C₆₃H₁₁₁Cl₃O₈Si₄

Base Information

• Chemical Name: C₆₃H₁₁₁Cl₃O₈Si₄
• CAS No.: 1257329-51-3
• Molecular Formula: C₆₃H₁₁₁Cl₃O₈Si₄
• Molecular Weight: 1215.27

Synonyms:

Chemical Property of C₆₃H₁₁₁Cl₃O₈Si₄

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of C₆₃H₁₁₁Cl₃O₈Si₄

There total 24 articles about C₆₃H₁₁₁Cl₃O₈Si₄ 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:

2,4,6-trichlorobenzoyl chloride (4136-95-2) + (2Z,4E,10Z,23Z)-(6R,7S,9R,12S,13R,14S,16S,19R,20R,21S,22S)-7,9,13,19-tetrakis-(tert-butyldimethylsilyloxy)-21-hydroxy-6,12,14,16,20,22-hexamethyl-hexacosa-2,4,10,23,25-pentaenoic acid (1257329-49-9) → C63H111Cl3O8Si4 (1257329-51-3)

Guidance literature:

With triethylamine; In tetrahydrofuran; at 0 ℃; for 1h; Inert atmosphere;

DOI:10.1002/ejoc.201001018

Reference yield:

[2S,4R]-5-(4-methoxy-benzyloxy)-2,4-dimethyl-pentan-1-ol (143236-77-5) → C63H111Cl3O8Si4 (1257329-51-3)

Guidance literature:

Multi-step reaction with 24 steps

1.1: tetra-(n-butyl)ammonium iodide; sodium hydride / tetrahydrofuran / Inert atmosphere

2.1: ammonium cerium (IV) nitrate; water / acetonitrile / 0 °C / Inert atmosphere

3.1: pyridine; Dess-Martin periodane / dichloromethane / Inert atmosphere

4.1: n-butyllithium; diisopropylamine / tetrahydrofuran; diethyl ether / 0.5 h / -78 °C / Inert atmosphere

4.2: -78 - 20 °C / Inert atmosphere

5.1: n-butyllithium / tetrahydrofuran; hexane / 0.58 h / -78 - 0 °C / Inert atmosphere

5.2: 1.08 h / -78 - 0 °C / Inert atmosphere

6.1: (1S,2S)-(+)-N-tosyl-1,2-diphenylethane-1,2-diamine[η6-1-isopropyl-4-methylbenzene]-ruthenium(II) / isopropyl alcohol / 5 h / 20 °C / Inert atmosphere

7.1: diisobutylaluminium hydride / dichloromethane / Inert atmosphere

8.1: Wilkinson's catalyst; hydrogen / benzene / 3000.3 Torr

9.1: 2,6-dimethylpyridine / dichloromethane / Inert atmosphere

10.1: hydrogen / ethanol

11.1: tetrapropylammonium perruthennate; 4-methylmorpholine N-oxide / dichloromethane / Inert atmosphere

12.1: diethylzinc; palladium diacetate; triphenylphosphine / tetrahydrofuran; hexane / -78 - -20 °C / Inert atmosphere

13.1: 2,6-dimethylpyridine / dichloromethane / 2 h / -20 °C / Inert atmosphere

14.1: n-butyllithium / hexane / 1 h / -50 °C / Inert atmosphere

14.2: 1 h / -50 - 20 °C / Inert atmosphere

15.1: 2-nitrobenzenesulfonyl hydrazide; triethylamine / tetrahydrofuran; isopropyl alcohol / 24 h / 20 °C / Inert atmosphere

16.1: pyridine; pyridine hydrogenfluoride / tetrahydrofuran / 0 - 20 °C / Inert atmosphere

17.1: pyridine; Dess-Martin periodane / dichloromethane / 0 - 20 °C / Inert atmosphere

