(-)-(4S,E)-Ethyl 3-<(benzyloxycarbonyl)amino>-5-<(ethoxycarbonyl)methylidene>-2-tetrahydrofuranone

Base Information

Chemical Name:(-)-(4S,E)-Ethyl 3-<(benzyloxycarbonyl)amino>-5-<(ethoxycarbonyl)methylidene>-2-tetrahydrofuranone
CAS No.:167280-64-0
Molecular Formula:C₁₆H₁₇NO₆
Molecular Weight:319.314
Hs Code.:

Synonyms:(-)-(4S,E)-Ethyl 3-<(benzyloxycarbonyl)amino>-5-<(ethoxycarbonyl)methylidene>-2-tetrahydrofuranone

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Chemical Property of (-)-(4S,E)-Ethyl 3-<(benzyloxycarbonyl)amino>-5-<(ethoxycarbonyl)methylidene>-2-tetrahydrofuranone

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Technology Process of (-)-(4S,E)-Ethyl 3-<(benzyloxycarbonyl)amino>-5-<(ethoxycarbonyl)methylidene>-2-tetrahydrofuranone

There total 4 articles about (-)-(4S,E)-Ethyl 3-<(benzyloxycarbonyl)amino>-5-<(ethoxycarbonyl)methylidene>-2-tetrahydrofuranone 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%

: 167280-63-9
(+)-(5S)-1-Ethyl-5-<(benzyloxycarbonyl)amino>-3-oxo-2-(triphenylphosphoranylidene)hexanedioate

: 167280-64-0
(-)-(4S,E)-Ethyl 3-<(benzyloxycarbonyl)amino>-5-<(ethoxycarbonyl)methylidene>-2-tetrahydrofuranone

Guidance literature:: In tetrahydrofuran; for 48h; Heating;
DOI:10.1021/jo00110a026

Reference yield:

: 23632-66-8
(4S)-3-benzyloxycarbonyl-4-carboxymethyl-1,3-oxazolidin-5-one

: 167280-64-0
(-)-(4S,E)-Ethyl 3-<(benzyloxycarbonyl)amino>-5-<(ethoxycarbonyl)methylidene>-2-tetrahydrofuranone

Guidance literature:: Multi-step reaction with 4 steps

1: 100 percent / (COCl)2, DMF / CH₂Cl₂ / 1.) 0 deg C, 2 h, 2.) 20 deg C, 16 h

2: 100 percent / CH₂Cl₂ / 1.) 0 deg C, 30 min, 2.) 20 deg C, 30 min

3: 77 percent / 1 N aq. NaOH / methanol / 4 h / 20 °C

4: 82 percent / tetrahydrofuran / 48 h / Heating

With sodium hydroxide; oxalyl dichloride; N,N-dimethyl-formamide; In tetrahydrofuran; methanol; dichloromethane;
DOI:10.1021/jo00110a026

Reference yield:

: 111197-44-5
(4S)-4-(Chloroformyl)methyl-3-[(phenylmethoxy)carbonyl]oxazolidin-5-one

: 167280-64-0
(-)-(4S,E)-Ethyl 3-<(benzyloxycarbonyl)amino>-5-<(ethoxycarbonyl)methylidene>-2-tetrahydrofuranone

Guidance literature:: Multi-step reaction with 3 steps

1: 100 percent / CH₂Cl₂ / 1.) 0 deg C, 30 min, 2.) 20 deg C, 30 min

2: 77 percent / 1 N aq. NaOH / methanol / 4 h / 20 °C

3: 82 percent / tetrahydrofuran / 48 h / Heating

With sodium hydroxide; In tetrahydrofuran; methanol; dichloromethane;
DOI:10.1021/jo00110a026