methyl (2Z,4E,6R,7S,9S,10Z,12R,13S,14S,16S,19R,20R,21S,22S,23Z)-7,9,13,19-tetrakis(tert-butyldimethylsilyloxy)-21-(4-methoxybenzyloxy)-6,12,14,16,20,22-hexamethylhexacosa-2,4,10,23,25-pentaenoate

Base Information

• Chemical Name: methyl (2Z,4E,6R,7S,9S,10Z,12R,13S,14S,16S,19R,20R,21S,22S,23Z)-7,9,13,19-tetrakis(tert-butyldimethylsilyloxy)-21-(4-methoxybenzyloxy)-6,12,14,16,20,22-hexamethylhexacosa-2,4,10,23,25-pentaenoate
• CAS No.: 1309460-62-5
• Molecular Formula: C₆₅H₁₂₀O₈Si₄
• Molecular Weight: 1142.01

Synonyms:methyl (2Z,4E,6R,7S,9S,10Z,12R,13S,14S,16S,19R,20R,21S,22S,23Z)-7,9,13,19-tetrakis(tert-butyldimethylsilyloxy)-21-(4-methoxybenzyloxy)-6,12,14,16,20,22-hexamethylhexacosa-2,4,10,23,25-pentaenoate

Chemical Property of methyl (2Z,4E,6R,7S,9S,10Z,12R,13S,14S,16S,19R,20R,21S,22S,23Z)-7,9,13,19-tetrakis(tert-butyldimethylsilyloxy)-21-(4-methoxybenzyloxy)-6,12,14,16,20,22-hexamethylhexacosa-2,4,10,23,25-pentaenoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl (2Z,4E,6R,7S,9S,10Z,12R,13S,14S,16S,19R,20R,21S,22S,23Z)-7,9,13,19-tetrakis(tert-butyldimethylsilyloxy)-21-(4-methoxybenzyloxy)-6,12,14,16,20,22-hexamethylhexacosa-2,4,10,23,25-pentaenoate

There total 22 articles about methyl (2Z,4E,6R,7S,9S,10Z,12R,13S,14S,16S,19R,20R,21S,22S,23Z)-7,9,13,19-tetrakis(tert-butyldimethylsilyloxy)-21-(4-methoxybenzyloxy)-6,12,14,16,20,22-hexamethylhexacosa-2,4,10,23,25-pentaenoate 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: 100.0%

methyl (2Z,4E,6R,7S,9S,10Z,12R,13S,14S,16S,19R,20R,21S,22S,23Z)-7,13,19-tris(tert-butyldimethylsilyloxy)-9-hydroxy-21-(4-methoxybenzyloxy)-6,12,14,16,20,22-hexamethylhexacosa-2,4,10,23,25-pentaenoate (1309460-59-0) + t-butyldimethylsiyl triflate (69739-34-0) → methyl (2Z,4E,6R,7S,9S,10Z,12R,13S,14S,16S,19R,20R,21S,22S,23Z)-7,9,13,19-tetrakis(tert-butyldimethylsilyloxy)-21-(4-methoxybenzyloxy)-6,12,14,16,20,22-hexamethylhexacosa-2,4,10,23,25-pentaenoate (1309460-62-5)

Guidance literature:

With 2,6-dimethylpyridine; In dichloromethane; at -78 ℃; for 2h; Inert atmosphere;

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) → methyl (2Z,4E,6R,7S,9S,10Z,12R,13S,14S,16S,19R,20R,21S,22S,23Z)-7,9,13,19-tetrakis(tert-butyldimethylsilyloxy)-21-(4-methoxybenzyloxy)-6,12,14,16,20,22-hexamethylhexacosa-2,4,10,23,25-pentaenoate (1309460-62-5)

Guidance literature:

Multi-step reaction with 22 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 / 1.5 h / 0 °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 / 2 h / -78 °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; 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

Reference yield:

1-((2R,4S)-5-benzyloxy-2,4-dimethylpentyloxymethyl)-4-methoxybenzene → methyl (2Z,4E,6R,7S,9S,10Z,12R,13S,14S,16S,19R,20R,21S,22S,23Z)-7,9,13,19-tetrakis(tert-butyldimethylsilyloxy)-21-(4-methoxybenzyloxy)-6,12,14,16,20,22-hexamethylhexacosa-2,4,10,23,25-pentaenoate (1309460-62-5)

Guidance literature:

Multi-step reaction with 20 steps

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

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

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

3.2: -78 - 20 °C / Inert atmosphere

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

4.2: 1.08 h / -78 - 0 °C / Inert atmosphere

5.1: (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

6.1: diisobutylaluminium hydride / dichloromethane / Inert atmosphere

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

8.1: 2,6-dimethylpyridine / dichloromethane / Inert atmosphere

9.1: hydrogen / ethanol

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

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

12.1: 2,6-dimethylpyridine / dichloromethane / 1.5 h / 0 °C / Inert atmosphere

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

13.2: 1 h / -50 - 20 °C / Inert atmosphere

14.1: 2-nitrobenzenesulfonyl hydrazide; triethylamine / tetrahydrofuran; isopropyl alcohol / 24 h / 20 °C / Inert atmosphere

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

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

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

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

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

19.2: 0.25 h / -78 °C / Inert atmosphere

19.3: 1 h / -78 °C / Inert atmosphere

20.1: 2,6-dimethylpyridine / dichloromethane / 2 h / -78 °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; diisobutylaluminium hydride; Dess-Martin periodane; pyridine hydrogenfluoride; 4-methylmorpholine N-oxide; triethylamine; diisopropylamine; triphenylphosphine; potassium hydroxide; In tetrahydrofuran; methanol; diethyl ether; ethanol; hexane; dichloromethane; water; isopropyl alcohol; acetonitrile; pentane; benzene; 2.1: Dess-Martin oxidation / 3.1: Shioiri alkynylation / 3.2: Shioiri alkynylation / 11.1: Marshall-Tamaru addition / 16.1: Dess-Martin oxidation / 17.1: Nozaki-Hiyama-Kishi coupling / 18.1: Peterson olefination;

DOI:10.1002/ejoc.201100244

upstream raw materials:

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

({[(2S,4R)-2,4-dimethylhex-5-yn-1-yl]oxy}methyl)benzene

(2S,4S,7R,8R,9S,10S)-7,11-bis(tert-butyldimethylsilanyloxy)-9-(4-methoxybenzyloxy)-2,4,8,10-tetramethylundecanal

(2R,6R,8S)-9-(benzyloxy)-2-[(4S,5S)-2-(4-methoxyphenyl)-5-methyl-1,3-dioxan-4-yl]-6,8-dimethylnon-4-yn-3-one

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