(R,Z)-ethyl 4-(tert-butyldiphenylsilyloxy)hept-2-enoate

Base Information

• Chemical Name: (R,Z)-ethyl 4-(tert-butyldiphenylsilyloxy)hept-2-enoate
• CAS No.: 1359984-28-3
• Molecular Formula: C₂₅H₃₄O₃Si
• Molecular Weight: 410.629
• Mol file: 1359984-28-3.mol

Synonyms:(R,Z)-ethyl 4-(tert-butyldiphenylsilyloxy)hept-2-enoate

Chemical Property of (R,Z)-ethyl 4-(tert-butyldiphenylsilyloxy)hept-2-enoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R,Z)-ethyl 4-(tert-butyldiphenylsilyloxy)hept-2-enoate

There total 2 articles about (R,Z)-ethyl 4-(tert-butyldiphenylsilyloxy)hept-2-enoate 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: 82.0%

(R)-(+)-2-(tert-Butyldiphenylsilyloxy)pentanal + ethyl diphenylphosphonoacetate (16139-79-0) → (R,Z)-ethyl 4-(tert-butyldiphenylsilyloxy)hept-2-enoate (1359984-28-3)

Guidance literature:

ethyl diphenylphosphonoacetate; With sodium hydride; In tetrahydrofuran; mineral oil; at 0 ℃; for 0.25h;

(R)-(+)-2-(tert-Butyldiphenylsilyloxy)pentanal; In tetrahydrofuran; mineral oil; at 0 ℃; optical yield given as %de; stereoselective reaction;

DOI:10.1016/j.tetlet.2011.12.119

Reference yield:

(R)-(+)-2-hydroxypentanenitrile (10021-63-3) → (R,Z)-ethyl 4-(tert-butyldiphenylsilyloxy)hept-2-enoate (1359984-28-3)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 1H-imidazole; dmap / 12 h

2.1: diisobutylaluminium hydride / dichloromethane / -78 °C

3.1: sodium hydride / tetrahydrofuran; mineral oil / 0.25 h / 0 °C

3.2: 0 °C

With 1H-imidazole; dmap; sodium hydride; diisobutylaluminium hydride; In tetrahydrofuran; dichloromethane; mineral oil; 3.1: Horner-Wadsworth-Emmons olefination / 3.2: Horner-Wadsworth-Emmons olefination;

DOI:10.1016/j.tetlet.2011.12.119

Reference yield: 79.0%

(R,Z)-ethyl 4-(tert-butyldiphenylsilyloxy)hept-2-enoate (1359984-28-3) → (2R,3S,4R)-ethyl 4-(tert-butyldiphenylsilyloxy)-2,3-dihydroxyheptanoate (1359984-30-7)

Guidance literature:

With methanesulfonamide; AD-mix β; water; In tert-butyl alcohol; at 20 ℃; for 24h;

DOI:10.1016/j.tetlet.2011.12.119

upstream raw materials:

(R)-(+)-2-hydroxypentanenitrile

ethyl diphenylphosphonoacetate

Downstream raw materials:

(2R,3S,4R)-ethyl 4-(tert-butyldiphenylsilyloxy)-2,3-dihydroxyheptanoate

C₂₈H₄₀O₅Si

C₂₆H₃₆O₄Si

C₂₇H₃₈O₃Si