2-Oxazolidinone, 4-(phenylmethyl)-3-[[(1R,2S,3S,4S)-3-[2-[[tris(1-methylethyl)silyl]oxy]eth yl]bicyclo[2.2.1]hept-5-en-2-yl]carbonyl]-, (4S)-

Base Information

• Chemical Name: 2-Oxazolidinone, 4-(phenylmethyl)-3-[[(1R,2S,3S,4S)-3-[2-[[tris(1-methylethyl)silyl]oxy]eth yl]bicyclo[2.2.1]hept-5-en-2-yl]carbonyl]-, (4S)-
• CAS No.: 878003-16-8
• Molecular Formula: C29H43NO4Si
• Molecular Weight: 497.75
• Mol file: 878003-16-8.mol

Synonyms:

Chemical Property of 2-Oxazolidinone, 4-(phenylmethyl)-3-[[(1R,2S,3S,4S)-3-[2-[[tris(1-methylethyl)silyl]oxy]eth yl]bicyclo[2.2.1]hept-5-en-2-yl]carbonyl]-, (4S)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-Oxazolidinone, 4-(phenylmethyl)-3-[[(1R,2S,3S,4S)-3-[2-[[tris(1-methylethyl)silyl]oxy]eth yl]bicyclo[2.2.1]hept-5-en-2-yl]carbonyl]-, (4S)-

There total 4 articles about 2-Oxazolidinone, 4-(phenylmethyl)-3-[[(1R,2S,3S,4S)-3-[2-[[tris(1-methylethyl)silyl]oxy]eth yl]bicyclo[2.2.1]hept-5-en-2-yl]carbonyl]-, (4S)- 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: 96.0%

4-benzyl-3-(5-triisopropylsilanyloxypent-2-enoyl)oxazolidin-2-one (878003-15-7) + cyclopenta-1,3-diene (542-92-7,25568-84-7,7313-32-8) → 4-benzyl-3-[3-(2-triisopropylsilanyloxyethyl)bicyclo[2.2.1]hept-5-ene-2-carbonyl]oxazolidin-2-one (878003-16-8)

Guidance literature:

With diethylaluminium chloride; In dichloromethane; at -78 ℃;

DOI:10.1016/j.tetlet.2006.03.124

Reference yield:

4-benzyl-3-(5-triisopropylsilanyloxypent-2-enoyl)oxazolidin-2-one (878003-15-7) + cyclopenta-1,3-diene (542-92-7,25568-84-7,7313-32-8) → 4-benzyl-3-[3-(2-triisopropylsilanyloxyethyl)bicyclo[2.2.1]hept-5-ene-2-carbonyl]oxazolidin-2-one (878003-16-8) + (S)-4-Benzyl-3-[(1S,2R,3R,4R)-3-(2-triisopropylsilanyloxy-ethyl)-bicyclo[2.2.1]hept-5-ene-2-carbonyl]-oxazolidin-2-one

Guidance literature:

With diethylaluminium chloride; In dichloromethane; at -78 ℃; for 12h; Title compound not separated from byproducts;

DOI:10.1021/ja057899a

Reference yield:

(S)-3-acryloyl-4-benzyloxazolidin-2-one (90719-27-0) → 4-benzyl-3-[3-(2-triisopropylsilanyloxyethyl)bicyclo[2.2.1]hept-5-ene-2-carbonyl]oxazolidin-2-one (878003-16-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 81 percent / ruthenium-catalyst / CH₂Cl₂ / 45 °C

2: 96 percent / Et₂AlCl / CH₂Cl₂ / -78 °C

With diethylaluminium chloride; ruthenium-catalyst; In dichloromethane; 1: cross metathesis / 2: Diels-Alder reaction;

DOI:10.1016/j.tetlet.2006.03.124

upstream raw materials:

4-benzyl-3-(5-triisopropylsilanyloxypent-2-enoyl)oxazolidin-2-one

cyclopenta-1,3-diene

(S)-3-acryloyl-4-benzyloxazolidin-2-one

1-triisopropylsiloxy-3-butene