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

Base Information

• Chemical Name: 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
• CAS No.: 1309460-59-0
• Molecular Formula: C₅₉H₁₀₆O₈Si₃
• Molecular Weight: 1027.74

Synonyms: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

Chemical Property of 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

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)-7,13,19-tris(tert-butyldimethylsilyloxy)-9-hydroxy-21-(4-methoxybenzyloxy)-6,12,14,16,20,22-hexamethylhexacosa-2,4,10,23,25-pentaenoate

There total 11 articles about 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 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: 40.0%

methyl (2Z,4E)-(6R,7S)-7-(tert-butyldimethylsilyloxy)-6-methyl-9-oxo-nona-2,4-dienoate (945402-29-9) + (5S,6S,8S,11R)-5-[(R,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 (1309460-58-9) → C42H76O4Si2 + 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)

Guidance literature:

(5S,6S,8S,11R)-5-[(R,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; With tert.-butyl lithium; In diethyl ether; pentane; at -78 ℃; for 0.5h; Inert atmosphere;

With dimethyl zinc(II); In diethyl ether; toluene; pentane; at -78 ℃; for 0.25h; Inert atmosphere;

methyl (2Z,4E)-(6R,7S)-7-(tert-butyldimethylsilyloxy)-6-methyl-9-oxo-nona-2,4-dienoate; In diethyl ether; toluene; pentane; at -78 ℃; for 1h; optical yield given as %de; Inert atmosphere;

DOI:10.1002/ejoc.201100244

Reference yield:

(2R,4S)-5-benzyloxy-2,4-dimethylpentanal → C42H76O4Si2 + 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)

Guidance literature:

Multi-step reaction with 17 steps

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

1.2: -78 - 20 °C / Inert atmosphere

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

2.2: 1.08 h / -78 - 0 °C / Inert atmosphere

3.1: (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

4.1: diisobutylaluminium hydride / dichloromethane / Inert atmosphere

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

6.1: 2,6-dimethylpyridine / dichloromethane / Inert atmosphere

7.1: hydrogen / ethanol

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

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

10.1: 2,6-dimethylpyridine / dichloromethane / 1.5 h / 0 °C / Inert atmosphere

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

11.2: 1 h / -50 - 20 °C / Inert atmosphere

12.1: 2-nitrobenzenesulfonyl hydrazide; triethylamine / tetrahydrofuran; isopropyl alcohol / 24 h / 20 °C / Inert atmosphere

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

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

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

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

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

17.2: 0.25 h / -78 °C / Inert atmosphere

17.3: 1 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; tetrapropylammonium perruthennate; 2-nitrobenzenesulfonyl hydrazide; 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; pentane; benzene; 1.1: Shioiri alkynylation / 1.2: Shioiri alkynylation / 9.1: Marshall-Tamaru addition / 14.1: Dess-Martin oxidation / 15.1: Nozaki-Hiyama-Kishi coupling / 16.1: Peterson olefination;

DOI:10.1002/ejoc.201100244

Reference yield:

[2S,4R]-5-(4-methoxy-benzyloxy)-2,4-dimethyl-pentan-1-ol (143236-77-5) → C42H76O4Si2 + 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)

Guidance literature:

Multi-step reaction with 20 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 / 1.5 h / 0 °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

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; 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

upstream raw materials:

methyl (2Z,4E)-(6R,7S)-7-(tert-butyldimethylsilyloxy)-6-methyl-9-oxo-nona-2,4-dienoate

(5S,6S,8S,11R)-5-[(R,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)-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

Downstream raw materials:

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

(R,2Z,4E)-methyl 6-((4S,6S)-6-{(1Z,3R,4S,5S,7S,10R,11S,12S,13S,14Z)-4,10-dihydroxy-12-[(4-methoxybenzyl)oxy]-3,5,7,11,13-pentamethylheptadeca-1,14,16-trien-1-yl}-2,2-dimethyl-1,3-dioxan-4-yl)hepta-2,4-dienoate

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

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