(3R,4R,5S,4'R)-4-[carboxyl-(4-diphenylmethyl-2-oxazolidinon-3-yl)]-3-methyl-5-undecyl-4,5-dihydro-2(3H)-furanone

Base Information

• Chemical Name: (3R,4R,5S,4'R)-4-[carboxyl-(4-diphenylmethyl-2-oxazolidinon-3-yl)]-3-methyl-5-undecyl-4,5-dihydro-2(3H)-furanone
• CAS No.: 187929-10-8
• Molecular Formula: C₃₃H₄₃NO₅
• Molecular Weight: 533.708
• Mol file: 187929-10-8.mol

Synonyms:(3R,4R,5S,4'R)-4-[carboxyl-(4-diphenylmethyl-2-oxazolidinon-3-yl)]-3-methyl-5-undecyl-4,5-dihydro-2(3H)-furanone

Chemical Property of (3R,4R,5S,4'R)-4-[carboxyl-(4-diphenylmethyl-2-oxazolidinon-3-yl)]-3-methyl-5-undecyl-4,5-dihydro-2(3H)-furanone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3R,4R,5S,4'R)-4-[carboxyl-(4-diphenylmethyl-2-oxazolidinon-3-yl)]-3-methyl-5-undecyl-4,5-dihydro-2(3H)-furanone

There total 4 articles about (3R,4R,5S,4'R)-4-[carboxyl-(4-diphenylmethyl-2-oxazolidinon-3-yl)]-3-methyl-5-undecyl-4,5-dihydro-2(3H)-furanone 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: 84.0%

Dodecanal (112-54-9) + (4R,3'R)-3-(3-ethoxycarbonyl-1-butanoyl)-4-diphenylmethyl-2-oxazolidinone (187929-09-5) → (3R,4R,5S,4'R)-4-[carboxyl-(4-diphenylmethyl-2-oxazolidinon-3-yl)]-3-methyl-5-undecyl-4,5-dihydro-2(3H)-furanone (187929-10-8)

Guidance literature:

With di-n-butylboryl trifluoromethanesulfonate; triethylamine; In dichloromethane; at -78 - 0 ℃; for 12h;

DOI:10.1002/anie.199702741

Reference yield:

(E)-(4R)-3-(3-ethoxycarbonyl-2-propenoyl)-4-diphenyl-methyl-2-oxazolidinone (187929-04-0) → (3R,4R,5S,4'R)-4-[carboxyl-(4-diphenylmethyl-2-oxazolidinon-3-yl)]-3-methyl-5-undecyl-4,5-dihydro-2(3H)-furanone (187929-10-8)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 91 percent / Bu₃SnH; samarium triflate; Et₃B / O₂ / CH₂Cl₂; tetrahydrofuran; hexane / 1 h / -78 °C

2.1: 76 percent / Bu₃SnH; AIBN / toluene / 12 h / Heating

3.1: dibutylboron triflate; triethylamine / CH₂Cl₂ / 1 h / 0 °C

3.2: 84 percent / CH₂Cl₂ / 10 h / -10 °C

With samarium(II) triflate; 2,2'-azobis(isobutyronitrile); triethyl borane; di-n-butylboryl trifluoromethanesulfonate; tri-n-butyl-tin hydride; triethylamine; oxygen; In tetrahydrofuran; hexane; dichloromethane; toluene;

DOI:10.1021/jo015501x

Reference yield:

(4R)-4-(diphenylmethyl)-2-oxazolidinone (173604-33-6,312624-01-4) → (3R,4R,5S,4'R)-4-[carboxyl-(4-diphenylmethyl-2-oxazolidinon-3-yl)]-3-methyl-5-undecyl-4,5-dihydro-2(3H)-furanone (187929-10-8)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 87 percent / n-BuLi / tetrahydrofuran; hexane / 1 h / -78 °C

2.1: 91 percent / Bu₃SnH; samarium triflate; Et₃B / O₂ / CH₂Cl₂; tetrahydrofuran; hexane / 1 h / -78 °C

3.1: 76 percent / Bu₃SnH; AIBN / toluene / 12 h / Heating

4.1: dibutylboron triflate; triethylamine / CH₂Cl₂ / 1 h / 0 °C

4.2: 84 percent / CH₂Cl₂ / 10 h / -10 °C

With n-butyllithium; samarium(II) triflate; 2,2'-azobis(isobutyronitrile); triethyl borane; di-n-butylboryl trifluoromethanesulfonate; tri-n-butyl-tin hydride; triethylamine; oxygen; In tetrahydrofuran; hexane; dichloromethane; toluene;

DOI:10.1021/jo015501x

upstream raw materials:

Dodecanal

(4R,3'R)-3-(3-ethoxycarbonyl-1-butanoyl)-4-diphenylmethyl-2-oxazolidinone

(4R)-4-(diphenylmethyl)-2-oxazolidinone

(E)-(4R)-3-(3-ethoxycarbonyl-2-propenoyl)-4-diphenyl-methyl-2-oxazolidinone