18.1: chromium dichloride / tetrahydrofuran / 0 - 20 °C / Inert atmosphere

19.1: potassium hydroxide / methanol; water / 0 - 20 °C / Inert atmosphere

20.1: tert.-butyl lithium / diethyl ether; pentane / 0.5 h / -78 °C / Inert atmosphere

20.2: 0.25 h / -78 °C / Inert atmosphere

20.3: 1 h / -78 °C / Inert atmosphere

21.1: 2,6-dimethylpyridine / dichloromethane / 1 h / -78 °C / Inert atmosphere

22.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 1 h / 0 °C / pH 7 / aq. phosphate buffer; Inert atmosphere

23.1: water; potassium hydroxide / tetrahydrofuran; ethanol / 5 h / 52 °C / Inert atmosphere

24.1: triethylamine / tetrahydrofuran / 1 h / 0 °C / Inert atmosphere

With pyridine; 2,6-dimethylpyridine; chromium dichloride; Wilkinson's catalyst; (1S,2S)-(+)-N-tosyl-1,2-diphenylethane-1,2-diamine[η6-1-isopropyl-4-methylbenzene]-ruthenium(II); n-butyllithium; ammonium cerium (IV) nitrate; tetrapropylammonium perruthennate; 2-nitrobenzenesulfonyl hydrazide; water; hydrogen; tert.-butyl lithium; diethylzinc; palladium diacetate; tetra-(n-butyl)ammonium iodide; sodium hydride; diisobutylaluminium hydride; Dess-Martin periodane; pyridine hydrogenfluoride; 4-methylmorpholine N-oxide; triethylamine; diisopropylamine; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; potassium hydroxide; In tetrahydrofuran; methanol; diethyl ether; ethanol; hexane; dichloromethane; water; isopropyl alcohol; acetonitrile; pentane; benzene; 3.1: Dess-Martin oxidation / 4.1: Shioiri alkynylation / 4.2: Shioiri alkynylation / 12.1: Marshall-Tamaru addition / 17.1: Dess-Martin oxidation / 18.1: Nozaki-Hiyama-Kishi coupling / 19.1: Peterson olefination;

DOI:10.1002/ejoc.201100244

Reference yield:

(2S,4R)-5-(4-methoxybenzyloxy)-2,4-dimethylpentanoic acid ((1R,2R)-2-hydroxy-1-methyl-2-phenylethyl)-methyl-amide (922523-34-0) → C63H111Cl3O8Si4 (1257329-51-3)

Guidance literature:

Multi-step reaction with 25 steps

1.1: ammonia borane / tetrahydrofuran / Inert atmosphere

2.1: tetra-(n-butyl)ammonium iodide; sodium hydride / tetrahydrofuran / Inert atmosphere

3.1: ammonium cerium (IV) nitrate; water / acetonitrile / 0 °C / Inert atmosphere

4.1: pyridine; Dess-Martin periodane / dichloromethane / Inert atmosphere

5.1: n-butyllithium; diisopropylamine / tetrahydrofuran; diethyl ether / 0.5 h / -78 °C / Inert atmosphere

5.2: -78 - 20 °C / Inert atmosphere

6.1: n-butyllithium / tetrahydrofuran; hexane / 0.58 h / -78 - 0 °C / Inert atmosphere

6.2: 1.08 h / -78 - 0 °C / Inert atmosphere

7.1: (1S,2S)-(+)-N-tosyl-1,2-diphenylethane-1,2-diamine[η6-1-isopropyl-4-methylbenzene]-ruthenium(II) / isopropyl alcohol / 5 h / 20 °C / Inert atmosphere

8.1: diisobutylaluminium hydride / dichloromethane / Inert atmosphere

9.1: Wilkinson's catalyst; hydrogen / benzene / 3000.3 Torr

10.1: 2,6-dimethylpyridine / dichloromethane / Inert atmosphere

11.1: hydrogen / ethanol

12.1: tetrapropylammonium perruthennate; 4-methylmorpholine N-oxide / dichloromethane / Inert atmosphere

