8-Tridecen-1-ol,5,11-bis[[(1,1-dimethylethyl)dimethylsilyl]oxy]-3-[(4-methoxyphenyl)methoxy]-2,4,6,10,12-pentamethyl-13-(triphenylmethoxy)-, methanesulfonate,(2S,3S,4R,5R,6S,8Z,10S,11R,12S)-

Base Information

• Chemical Name: 8-Tridecen-1-ol,5,11-bis[[(1,1-dimethylethyl)dimethylsilyl]oxy]-3-[(4-methoxyphenyl)methoxy]-2,4,6,10,12-pentamethyl-13-(triphenylmethoxy)-, methanesulfonate,(2S,3S,4R,5R,6S,8Z,10S,11R,12S)-
• CAS No.: 837383-40-1
• Molecular Formula: C58H88O8SSi2
• Molecular Weight: 1001.57

Synonyms:

Chemical Property of 8-Tridecen-1-ol,5,11-bis[[(1,1-dimethylethyl)dimethylsilyl]oxy]-3-[(4-methoxyphenyl)methoxy]-2,4,6,10,12-pentamethyl-13-(triphenylmethoxy)-, methanesulfonate,(2S,3S,4R,5R,6S,8Z,10S,11R,12S)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 8-Tridecen-1-ol,5,11-bis[[(1,1-dimethylethyl)dimethylsilyl]oxy]-3-[(4-methoxyphenyl)methoxy]-2,4,6,10,12-pentamethyl-13-(triphenylmethoxy)-, methanesulfonate,(2S,3S,4R,5R,6S,8Z,10S,11R,12S)-

There total 6 articles about 8-Tridecen-1-ol,5,11-bis[[(1,1-dimethylethyl)dimethylsilyl]oxy]-3-[(4-methoxyphenyl)methoxy]-2,4,6,10,12-pentamethyl-13-(triphenylmethoxy)-, methanesulfonate,(2S,3S,4R,5R,6S,8Z,10S,11R,12S)- 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: 91.0%

(Z)-(2S,3S,4R,5R,6S,10S,11R,12S)-5,11-Bis-(tert-butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-2,4,6,10,12-pentamethyl-13-trityloxy-tridec-8-en-1-ol (835929-79-8) + methanesulfonyl chloride (124-63-0) → Methanesulfonic acid (Z)-(2S,3S,4R,5R,6S,10S,11R,12S)-5,11-bis-(tert-butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-2,4,6,10,12-pentamethyl-13-trityloxy-tridec-8-enyl ester (837383-40-1)

Guidance literature:

With triethylamine; In dichloromethane; at 20 ℃; for 1h;

DOI:10.1021/ol0476873

Reference yield:

tert-Butyl-{(Z)-(1R,2S)-4-iodo-1-[(S)-2-(4-methoxy-benzyloxy)-1-methyl-ethyl]-2-methyl-but-3-enyloxy}-dimethyl-silane → Methanesulfonic acid (Z)-(2S,3S,4R,5R,6S,10S,11R,12S)-5,11-bis-(tert-butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-2,4,6,10,12-pentamethyl-13-trityloxy-tridec-8-enyl ester (837383-40-1)

Guidance literature:

Multi-step reaction with 5 steps

1.1: ZnCl₂; t-BuLi / diethyl ether; pentane / 1 h / 20 °C

1.2: 60 percent / Pd(PPh₃)4 / diethyl ether; pentane / 20 °C

2.1: 80 percent / H₂O; DDQ / CH₂Cl₂ / 1 h / 0 °C

3.1: 87 percent / pyridine; DMAP / 18 h / Heating

4.1: 96 percent / DIBAL-H / CH₂Cl₂ / 4.5 h / 0 °C

5.1: 91 percent / Et₃N / CH₂Cl₂ / 1 h / 20 °C

With pyridine; dmap; water; tert.-butyl lithium; diisobutylaluminium hydride; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; zinc(II) chloride; In diethyl ether; dichloromethane; pentane;

DOI:10.1021/ol0476873

Reference yield:

(Z)-(2S,3R,4S,8S,9R,10R)-3,9-Bis-(tert-butyl-dimethyl-silanyloxy)-10-[(2S,4S,5S)-2-(4-methoxy-phenyl)-5-methyl-[1,3]dioxan-4-yl]-2,4,8-trimethyl-undec-5-en-1-ol (835929-77-6) → Methanesulfonic acid (Z)-(2S,3S,4R,5R,6S,10S,11R,12S)-5,11-bis-(tert-butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-2,4,6,10,12-pentamethyl-13-trityloxy-tridec-8-enyl ester (837383-40-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 87 percent / pyridine; DMAP / 18 h / Heating

2: 96 percent / DIBAL-H / CH₂Cl₂ / 4.5 h / 0 °C

3: 91 percent / Et₃N / CH₂Cl₂ / 1 h / 20 °C

With pyridine; dmap; diisobutylaluminium hydride; triethylamine; In dichloromethane;

DOI:10.1021/ol0476873

upstream raw materials:

(Z)-(2S,3S,4R,5R,6S,10S,11R,12S)-5,11-Bis-(tert-butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-2,4,6,10,12-pentamethyl-13-trityloxy-tridec-8-en-1-ol

methanesulfonyl chloride

(Z)-(2S,3R,4S,8S,9R,10R)-3,9-Bis-(tert-butyl-dimethyl-silanyloxy)-10-[(2S,4S,5S)-2-(4-methoxy-phenyl)-5-methyl-[1,3]dioxan-4-yl]-2,4,8-trimethyl-undec-5-en-1-ol

(2S,4S,5S)-4-[(Z)-(1R,2R,3S,7S,8R,9S)-2,8-Bis-(tert-butyl-dimethyl-silanyloxy)-10-(4-methoxy-benzyloxy)-1,3,7,9-tetramethyl-dec-5-enyl]-2-(4-methoxy-phenyl)-5-methyl-[1,3]dioxane

Downstream raw materials:

(3R,4S,5S,6S)-4-(tert-Butyl-dimethyl-silanyloxy)-3,5-dimethyl-6-[(3Z,8Z)-(2S,5S,6R,7S,11S,12R,13R,14S)-2,6,12-tris-(tert-butyl-dimethyl-silanyloxy)-14-(4-methoxy-benzyloxy)-5,7,11,13,15-pentamethyl-hexadeca-3,8-dienyl]-tetrahydro-pyran-2-one

(Z)-(2S,3R,4S,8S,9R,10R,11S)-3,9-Bis-(tert-butyl-dimethyl-silanyloxy)-11-(4-methoxy-benzyloxy)-2,4,8,10,12-pentamethyl-tridec-5-en-1-ol

1-[(Z)-(1S,2R,3R,4S,8S,9R,10S)-3,9-Bis-(tert-butyl-dimethyl-silanyloxy)-1-isopropyl-2,4,8,10-tetramethyl-11-trityloxy-undec-6-enyloxymethyl]-4-methoxy-benzene

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