(E)-(S)-6-(tert-Butyl-dimethyl-silanyloxy)-5-(4-methoxy-benzyloxy)-hex-2-en-1-ol

Base Information

• Chemical Name: (E)-(S)-6-(tert-Butyl-dimethyl-silanyloxy)-5-(4-methoxy-benzyloxy)-hex-2-en-1-ol
• CAS No.: 334706-39-7
• Molecular Formula: C₂₀H₃₄O₄Si
• Molecular Weight: 366.573
• Mol file: 334706-39-7.mol

Synonyms:(E)-(S)-6-(tert-Butyl-dimethyl-silanyloxy)-5-(4-methoxy-benzyloxy)-hex-2-en-1-ol

Chemical Property of (E)-(S)-6-(tert-Butyl-dimethyl-silanyloxy)-5-(4-methoxy-benzyloxy)-hex-2-en-1-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E)-(S)-6-(tert-Butyl-dimethyl-silanyloxy)-5-(4-methoxy-benzyloxy)-hex-2-en-1-ol

There total 5 articles about (E)-(S)-6-(tert-Butyl-dimethyl-silanyloxy)-5-(4-methoxy-benzyloxy)-hex-2-en-1-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: 97.0%

(E)-(S)-6-(tert-Butyl-dimethyl-silanyloxy)-5-(4-methoxy-benzyloxy)-hex-2-enoic acid methyl ester (334706-38-6) → (E)-(S)-6-(tert-Butyl-dimethyl-silanyloxy)-5-(4-methoxy-benzyloxy)-hex-2-en-1-ol (334706-39-7)

Guidance literature:

With diisobutylaluminium hydride; In toluene; at -78 ℃; for 2h;

DOI:10.1016/S0040-4039(00)02115-8

Reference yield:

O-(4-methoxybenzyl)-trichloroacetimidate (89238-99-3) → (E)-(S)-6-(tert-Butyl-dimethyl-silanyloxy)-5-(4-methoxy-benzyloxy)-hex-2-en-1-ol (334706-39-7)

Guidance literature:

Multi-step reaction with 5 steps

1: 76 percent / BF₃*OEt₂ / CH₂Cl₂ / 1 h / -78 °C

2: 99 percent / DIBAL / toluene / 0.08 h / -78 °C

3: 90 percent / benzene / 1 h / Heating

4: 99 percent / Et₃N; DMAP / CH₂Cl₂ / 2 h

5: 97 percent / DIBAL / toluene / 2 h / -78 °C

With dmap; boron trifluoride diethyl etherate; diisobutylaluminium hydride; triethylamine; In dichloromethane; toluene; benzene;

DOI:10.1016/S0040-4039(00)02115-8

Reference yield:

(S)-4-(4-Methoxy-benzyloxy)-tetrahydro-furan-2-ol (194540-66-4) → (E)-(S)-6-(tert-Butyl-dimethyl-silanyloxy)-5-(4-methoxy-benzyloxy)-hex-2-en-1-ol (334706-39-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 90 percent / benzene / 1 h / Heating

2: 99 percent / Et₃N; DMAP / CH₂Cl₂ / 2 h

3: 97 percent / DIBAL / toluene / 2 h / -78 °C

With dmap; diisobutylaluminium hydride; triethylamine; In dichloromethane; toluene; benzene;

DOI:10.1016/S0040-4039(00)02115-8

upstream raw materials:

(E)-(S)-6-(tert-Butyl-dimethyl-silanyloxy)-5-(4-methoxy-benzyloxy)-hex-2-enoic acid methyl ester

O-(4-methoxybenzyl)-trichloroacetimidate

(S)-4-(4-Methoxy-benzyloxy)-tetrahydro-furan-2-ol

(S)-4-(4-Methoxy-benzyloxy)-dihydro-furan-2-one

Downstream raw materials:

Benzoic acid (E)-(S)-6-hydroxy-5-(4-methoxy-benzyloxy)-hex-2-enyl ester

Benzoic acid (E)-(S)-5-(4-methoxy-benzyloxy)-6-oxo-hex-2-enyl ester

Benzoic acid (E)-(S)-6-(tert-butyl-dimethyl-silanyloxy)-5-(4-methoxy-benzyloxy)-hex-2-enyl ester