2-[(S)-1-Benzyl-2-oxo-3-(tetrahydro-pyran-2-yloxy)-propyl]-isoindole-1,3-dione

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Chemical Name:2-[(S)-1-Benzyl-2-oxo-3-(tetrahydro-pyran-2-yloxy)-propyl]-isoindole-1,3-dione
CAS No.:1026632-96-1
Molecular Formula:C₂₃H₂₃NO₅
Molecular Weight:393.439
Hs Code.:

Synonyms:2-[(S)-1-Benzyl-2-oxo-3-(tetrahydro-pyran-2-yloxy)-propyl]-isoindole-1,3-dione

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Chemical Property of 2-[(S)-1-Benzyl-2-oxo-3-(tetrahydro-pyran-2-yloxy)-propyl]-isoindole-1,3-dione

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Technology Process of 2-[(S)-1-Benzyl-2-oxo-3-(tetrahydro-pyran-2-yloxy)-propyl]-isoindole-1,3-dione

There total 1 articles about 2-[(S)-1-Benzyl-2-oxo-3-(tetrahydro-pyran-2-yloxy)-propyl]-isoindole-1,3-dione 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:

: 32150-91-7
phthaloyl-L-phenylalanyl chloride

: 1026632-96-1
2-[(S)-1-Benzyl-2-oxo-3-(tetrahydro-pyran-2-yloxy)-propyl]-isoindole-1,3-dione

Guidance literature:: Multi-step reaction with 2 steps

1: 2.) 0.6 M aq. HCl / 1.) 95 to 100 deg C, 4 h, 2.) dioxane, 80 to 85 deg C, 30 min

2: TsOH*H₂O / CH₂Cl₂ / 16 h / 20 °C

With hydrogenchloride; toluene-4-sulfonic acid; In dichloromethane;
DOI:10.1021/jo00092a026

Reference yield:

: 1026632-96-1
2-[(S)-1-Benzyl-2-oxo-3-(tetrahydro-pyran-2-yloxy)-propyl]-isoindole-1,3-dione

: 127779-20-8,128053-46-3,137622-85-6,147922-51-8,147922-52-9
Saquinavir

Guidance literature:: Multi-step reaction with 9 steps

1: NaBH₄ / tetrahydrofuran; H₂O / 0.25 h / 0 °C

2: pyridine / 16 h / 20 °C

3: TsOH*H₂O / ethanol / 1.) 20 deg C, 1 h, 2.) 4 deg C, overnight

4: 69 percent / t-BuOK / dimethylformamide / 1 h / 20 °C

5: 80 percent / dimethylformamide / 8.5 h / 120 °C

6: 1.) 33percent MeNH₂, 2.) 4 M HCl / 1.) EtOH, r.t., 1 h, 2.) EtOH, EtOAc, r.t., overnight

7: 48 percent / 1-hydroxybenzotriazole hydrate, dicyclohexylcarbodiimide, N-ethylmorpholine / tetrahydrofuran / 64 h / Ambient temperature

8: H₂ / 10percent Pd/C / ethanol / 16 h

9: 1-hydroxybenzotriazole hydrate, dicyclohexylcarbodiimide, N-ethylmorpholine / tetrahydrofuran / 16 h / Ambient temperature

With N-ethylmorpholine;; pyridine; hydrogenchloride; sodium tetrahydroborate; potassium tert-butylate; hydrogen; toluene-4-sulfonic acid; 1-hydroxybenzotriazol-hydrate; dicyclohexyl-carbodiimide; methylamine; palladium on activated charcoal; In tetrahydrofuran; ethanol; water; N,N-dimethyl-formamide;
DOI:10.1021/jo00092a026