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

Base Information

• Chemical Name: ethyl (2E,4S)-5-(tert-butyldiphenylsilanyloxy)-4-hydroxy-2-pentenoate
• CAS No.: 885051-17-2
• Molecular Formula: C₂₃H₃₀O₄Si
• Molecular Weight: 398.574
• Mol file: 885051-17-2.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 2 articles about ethyl (2E,4S)-5-(tert-butyldiphenylsilanyloxy)-4-hydroxy-2-pentenoate 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:

ethyl (E)-3-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)acrylate (64520-58-7,917877-01-1) → ethyl (2E,4S)-5-(tert-butyldiphenylsilanyloxy)-4-hydroxy-2-pentenoate (885051-17-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 94 percent / aq. HCl

2: 100 percent / imidazole / tetrahydrofuran

With 1H-imidazole; hydrogenchloride; In tetrahydrofuran;

DOI:10.1016/j.tetlet.2007.03.161

Reference yield:

ethyl (2'S)-3-(1',4'-dioxa-spiro[4.5]dec-2'-yl)-acrylate (112980-46-8) → ethyl (2E,4S)-5-(tert-butyldiphenylsilanyloxy)-4-hydroxy-2-pentenoate (885051-17-2)

Guidance literature:

Multi-step reaction with 2 steps

1: acetic acid / water / 4 h / 20 - 80 °C

2: 1H-imidazole; dmap / N,N-dimethyl-formamide / 16 h / 0 - 20 °C / Inert atmosphere

With 1H-imidazole; dmap; acetic acid; In water; N,N-dimethyl-formamide;

DOI:10.1002/chem.201102462

Reference yield: 86.0%

ethyl (2E,4S)-5-(tert-butyldiphenylsilanyloxy)-4-hydroxy-2-pentenoate (885051-17-2) + chloromethyl methyl ether (107-30-2) → ethyl (2E,4S)-5-(tert-butyldiphenylsilanyloxy)-4-(methoxymethyloxy)-2-pentenoate (861222-40-4)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In dichloromethane; Heating;

DOI:10.1016/j.tet.2008.07.062

upstream raw materials:

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

ethyl (2'S)-3-(1',4'-dioxa-spiro[4.5]dec-2'-yl)-acrylate

Downstream raw materials:

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

C₂₅H₃₂Cl₃NO₄Si

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

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