(+/-)-(E)-1-benzyloxy-4-hydroxy-5-(tert-butyldimethylsilyloxy)pent-2-ene

Base Information

• Chemical Name: (+/-)-(E)-1-benzyloxy-4-hydroxy-5-(tert-butyldimethylsilyloxy)pent-2-ene
• CAS No.: 608530-24-1
• Molecular Formula: C₁₈H₃₀O₃Si
• Molecular Weight: 322.52
• Mol file: 608530-24-1.mol

Synonyms:(+/-)-(E)-1-benzyloxy-4-hydroxy-5-(tert-butyldimethylsilyloxy)pent-2-ene

Chemical Property of (+/-)-(E)-1-benzyloxy-4-hydroxy-5-(tert-butyldimethylsilyloxy)pent-2-ene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (+/-)-(E)-1-benzyloxy-4-hydroxy-5-(tert-butyldimethylsilyloxy)pent-2-ene

There total 4 articles about (+/-)-(E)-1-benzyloxy-4-hydroxy-5-(tert-butyldimethylsilyloxy)pent-2-ene 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: 92.0%

tert-butyldimethylsilyl chloride (18162-48-6) + (+/-)-1-benzyloxy-4,5-dihydroxy-pent-2-ene (608530-23-0) → (+/-)-(E)-1-benzyloxy-4-hydroxy-5-(tert-butyldimethylsilyloxy)pent-2-ene (608530-24-1)

Guidance literature:

With 1H-imidazole; In dichloromethane; at -10 ℃; for 0.5h;

DOI:10.1016/S0040-4020(03)00986-4

Reference yield:

(E)-1-benzyloxy-(4,5-O-isopropylidene)pent-2-ene (608530-22-9) → (+/-)-(E)-1-benzyloxy-4-hydroxy-5-(tert-butyldimethylsilyloxy)pent-2-ene (608530-24-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 95 percent / HCl / H₂O / 2 h / 20 °C

2: 92 percent / imidazole / CH₂Cl₂ / 0.5 h / -10 °C

With 1H-imidazole; hydrogenchloride; In dichloromethane; water;

DOI:10.1016/S0040-4020(03)00986-4

Reference yield:

(±)-ethyl trans-3-(2,2-dimethyl-1,3-dioxolan-4-yl)propenoate (128525-69-9,917877-01-1) → (+/-)-(E)-1-benzyloxy-4-hydroxy-5-(tert-butyldimethylsilyloxy)pent-2-ene (608530-24-1)

Guidance literature:

Multi-step reaction with 4 steps

1: 85 percent / DIBAL-H / CH₂Cl₂ / -78 °C

2: 94 percent / NaH / tetrahydrofuran

3: TFA; H₂O / 1 h / 20 °C

4: Et₃N / CH₂Cl₂ / 5 h / 0 °C

With water; sodium hydride; diisobutylaluminium hydride; triethylamine; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; 1: Reduction / 2: Etherification / 3: Hydrolysis / 4: Etherification;

upstream raw materials:

tert-butyldimethylsilyl chloride

(+/-)-1-benzyloxy-4,5-dihydroxy-pent-2-ene

(E)-1-benzyloxy-(4,5-O-isopropylidene)pent-2-ene

(±)-ethyl trans-3-(2,2-dimethyl-1,3-dioxolan-4-yl)propenoate

Downstream raw materials:

[(2E,4Z)-4,5-Bis-(tert-butyl-dimethyl-silanyloxy)-penta-2,4-dienyloxymethyl]-benzene

(+/-)-(E)-1-benzyloxy-4-O-(benzylglycoloyloxy)-5-(tert-butyldimethylsilyloxy)pent-2-ene