3-(4-nitrophenylcarbonyloxy)-5-phenylmethyl-(3S,5S)-tetrahydrofuran-2-one

Base Information

Chemical Name:3-(4-nitrophenylcarbonyloxy)-5-phenylmethyl-(3S,5S)-tetrahydrofuran-2-one
CAS No.:321868-63-7
Molecular Formula:C₁₈H₁₅NO₆
Molecular Weight:341.32
Hs Code.:

Synonyms:3-(4-nitrophenylcarbonyloxy)-5-phenylmethyl-(3S,5S)-tetrahydrofuran-2-one

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Chemical Property of 3-(4-nitrophenylcarbonyloxy)-5-phenylmethyl-(3S,5S)-tetrahydrofuran-2-one

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Technology Process of 3-(4-nitrophenylcarbonyloxy)-5-phenylmethyl-(3S,5S)-tetrahydrofuran-2-one

There total 7 articles about 3-(4-nitrophenylcarbonyloxy)-5-phenylmethyl-(3S,5S)-tetrahydrofuran-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: 80.0%

: 321868-48-8
3-hydroxy-5-phenylmethyl-(3R,5S)-tetrahydrofuran-2-one

: 62-23-7
4-nitro-benzoic acid

: 321868-63-7
3-(4-nitrophenylcarbonyloxy)-5-phenylmethyl-(3S,5S)-tetrahydrofuran-2-one

Guidance literature:: With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; at 20 ℃; for 8h;
DOI:10.1016/S0957-4166(00)00389-X

Reference yield:

: 14260-67-4
(3aR,5R,6aR)-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxole-5-carbaldehyde

: 321868-63-7
3-(4-nitrophenylcarbonyloxy)-5-phenylmethyl-(3S,5S)-tetrahydrofuran-2-one

Guidance literature:: Multi-step reaction with 6 steps

1.1: tetrahydrofuran / 4.33 h / 0 °C

2.1: NaH / tetrahydrofuran; hexane / 0.25 h / 0 °C

2.2: tetrahydrofuran; hexane / 0.25 h / 0 °C

2.3: 95 percent / tetrahydrofuran; hexane / 0 - 20 °C

3.1: 79 percent / nBu₃SnH; AIBN / toluene / 6 h / Heating

4.1: 82 percent / aq. AcOH; H₂SO₄ / 6 h / 45 °C

5.1: 66 percent / Ag₂CO₃-Celite / benzene; dimethylformamide / 3 h / Heating

6.1: 80 percent / Ph₃P; DEAD / tetrahydrofuran / 8 h / 20 °C

With 2,2'-azobis(isobutyronitrile); sulfuric acid; tri-n-butyl-tin hydride; sodium hydride; acetic acid; triphenylphosphine; silver carbonate; diethylazodicarboxylate; In tetrahydrofuran; hexane; N,N-dimethyl-formamide; toluene; benzene; 1.1: Addition / 2.1: Metallation / 2.2: Addition / 2.3: Methylation / 3.1: deoxygenation / 4.1: Hydrolysis / 5.1: Oxidation / 6.1: Mitsunobu reaction;
DOI:10.1016/S0957-4166(00)00389-X

Reference yield:

: 4005-46-3
(1R)-1-[(3aR,5R,6aR)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl]ethane-1,2-diol

: 321868-63-7
3-(4-nitrophenylcarbonyloxy)-5-phenylmethyl-(3S,5S)-tetrahydrofuran-2-one

Guidance literature:: Multi-step reaction with 7 steps

1.1: aq. NaHCO₃; NaIO₄ / CH₂Cl₂; methanol / 2 h / 20 °C

2.1: tetrahydrofuran / 4.33 h / 0 °C

3.1: NaH / tetrahydrofuran; hexane / 0.25 h / 0 °C

3.2: tetrahydrofuran; hexane / 0.25 h / 0 °C

3.3: 95 percent / tetrahydrofuran; hexane / 0 - 20 °C

4.1: 79 percent / nBu₃SnH; AIBN / toluene / 6 h / Heating

5.1: 82 percent / aq. AcOH; H₂SO₄ / 6 h / 45 °C

6.1: 66 percent / Ag₂CO₃-Celite / benzene; dimethylformamide / 3 h / Heating

7.1: 80 percent / Ph₃P; DEAD / tetrahydrofuran / 8 h / 20 °C

With sodium periodate; 2,2'-azobis(isobutyronitrile); sulfuric acid; tri-n-butyl-tin hydride; sodium hydride; sodium hydrogencarbonate; acetic acid; triphenylphosphine; silver carbonate; diethylazodicarboxylate; In tetrahydrofuran; methanol; hexane; dichloromethane; N,N-dimethyl-formamide; toluene; benzene; 1.1: oxidative cleavage / 2.1: Addition / 3.1: Metallation / 3.2: Addition / 3.3: Methylation / 4.1: deoxygenation / 5.1: Hydrolysis / 6.1: Oxidation / 7.1: Mitsunobu reaction;
DOI:10.1016/S0957-4166(00)00389-X