ethyl(R,E)-6-<(tert-butyldiphenylsilyl)oxy>-5-fluoro-2-hexenoate

Base Information

• Chemical Name: ethyl(R,E)-6-<(tert-butyldiphenylsilyl)oxy>-5-fluoro-2-hexenoate
• CAS No.: 114837-21-7
• Molecular Formula: C₂₄H₃₁FO₃Si
• Molecular Weight: 414.592
• Mol file: 114837-21-7.mol

Synonyms:ethyl(R,E)-6-<(tert-butyldiphenylsilyl)oxy>-5-fluoro-2-hexenoate

Chemical Property of ethyl(R,E)-6-<(tert-butyldiphenylsilyl)oxy>-5-fluoro-2-hexenoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ethyl(R,E)-6-<(tert-butyldiphenylsilyl)oxy>-5-fluoro-2-hexenoate

There total 4 articles about ethyl(R,E)-6-<(tert-butyldiphenylsilyl)oxy>-5-fluoro-2-hexenoate 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: 36.0%

ethyl 6-<(tert-butyldiphenylsilyl)oxy>-5(S,E)-hydroxy-2-hexenoate (96720-09-1) → ethyl(R,E)-6-<(tert-butyldiphenylsilyl)oxy>-5-fluoro-2-hexenoate (114837-21-7)

Guidance literature:

With 4,4'-diaminostilbene-2,2'-disulfonic acid; In various solvent(s); at -105 - -80 ℃; for 0.333333h;

DOI:10.1021/ja00222a008

Reference yield:

(E)-ethyl 4-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)but-2-enoate (96720-07-9) → ethyl(R,E)-6-<(tert-butyldiphenylsilyl)oxy>-5-fluoro-2-hexenoate (114837-21-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 93 percent / 1 N HCl / tetrahydrofuran / 18 h / Ambient temperature

2: 66 percent / imidazol, / dimethylformamide / 0.17 h

3: 36 percent / DAST / various solvent(s) / 0.33 h / -105 - -80 °C

With 1H-imidazole; hydrogenchloride; 4,4'-diaminostilbene-2,2'-disulfonic acid; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1021/ja00222a008

Reference yield:

ethyl (S,E)-5,6-dihydroxy-2-hexenoate (96720-08-0) → ethyl(R,E)-6-<(tert-butyldiphenylsilyl)oxy>-5-fluoro-2-hexenoate (114837-21-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 66 percent / imidazol, / dimethylformamide / 0.17 h

2: 36 percent / DAST / various solvent(s) / 0.33 h / -105 - -80 °C

With 1H-imidazole; 4,4'-diaminostilbene-2,2'-disulfonic acid; In N,N-dimethyl-formamide;

DOI:10.1021/ja00222a008

upstream raw materials:

ethyl 6-<(tert-butyldiphenylsilyl)oxy>-5(S,E)-hydroxy-2-hexenoate

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

ethyl (S,E)-5,6-dihydroxy-2-hexenoate

tert-butylchlorodiphenylsilane

Downstream raw materials:

trans-5-(ethoxycarbonyl)penta-2,4-dien-1-ol

(E)-5-Fluoro-6-hydroxy-hex-2-enoic acid ethyl ester