13.1: diethylzinc; palladium diacetate; triphenylphosphine / tetrahydrofuran; hexane / -78 - -20 °C / Inert atmosphere

14.1: 2,6-dimethylpyridine / dichloromethane / 2 h / -20 °C / Inert atmosphere

15.1: n-butyllithium / hexane / 1 h / -50 °C / Inert atmosphere

15.2: 1 h / -50 - 20 °C / Inert atmosphere

16.1: 2-nitrobenzenesulfonyl hydrazide; triethylamine / tetrahydrofuran; isopropyl alcohol / 24 h / 20 °C / Inert atmosphere

17.1: pyridine; pyridine hydrogenfluoride / tetrahydrofuran / 0 - 20 °C / Inert atmosphere

18.1: pyridine; Dess-Martin periodane / dichloromethane / 0 - 20 °C / Inert atmosphere

19.1: chromium dichloride / tetrahydrofuran / 0 - 20 °C / Inert atmosphere

20.1: potassium hydroxide / methanol; water / 0 - 20 °C / Inert atmosphere

21.1: tert.-butyl lithium / diethyl ether; pentane / 0.5 h / -78 °C / Inert atmosphere

21.2: 0.25 h / -78 °C / Inert atmosphere

21.3: 1 h / -78 °C / Inert atmosphere

22.1: 2,6-dimethylpyridine / dichloromethane / 1 h / -78 °C / Inert atmosphere

23.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 1 h / 0 °C / pH 7 / aq. phosphate buffer; Inert atmosphere

24.1: water; potassium hydroxide / tetrahydrofuran; ethanol / 5 h / 52 °C / Inert atmosphere

25.1: triethylamine / tetrahydrofuran / 1 h / 0 °C / Inert atmosphere

With pyridine; 2,6-dimethylpyridine; chromium dichloride; Wilkinson's catalyst; (1S,2S)-(+)-N-tosyl-1,2-diphenylethane-1,2-diamine[η6-1-isopropyl-4-methylbenzene]-ruthenium(II); n-butyllithium; ammonium cerium (IV) nitrate; tetrapropylammonium perruthennate; ammonia borane; 2-nitrobenzenesulfonyl hydrazide; water; hydrogen; tert.-butyl lithium; diethylzinc; palladium diacetate; tetra-(n-butyl)ammonium iodide; sodium hydride; diisobutylaluminium hydride; Dess-Martin periodane; pyridine hydrogenfluoride; 4-methylmorpholine N-oxide; triethylamine; diisopropylamine; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; potassium hydroxide; In tetrahydrofuran; methanol; diethyl ether; ethanol; hexane; dichloromethane; water; isopropyl alcohol; acetonitrile; pentane; benzene; 4.1: Dess-Martin oxidation / 5.1: Shioiri alkynylation / 5.2: Shioiri alkynylation / 13.1: Marshall-Tamaru addition / 18.1: Dess-Martin oxidation / 19.1: Nozaki-Hiyama-Kishi coupling / 20.1: Peterson olefination;

DOI:10.1002/ejoc.201100244

upstream raw materials:

2,4,6-trichlorobenzoyl chloride

(2Z,4E,10Z,23Z)-(6R,7S,9R,12S,13R,14S,16S,19R,20R,21S,22S)-7,9,13,19-tetrakis-(tert-butyldimethylsilyloxy)-21-hydroxy-6,12,14,16,20,22-hexamethyl-hexacosa-2,4,10,23,25-pentaenoic acid

(5R,6S,8S,11R)-5-((S,Z)-4-iodobut-3-en-2-yl)-11-((2R,3S,4S,Z)-3-(4-methoxybenzyloxy)-4-methylocta-5,7-dien-2-yl)-2,2,3,3,6,8,13,13,14,14-decamethyl-4,12-dioxa-3,13-disilapentadecane

(2S,4R)-5-(4-methoxybenzyloxy)-2,4-dimethylpentanoic acid ((1R,2R)-2-hydroxy-1-methyl-2-phenylethyl)-methyl-amide

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