5-[2-(benzyloxycarbonyl)amino-2-tert-butoxycarbonyl]ethyl-3-phenyl-3-vinyldihydrobenzo[b]furan-2-one

Base Information

Chemical Name:5-[2-(benzyloxycarbonyl)amino-2-tert-butoxycarbonyl]ethyl-3-phenyl-3-vinyldihydrobenzo[b]furan-2-one
CAS No.:870456-14-7
Molecular Formula:C₃₁H₃₁NO₆
Molecular Weight:513.59
Hs Code.:

Synonyms:5-[2-(benzyloxycarbonyl)amino-2-tert-butoxycarbonyl]ethyl-3-phenyl-3-vinyldihydrobenzo[b]furan-2-one

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Chemical Property of 5-[2-(benzyloxycarbonyl)amino-2-tert-butoxycarbonyl]ethyl-3-phenyl-3-vinyldihydrobenzo[b]furan-2-one

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Technology Process of 5-[2-(benzyloxycarbonyl)amino-2-tert-butoxycarbonyl]ethyl-3-phenyl-3-vinyldihydrobenzo[b]furan-2-one

There total 7 articles about 5-[2-(benzyloxycarbonyl)amino-2-tert-butoxycarbonyl]ethyl-3-phenyl-3-vinyldihydrobenzo[b]furan-2-one 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: 63.0%

: 870456-13-6
N-benzyloxycarbonyl-3-iodo-O-(2-phenylbut-2-enoyl)tyrosine tert-butyl ester

: 870456-14-7
5-[2-(benzyloxycarbonyl)amino-2-tert-butoxycarbonyl]ethyl-3-phenyl-3-vinyldihydrobenzo[b]furan-2-one

Guidance literature:: With silver orthophosphate; (S)-(1,1'-binaphthalene)-2,2'-diylbis(diphenylphosphine); tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; In N,N-dimethyl acetamide; at 100 ℃; for 48h;
DOI:10.1039/b510653b

Reference yield:

: 501-53-1,94274-21-2
benzyl chloroformate

: 870456-14-7
5-[2-(benzyloxycarbonyl)amino-2-tert-butoxycarbonyl]ethyl-3-phenyl-3-vinyldihydrobenzo[b]furan-2-one

Guidance literature:: Multi-step reaction with 4 steps

1: 95 percent / aq. Na₂CO₃ / diethyl ether / 3 h / 25 °C

2: NaI; chloramine T / dimethylsulfoxide / 24 h

3: 74 percent / DCC / CH₂Cl₂ / 2 h / 0 °C

4: 63 percent / Ag₃PO₄; (S)-BINAP / Pd₂(dba)3*CHCl₃ / N,N-dimethyl-acetamide / 48 h / 100 °C

With silver orthophosphate; chloroamine-T; sodium carbonate; (S)-(1,1'-binaphthalene)-2,2'-diylbis(diphenylphosphine); dicyclohexyl-carbodiimide; sodium iodide; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; In diethyl ether; dichloromethane; N,N-dimethyl acetamide; dimethyl sulfoxide; 4: Heck reaction;
DOI:10.1039/b510653b

Reference yield:

: 591-50-4
iodobenzene

: 870456-14-7
5-[2-(benzyloxycarbonyl)amino-2-tert-butoxycarbonyl]ethyl-3-phenyl-3-vinyldihydrobenzo[b]furan-2-one

Guidance literature:: Multi-step reaction with 3 steps

1.1: Bu₃SnH / Pd(PPh₃)4 / tetrahydrofuran / 20 °C

1.2: CuI / Pd(PPh₃)4 / dimethylformamide / 20 °C

1.3: 1.63 g / KOH / ethanol / 24 h / Heating

2.1: 74 percent / DCC / CH₂Cl₂ / 2 h / 0 °C

3.1: 63 percent / Ag₃PO₄; (S)-BINAP / Pd₂(dba)3*CHCl₃ / N,N-dimethyl-acetamide / 48 h / 100 °C

With silver orthophosphate; tri-n-butyl-tin hydride; (S)-(1,1'-binaphthalene)-2,2'-diylbis(diphenylphosphine); dicyclohexyl-carbodiimide; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; dichloromethane; N,N-dimethyl acetamide; 1.2: Stille reaction / 3.1: Heck reaction;
DOI:10.1039/b510653b