Inert atmosphere

4.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 13.58 h / 0 - 20 °C / Inert atmosphere

5.1: pyridinium p-toluenesulfonate / dichloromethane / 1 h / Molecular sieve; Inert atmosphere

6.1: diisobutylaluminium hydride / hexane; dichloromethane / 3.83 h / -78 - 20 °C / Inert atmosphere

7.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 1.58 h / -78 - -40 °C / Inert atmosphere

7.2: -40 - 20 °C / Inert atmosphere

8.1: boron trifluoride diethyl etherate / toluene / 0.5 h / -78 °C / Inert atmosphere

9.1: N,N,N',N'-tetramethyl-1,8-diaminonaphthalene / dichloromethane / 20 °C / Inert atmosphere

10.1: Schwartz's reagent / benzene / Inert atmosphere; Heating

10.2: -25 °C / Inert atmosphere

11.1: chromium dichloride; 1,3-bis[(diphenylphosphino)propane]dichloronickel(II); (R)-N-(2-(4-isopropyl-4,5-dihydrooxazol-2-yl)-6-methylphenyl)methanesulfonamide; N,N,N',N'-tetramethyl-1,8-diaminonaphthalene / acetonitrile / 20 °C / Inert atmosphere

12.1: water; lithium hydroxide / tetrahydrofuran / 20 °C / Inert atmosphere

13.1: dmap; 2-methyl-6-nitrobenzoic anhydride / toluene / Inert atmosphere; Molecular sieve; Heating

With chromium dichloride; dmap; Schwartz's reagent; (1S,2S)-(+)-N-tosyl-1,2-diphenylethane-1,2-diamine[η6-1-isopropyl-4-methylbenzene]-ruthenium(II); dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; oxalyl dichloride; (R)-N-(2-(4-isopropyl-4,5-dihydrooxazol-2-yl)-6-methylphenyl)methanesulfonamide; indium iodide; 1,3-bis[(diphenylphosphino)propane]dichloronickel(II); boron trifluoride diethyl etherate; 2-methyl-6-nitrobenzoic anhydride; tetrabutyl ammonium fluoride; water; pyridinium p-toluenesulfonate; N,N,N',N'-tetramethyl-1,8-diaminonaphthalene; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; isopropyl alcohol; lithium hydroxide; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; hexane; dichloromethane; toluene; acetonitrile; benzene; 3.1: Marshall reaction / 7.1: Swarts reaction / 11.1: Nozaki-Hiyama-Kishi reaction;

DOI:10.1002/anie.201106762

Reference yield:

(2R,3R,4R)-1-((tert-butyldiphenylsilyl)oxy)-2,4-dimethylhept-5-yn-3-ol (1360572-05-9) → C40H62O9 (1360572-11-7)

Guidance literature:

Multi-step reaction with 10 steps

1.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 13.58 h / 0 - 20 °C / Inert atmosphere

2.1: pyridinium p-toluenesulfonate / dichloromethane / 1 h / Molecular sieve; Inert atmosphere

3.1: diisobutylaluminium hydride / hexane; dichloromethane / 3.83 h / -78 - 20 °C / Inert atmosphere

4.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 1.58 h / -78 - -40 °C / Inert atmosphere

4.2: -40 - 20 °C / Inert atmosphere

5.1: boron trifluoride diethyl etherate / toluene / 0.5 h / -78 °C / Inert atmosphere

6.1: N,N,N',N'-tetramethyl-1,8-diaminonaphthalene / dichloromethane / 20 °C / Inert atmosphere

7.1: Schwartz's reagent / benzene / Inert atmosphere; Heating

7.2: -25 °C / Inert atmosphere

8.1: chromium dichloride; 1,3-bis[(diphenylphosphino)propane]dichloronickel(II); (R)-N-(2-(4-isopropyl-4,5-dihydrooxazol-2-yl)-6-methylphenyl)methanesulfonamide; N,N,N',N'-tetramethyl-1,8-diaminonaphthalene / acetonitrile / 20 °C / Inert atmosphere

9.1: water; lithium hydroxide / tetrahydrofuran / 20 °C / Inert atmosphere

10.1: dmap; 2-methyl-6-nitrobenzoic anhydride / toluene / Inert atmosphere; Molecular sieve; Heating

With chromium dichloride; dmap; Schwartz's reagent; oxalyl dichloride; (R)-N-(2-(4-isopropyl-4,5-dihydrooxazol-2-yl)-6-methylphenyl)methanesulfonamide; 1,3-bis[(diphenylphosphino)propane]dichloronickel(II); boron trifluoride diethyl etherate; 2-methyl-6-nitrobenzoic anhydride; tetrabutyl ammonium fluoride; water; pyridinium p-toluenesulfonate; N,N,N',N'-tetramethyl-1,8-diaminonaphthalene; diisobutylaluminium hydride; dimethyl sulfoxide; lithium hydroxide; In tetrahydrofuran; hexane; dichloromethane; toluene; acetonitrile; benzene; 4.1: Swarts reaction / 8.1: Nozaki-Hiyama-Kishi reaction;

DOI:10.1002/anie.201106762

upstream raw materials:

C₄₁H₆₄O₁₀

C₄₀H₆₄O₁₀

(2R,3R,6R,10S,E)-methyl-2,3,11-trihydroxy-6,10-dimethylundec-4-enoate

(4R,5R)-methyl 5-[(3R,7S,E)-8-hydroxy-3,7-dimethyloct-1-en-1-yl]-2,2-dimethyl-1,3-dioxolane-4-carboxylate

Downstream raw materials:

C₃₆H₅₄O₉

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