[(Z)-(R)-2,6-Bis-(tert-butyl-dimethyl-silanyloxy)-4-methyl-hex-4-enyloxymethyl]-benzene

Base Information

• Chemical Name: [(Z)-(R)-2,6-Bis-(tert-butyl-dimethyl-silanyloxy)-4-methyl-hex-4-enyloxymethyl]-benzene
• CAS No.: 389123-39-1
• Molecular Formula: C₂₆H₄₈O₃Si₂
• Molecular Weight: 464.836
• Mol file: 389123-39-1.mol

Synonyms:[(Z)-(R)-2,6-Bis-(tert-butyl-dimethyl-silanyloxy)-4-methyl-hex-4-enyloxymethyl]-benzene

Chemical Property of [(Z)-(R)-2,6-Bis-(tert-butyl-dimethyl-silanyloxy)-4-methyl-hex-4-enyloxymethyl]-benzene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [(Z)-(R)-2,6-Bis-(tert-butyl-dimethyl-silanyloxy)-4-methyl-hex-4-enyloxymethyl]-benzene

There total 3 articles about [(Z)-(R)-2,6-Bis-(tert-butyl-dimethyl-silanyloxy)-4-methyl-hex-4-enyloxymethyl]-benzene 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%

t-butyldimethylsiyl triflate (69739-34-0) + (Z)-(R)-6-Benzyloxy-3-methyl-hex-2-ene-1,5-diol (389123-24-4) → [(Z)-(R)-2,6-Bis-(tert-butyl-dimethyl-silanyloxy)-4-methyl-hex-4-enyloxymethyl]-benzene (389123-39-1)

Guidance literature:

With 2,6-dimethylpyridine; In dichloromethane; at -78 ℃; for 1.5h;

DOI:10.1021/ja020635t

Reference yield:

(R)-ethyl 6-(benzyloxy)-5-hydroxyhex-2-ynoate (197520-87-9) → [(Z)-(R)-2,6-Bis-(tert-butyl-dimethyl-silanyloxy)-4-methyl-hex-4-enyloxymethyl]-benzene (389123-39-1)

Guidance literature:

Multi-step reaction with 3 steps

1.1: CuI / tetrahydrofuran; diethyl ether / 0.17 h / 0 °C

1.2: 78 percent / tetrahydrofuran; diethyl ether / 1.17 h / -78 °C

2.1: 96 percent / DIBAL-H / tetrahydrofuran; toluene / -78 - 0 °C

3.1: 88 percent / 2,6-lutidine / CH₂Cl₂ / 1.5 h / -78 °C

With 2,6-dimethylpyridine; copper(l) iodide; diisobutylaluminium hydride; In tetrahydrofuran; diethyl ether; dichloromethane; toluene; 1.1: Michael addition;

DOI:10.1021/ja020635t

Reference yield:

(Z)-(R)-6-Benzyloxy-5-hydroxy-3-methyl-hex-2-enoic acid ethyl ester (389123-38-0) → [(Z)-(R)-2,6-Bis-(tert-butyl-dimethyl-silanyloxy)-4-methyl-hex-4-enyloxymethyl]-benzene (389123-39-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 96 percent / DIBAL-H / tetrahydrofuran; toluene / -78 - 0 °C

2: 88 percent / 2,6-lutidine / CH₂Cl₂ / 1.5 h / -78 °C

With 2,6-dimethylpyridine; diisobutylaluminium hydride; In tetrahydrofuran; dichloromethane; toluene;

DOI:10.1021/ja020635t

upstream raw materials:

t-butyldimethylsiyl triflate

(Z)-(R)-6-Benzyloxy-3-methyl-hex-2-ene-1,5-diol

(R)-ethyl 6-(benzyloxy)-5-hydroxyhex-2-ynoate

(Z)-(R)-6-Benzyloxy-5-hydroxy-3-methyl-hex-2-enoic acid ethyl ester

Downstream raw materials:

(diethoxy-phosphoryl)-acetic acid 4-{6-[4,8-bis-(tert-butyl-dimethyl-silanyloxy)-6-methyl-octa-2,6-dienyl]-4-methylene-tetrahydro-pyran-2-yl}-1-[2-(3,4-dimethoxy-benzyloxy)-1-(4-methoxy-benzyloxy)-ethyl]-3-methyl-but-3-enyl ester

(diethoxy-phosphoryl)-acetic acid 4-{6-[4,8-bis-(tert-butyl-dimethyl-silanyloxy)-6-methyl-octa-2,6-dienyl]-4-methylene-tetrahydro-pyran-2-yl}-1-[2-(3,4-dimethoxy-benzyloxy)-1-(4-methoxy-benzyloxy)-ethyl]-3-methyl-but-3-enyl ester

(diethoxy-phosphoryl)-acetic acid 4-{6-[4-(tert-butyl-dimethyl-silanyloxy)-8-hydroxy-6-methyl-octa-2,6-dienyl]-4-methylene-tetrahydro-pyran-2-yl}-1-[2-(3,4-dimethoxy-benzyloxy)-1-(4-methoxy-benzyloxy)-ethyl]-3-methyl-but-3-enyl ester

(diethoxy-phosphoryl)-acetic acid 4-{6-[4-(tert-butyl-dimethyl-silanyloxy)-8-hydroxy-6-methyl-octa-2,6-dienyl]-4-methylene-tetrahydro-pyran-2-yl}-1-[2-(3,4-dimethoxy-benzyloxy)-1-(4-methoxy-benzyloxy)-ethyl]-3-methyl-but-3-enyl ester