(E,2R)-1-(Benzyloxy)-2-methyl-5-(tert-butyldimethylsiloxy)-3-pentene

Base Information

• Chemical Name: (E,2R)-1-(Benzyloxy)-2-methyl-5-(tert-butyldimethylsiloxy)-3-pentene
• CAS No.: 121012-22-4
• Molecular Formula: C₁₉H₃₂O₂Si
• Molecular Weight: 320.547
• Mol file: 121012-22-4.mol

Synonyms:(E,2R)-1-(Benzyloxy)-2-methyl-5-(tert-butyldimethylsiloxy)-3-pentene

Chemical Property of (E,2R)-1-(Benzyloxy)-2-methyl-5-(tert-butyldimethylsiloxy)-3-pentene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E,2R)-1-(Benzyloxy)-2-methyl-5-(tert-butyldimethylsiloxy)-3-pentene

There total 3 articles about (E,2R)-1-(Benzyloxy)-2-methyl-5-(tert-butyldimethylsiloxy)-3-pentene 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:

(E)-(R)-5-(tert-Butyl-dimethyl-silanyloxy)-2-methyl-pent-3-enoic acid ethyl ester (121012-16-6) → (E,2R)-1-(Benzyloxy)-2-methyl-5-(tert-butyldimethylsiloxy)-3-pentene (121012-22-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 91 percent / LiAlH₄ / diethyl ether / 2 h / 0 °C

2: 1.) NaH / 1.) DMF, 2.) room temp., 5 h

With lithium aluminium tetrahydride; sodium hydride; In diethyl ether;

DOI:10.1021/ja00195a045

Reference yield:

(E)-(R)-5-(tert-Butyl-dimethyl-silanyloxy)-4-methanesulfonyloxy-pent-2-enoic acid ethyl ester (121012-13-3) → (E,2R)-1-(Benzyloxy)-2-methyl-5-(tert-butyldimethylsiloxy)-3-pentene (121012-22-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) CuCN, LiBr, BF₃*Et₂O / 1.) THF, Et₂O, 2.) THF, -78 deg C, 30 min

2: 91 percent / LiAlH₄ / diethyl ether / 2 h / 0 °C

3: 1.) NaH / 1.) DMF, 2.) room temp., 5 h

With lithium aluminium tetrahydride; boron trifluoride diethyl etherate; sodium hydride; lithium bromide; In diethyl ether;

DOI:10.1021/ja00195a045

Reference yield:

benzyl bromide (100-39-0) + (E,2R)-2-Methyl-5-(tert-butyldimethylsiloxy)pent-3-en-1-ol (121012-21-3) → (E,2R)-1-(Benzyloxy)-2-methyl-5-(tert-butyldimethylsiloxy)-3-pentene (121012-22-4)

Guidance literature:

With sodium hydride; Yield given. Multistep reaction; 1.) DMF, 2.) room temp., 5 h;

DOI:10.1021/ja00195a045

upstream raw materials:

benzyl bromide

(E,2R)-2-Methyl-5-(tert-butyldimethylsiloxy)pent-3-en-1-ol

(E)-(R)-5-(tert-Butyl-dimethyl-silanyloxy)-2-methyl-pent-3-enoic acid ethyl ester

(E)-(R)-5-(tert-Butyl-dimethyl-silanyloxy)-4-methanesulfonyloxy-pent-2-enoic acid ethyl ester

Downstream raw materials:

(2E,4R)-5-(benzyloxy)-4-methyl-2-penten-1-ol