(5R,7S,9R)-2,2,3,3,11,11,12,12-octamethyl-5-((E)-3-methyl-5-phenylpent-3-en-1-yl)-9-((E)-2-methylhexa-2,5-dien-1-yl)-4,10-dioxa-3,11-disilatridecan-7-ol

Base Information

• Chemical Name: (5R,7S,9R)-2,2,3,3,11,11,12,12-octamethyl-5-((E)-3-methyl-5-phenylpent-3-en-1-yl)-9-((E)-2-methylhexa-2,5-dien-1-yl)-4,10-dioxa-3,11-disilatridecan-7-ol
• CAS No.: 1376331-08-6
• Molecular Formula: C₃₆H₆₄O₃Si₂
• Molecular Weight: 601.073

Synonyms:(5R,7S,9R)-2,2,3,3,11,11,12,12-octamethyl-5-((E)-3-methyl-5-phenylpent-3-en-1-yl)-9-((E)-2-methylhexa-2,5-dien-1-yl)-4,10-dioxa-3,11-disilatridecan-7-ol

Chemical Property of (5R,7S,9R)-2,2,3,3,11,11,12,12-octamethyl-5-((E)-3-methyl-5-phenylpent-3-en-1-yl)-9-((E)-2-methylhexa-2,5-dien-1-yl)-4,10-dioxa-3,11-disilatridecan-7-ol

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Technology Process of (5R,7S,9R)-2,2,3,3,11,11,12,12-octamethyl-5-((E)-3-methyl-5-phenylpent-3-en-1-yl)-9-((E)-2-methylhexa-2,5-dien-1-yl)-4,10-dioxa-3,11-disilatridecan-7-ol

There total 17 articles about (5R,7S,9R)-2,2,3,3,11,11,12,12-octamethyl-5-((E)-3-methyl-5-phenylpent-3-en-1-yl)-9-((E)-2-methylhexa-2,5-dien-1-yl)-4,10-dioxa-3,11-disilatridecan-7-ol 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: 88.0%

(5R,7S,9R)-2,2,3,3,11,11,12,12-octamethyl-5-((E)-3-methyl-5-phenylpent-3-en-1-yl)-9-((E)-2-methylhexa-2,5-dien-1-yl)-4,10-dioxa-3,11-disilatridecan-7-yl propionate (1376331-29-1) → (5R,7S,9R)-2,2,3,3,11,11,12,12-octamethyl-5-((E)-3-methyl-5-phenylpent-3-en-1-yl)-9-((E)-2-methylhexa-2,5-dien-1-yl)-4,10-dioxa-3,11-disilatridecan-7-ol (1376331-08-6)

Guidance literature:

With diisobutylaluminium hydride; In dichloromethane; toluene; at -78 ℃; for 1h; Inert atmosphere;

DOI:10.1002/anie.201200871

Reference yield:

(2E,6R,8S,10R,12E)-10-((tert-butyldimethylsilyl)oxy)-6-hydroxy-3,12-dimethyl-1-phenylhexadeca-2,12,15-trien-8-yl propionate (1376331-05-3) → (5R,7S,9R)-2,2,3,3,11,11,12,12-octamethyl-5-((E)-3-methyl-5-phenylpent-3-en-1-yl)-9-((E)-2-methylhexa-2,5-dien-1-yl)-4,10-dioxa-3,11-disilatridecan-7-ol (1376331-08-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 1H-imidazole / N,N-dimethyl-formamide / 20 h / 20 °C / Inert atmosphere

2: diisobutylaluminium hydride / dichloromethane; toluene / 1 h / -78 °C / Inert atmosphere

With 1H-imidazole; diisobutylaluminium hydride; In dichloromethane; N,N-dimethyl-formamide; toluene;

DOI:10.1002/anie.201200871

Reference yield:

(E)-5-methyl-7-phenylhept-5-en-2-one (1375950-76-7) → (5R,7S,9R)-2,2,3,3,11,11,12,12-octamethyl-5-((E)-3-methyl-5-phenylpent-3-en-1-yl)-9-((E)-2-methylhexa-2,5-dien-1-yl)-4,10-dioxa-3,11-disilatridecan-7-ol (1376331-08-6)

Guidance literature:

Multi-step reaction with 4 steps

1.1: triethylamine; B-chlorodiisopinocampheylborane / dichloromethane / 3 h / -78 °C / Inert atmosphere

1.2: 16 h / -78 - -20 °C / Inert atmosphere

1.3: 1.5 h / 0 °C / pH 7 / aq. phosphate buffer

2.1: samarium diiodide / tetrahydrofuran / 1 h / -20 °C / Inert atmosphere

3.1: 1H-imidazole / N,N-dimethyl-formamide / 20 h / 20 °C / Inert atmosphere

4.1: diisobutylaluminium hydride / dichloromethane; toluene / 1 h / -78 °C / Inert atmosphere

With 1H-imidazole; samarium diiodide; diisobutylaluminium hydride; triethylamine; B-chlorodiisopinocampheylborane; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; toluene; 1.1: Paterson aldol reaction / 1.2: Paterson aldol reaction / 2.1: Evans-Tishchenko reduction;

DOI:10.1002/anie.201200871

upstream raw materials:

(E)-5-methyl-7-phenylhept-5-en-2-one

(R,E)-5-((tert-butyldimethylsilyl)oxy)-7-((4-methoxybenzyl)oxy)-3-methylhept-2-en-1-ol

(R,E)-((7-bromo-1-((4-methoxybenzyl)oxy)-5-methylhept-5-en-3-yl)oxy)(tertbutyl)dimethylsilane

(R,E)-tert-butyl((1-((4-methoxybenzyl)oxy)-5-methylnona-5,8-dien-3-yl)oxy)dimethylsilane

Downstream raw materials:

(Z)-(5R,7S,9R)-2,2,3,3,11,11,12,12-octamethyl-5-((E)-3-methyl-5-phenylpent-3-en-1-yl)-9-((E)-2-methylhexa-2,5-dien-1-yl)-4,10-dioxa-3,11-disilatridecan-7-yl 5-((tert-butyldimethylsilyl)oxy)-3-iodopent-2-enoate

(3E,6E,9E,12R,14S)-12-((tert-butyldimethylsilyl)oxy)-14-((R,E)-2-((tert-butyldimethylsilyl)oxy)-5-methyl-7-phenylhept-5-en-1-yl)-4-(2-hydroxyethyl)-10-methyloxacyclotetradeca-3,6,9-trien-2-one

(E)-(5R,7S,9R)-2,2,3,3,11,11,12,12-octamethyl-5-((E)-3-methyl-5-phenylpent-3-en-1-yl)-9-((E)-2-methylhexa-2,5-dien-1-yl)-4,10-dioxa-3,11-disilatridecan-7-yl 3-(2-((tert-butyldimethylsilyl)oxy)ethyl)hexa-2,5-dienoate

(3E,6E,9E,12R,14S)-12-((tert-butyldimethylsilyl)oxy)-14-((R,E)-2-((tert-butyldimethylsilyl)oxy)-5-methyl-7-phenylhept-5-en-1-yl)-4-(2-((tert-butyldimethylsilyl)oxy)ethyl)-10-methyloxacyclotetradeca-3,6,9-trien-2-one

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