(2E,4S)-5-(tert-butyldiphenylsilyloxy)-4-(methoxymethoxy)pent-2-en-1-ol

Base Information

• Chemical Name: (2E,4S)-5-(tert-butyldiphenylsilyloxy)-4-(methoxymethoxy)pent-2-en-1-ol
• CAS No.: 942499-24-3
• Molecular Formula: C₂₃H₃₂O₄Si
• Molecular Weight: 400.59
• Mol file: 942499-24-3.mol

Synonyms:(2E,4S)-5-(tert-butyldiphenylsilyloxy)-4-(methoxymethoxy)pent-2-en-1-ol

Chemical Property of (2E,4S)-5-(tert-butyldiphenylsilyloxy)-4-(methoxymethoxy)pent-2-en-1-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2E,4S)-5-(tert-butyldiphenylsilyloxy)-4-(methoxymethoxy)pent-2-en-1-ol

There total 4 articles about (2E,4S)-5-(tert-butyldiphenylsilyloxy)-4-(methoxymethoxy)pent-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: 86.0%

ethyl (2E,4S)-5-(tert-butyldiphenylsilanyloxy)-4-(methoxymethyloxy)-2-pentenoate (861222-40-4) → (2E,4S)-5-(tert-butyldiphenylsilyloxy)-4-(methoxymethoxy)pent-2-en-1-ol (942499-24-3)

Guidance literature:

With diisobutylaluminium hydride; In diethyl ether; at -78 - 20 ℃;

DOI:10.1016/j.tetlet.2007.03.161

Reference yield:

ethyl (2E,4S)-5-(tert-butyldiphenylsilanyloxy)-4-hydroxy-2-pentenoate (885051-17-2) → (2E,4S)-5-(tert-butyldiphenylsilyloxy)-4-(methoxymethoxy)pent-2-en-1-ol (942499-24-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 86 percent / EtN(i-Pr)2 / CH₂Cl₂

2: 86 percent / DIBAL-H / diethyl ether / -78 - 20 °C

With diisobutylaluminium hydride; N-ethyl-N,N-diisopropylamine; In diethyl ether; dichloromethane;

DOI:10.1016/j.tetlet.2007.03.161

Reference yield:

ethyl (E)-3-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)acrylate (64520-58-7,917877-01-1) → (2E,4S)-5-(tert-butyldiphenylsilyloxy)-4-(methoxymethoxy)pent-2-en-1-ol (942499-24-3)

Guidance literature:

Multi-step reaction with 4 steps

1: 94 percent / aq. HCl

2: 100 percent / imidazole / tetrahydrofuran

3: 86 percent / EtN(i-Pr)2 / CH₂Cl₂

4: 86 percent / DIBAL-H / diethyl ether / -78 - 20 °C

With 1H-imidazole; hydrogenchloride; diisobutylaluminium hydride; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; diethyl ether; dichloromethane;

DOI:10.1016/j.tetlet.2007.03.161

upstream raw materials:

ethyl (2E,4S)-5-(tert-butyldiphenylsilanyloxy)-4-(methoxymethyloxy)-2-pentenoate

ethyl (2E,4S)-5-(tert-butyldiphenylsilanyloxy)-4-hydroxy-2-pentenoate

ethyl (E)-3-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)acrylate

(S)-ethyl trans-4,5-dihydroxylpent-2-enoate

Downstream raw materials:

C₂₅H₃₂Cl₃NO₄Si

(3S,4S)-5-(tert-butyldiphenylsilyloxy)-4-methoxymethoxy-3-(trichloromethylcarbonylamino)pent-1-ene