(3R,4R,5S,4'R)-4-[carboxyl-(4-diphenylmethyl-2-oxazolidinon-3-yl)]-3-methyl-5-tridecyl-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-tridecyl-4,5-dihydro-2(3H)-furanone
CAS No.:187929-11-9
Molecular Formula:C₃₅H₄₇NO₅
Molecular Weight:561.762
Hs Code.:

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

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

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Technology Process of (3R,4R,5S,4'R)-4-[carboxyl-(4-diphenylmethyl-2-oxazolidinon-3-yl)]-3-methyl-5-tridecyl-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-tridecyl-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: 65.0%

: 124-25-4,511542-15-7
myristylaldehyde

: 187929-09-5
(4R,3'R)-3-(3-ethoxycarbonyl-1-butanoyl)-4-diphenylmethyl-2-oxazolidinone

: 187929-11-9
(3R,4R,5S,4'R)-4-[carboxyl-(4-diphenylmethyl-2-oxazolidinon-3-yl)]-3-methyl-5-tridecyl-4,5-dihydro-2(3H)-furanone

Guidance literature:: With di-n-butylboryl trifluoromethanesulfonate; triethylamine; In dichloromethane; at -78 - 0 ℃; for 12h;
DOI:10.1002/anie.199702741

Reference yield:

: 187929-04-0
(E)-(4R)-3-(3-ethoxycarbonyl-2-propenoyl)-4-diphenyl-methyl-2-oxazolidinone

: 187929-11-9
(3R,4R,5S,4'R)-4-[carboxyl-(4-diphenylmethyl-2-oxazolidinon-3-yl)]-3-methyl-5-tridecyl-4,5-dihydro-2(3H)-furanone

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 / 0 °C

3.2: 65 percent / CH₂Cl₂ / -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:

: 173604-33-6,312624-01-4
(4R)-4-(diphenylmethyl)-2-oxazolidinone

: 187929-11-9
(3R,4R,5S,4'R)-4-[carboxyl-(4-diphenylmethyl-2-oxazolidinon-3-yl)]-3-methyl-5-tridecyl-4,5-dihydro-2(3H)-furanone

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 / 0 °C

4.2: 65 percent / CH₂Cl₂ / -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