((4R,8R)-9-(benzyloxy)-8-methyl-6-methylenenonan-4-yloxy)(tert-butyl)dimethylsilane

Base Information

• Chemical Name: ((4R,8R)-9-(benzyloxy)-8-methyl-6-methylenenonan-4-yloxy)(tert-butyl)dimethylsilane
• CAS No.: 1269803-22-6
• Molecular Formula: C₂₄H₄₂O₂Si
• Molecular Weight: 390.682
• Mol file: 1269803-22-6.mol

Synonyms:((4R,8R)-9-(benzyloxy)-8-methyl-6-methylenenonan-4-yloxy)(tert-butyl)dimethylsilane

Chemical Property of ((4R,8R)-9-(benzyloxy)-8-methyl-6-methylenenonan-4-yloxy)(tert-butyl)dimethylsilane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ((4R,8R)-9-(benzyloxy)-8-methyl-6-methylenenonan-4-yloxy)(tert-butyl)dimethylsilane

There total 16 articles about ((4R,8R)-9-(benzyloxy)-8-methyl-6-methylenenonan-4-yloxy)(tert-butyl)dimethylsilane 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%

(4R,8R)-9-(benzyloxy)-8-methyl-6-methylenenonan-4-ol (1269803-12-4) + tert-butyldimethylsilyl chloride (18162-48-6) → ((4R,8R)-9-(benzyloxy)-8-methyl-6-methylenenonan-4-yloxy)(tert-butyl)dimethylsilane (1269803-22-6)

Guidance literature:

With 1H-imidazole; In dichloromethane; at 0 - 20 ℃; for 3.16667h; Inert atmosphere;

DOI:10.1002/ejoc.201001205

Reference yield: 77.0%

(2R)-4-((2R)-2-[1-(tert-butyl)-1,1-dimethylsilyl]oxypentyl)-2-methyl-4-penten-1-ol (900159-60-6) + benzyl bromide (100-39-0) → ((4R,8R)-9-(benzyloxy)-8-methyl-6-methylenenonan-4-yloxy)(tert-butyl)dimethylsilane (1269803-22-6)

Guidance literature:

(2R)-4-((2R)-2-[1-(tert-butyl)-1,1-dimethylsilyl]oxypentyl)-2-methyl-4-penten-1-ol; With sodium hydride; In tetrahydrofuran; paraffin oil; at 0 ℃; for 0.5h;

benzyl bromide; In tetrahydrofuran; paraffin oil; at 20 ℃; for 2h;

DOI:10.1016/j.tet.2012.11.075

Reference yield:

1-{[(R)-4-(bromomethyl)-2-methylpent-4-enyloxy]methyl}benzene (1269803-29-3) → ((4R,8R)-9-(benzyloxy)-8-methyl-6-methylenenonan-4-yloxy)(tert-butyl)dimethylsilane (1269803-22-6)

Guidance literature:

Multi-step reaction with 4 steps

1.1: zinc / tetrahydrofuran / 1 h / Inert atmosphere

1.2: 3 h / 20 °C / Inert atmosphere

2.1: lipase PS-C Amano II / di-isopropyl ether / 96 h / 20 °C / kinetic resolution; Enzymatic reaction

3.1: sodium / methanol / 1.17 h / 0 - 20 °C / Inert atmosphere

4.1: 1H-imidazole / dichloromethane / 3.17 h / 0 - 20 °C / Inert atmosphere

With 1H-imidazole; sodium; zinc; In tetrahydrofuran; methanol; dichloromethane; di-isopropyl ether; 1.2: Barbier reaction;

DOI:10.1002/ejoc.201001205

upstream raw materials:

(R)-5-(benzyloxy)-4-methyl-2-methylenepentan-1-ol

1-{[(R)-4-(bromomethyl)-2-methylpent-4-enyloxy]methyl}benzene

(R)-8-[(benzyloxy)methyl]-6-methylenenonan-4-ol

(4R,8R)-9-(benzyloxy)-8-methyl-6-methylenenonan-4-yl acetate

Downstream raw materials:

(S)-((4R,8R)-9-(benzyloxy)-8-methyl-6-methylenenonan-4-yl)-6-((2S,3S,5R)-5-(2-(4-methoxybenzyloxy)ethyl)-3-methyltetrahydrofuran-2-yl)-2-methylhexanoate

(4R,8R)-9-(benzyloxy)-8-methyl-6-methylenenonan-4-ol