(2R,5'S)-5'-(4-Azido-butyl)-4-benzyl-5'-(2,2-dimethoxy-ethyl)-2-isopropyl-1,2,1',5'-tetrahydro-[2,3']bipyrrolyl-3,4'-dione

Base Information

Chemical Name:(2R,5'S)-5'-(4-Azido-butyl)-4-benzyl-5'-(2,2-dimethoxy-ethyl)-2-isopropyl-1,2,1',5'-tetrahydro-[2,3']bipyrrolyl-3,4'-dione
CAS No.:847020-43-3
Molecular Formula:C₂₆H₃₅N₅O₄
Molecular Weight:481.595
Hs Code.:

Synonyms:(2R,5'S)-5'-(4-Azido-butyl)-4-benzyl-5'-(2,2-dimethoxy-ethyl)-2-isopropyl-1,2,1',5'-tetrahydro-[2,3']bipyrrolyl-3,4'-dione

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Chemical Property of (2R,5'S)-5'-(4-Azido-butyl)-4-benzyl-5'-(2,2-dimethoxy-ethyl)-2-isopropyl-1,2,1',5'-tetrahydro-[2,3']bipyrrolyl-3,4'-dione

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Technology Process of (2R,5'S)-5'-(4-Azido-butyl)-4-benzyl-5'-(2,2-dimethoxy-ethyl)-2-isopropyl-1,2,1',5'-tetrahydro-[2,3']bipyrrolyl-3,4'-dione

There total 19 articles about (2R,5'S)-5'-(4-Azido-butyl)-4-benzyl-5'-(2,2-dimethoxy-ethyl)-2-isopropyl-1,2,1',5'-tetrahydro-[2,3']bipyrrolyl-3,4'-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:

: (S)-6-Azido-2-[2-((S)-4-benzyl-2-isopropyl-3-oxo-2,3-dihydro-1H-pyrrol-2-yl)-eth-(E)-ylideneamino]-2-(2,2-dimethoxy-ethyl)-hexanoic acid methyl ester

: 847020-43-3
(2R,5'S)-5'-(4-Azido-butyl)-4-benzyl-5'-(2,2-dimethoxy-ethyl)-2-isopropyl-1,2,1',5'-tetrahydro-[2,3']bipyrrolyl-3,4'-dione

Guidance literature:: With potassium hexamethylsilazane; In tetrahydrofuran; toluene; at 20 ℃; for 0.25h;
DOI:10.1021/ol0476974

Reference yield:

: 72-18-4,25609-85-2,7004-03-7,921-10-8
L-valine

: 847020-43-3
(2R,5'S)-5'-(4-Azido-butyl)-4-benzyl-5'-(2,2-dimethoxy-ethyl)-2-isopropyl-1,2,1',5'-tetrahydro-[2,3']bipyrrolyl-3,4'-dione

Guidance literature:: Multi-step reaction with 14 steps

1.1: NaOH / ethanol; H₂O / 2 h / 20 °C

1.2: pentane / 72 h / 45 °C

1.3: 85 percent / CH₂Cl₂ / 384 h / 5 °C

2.1: KHMDS / toluene; tetrahydrofuran / 0.25 h / -78 °C

2.2: 89 percent / tetrahydrofuran; toluene / 0.75 h / -78 °C

3.1: aq. KOH / methanol / 16 h / Heating

4.1: 76 percent / K₂CO₃ / dimethylformamide / 0 - 20 °C

5.1: 93 percent / dimedone; Pd(Ph₃P)4 / tetrahydrofuran / 16 h

6.1: 96 percent / diisopropylethylamine / tetrahydrofuran / 0 - 20 °C

7.1: O₃ / CH₂Cl₂ / -78 °C

7.2: 99 percent / Ph₃P / CH₂Cl₂ / 4 h / -78 - 20 °C

8.1: 99 percent / p-TsOH / methanol / 1.5 h / Heating

9.1: 97 percent / cyclohexene / Pd/C / ethanol / 2.5 h / Heating

10.1: benzene

11.1: 4.50 g / KHMDS / tetrahydrofuran; toluene / 0.25 h / 20 °C

12.1: 95 percent / p-toluenesulfonic acid / tetrahydrofuran; H₂O / 5 h / 40 °C

13.1: benzene / 2 h / 60 °C

14.1: 1.50 g / KHMDS / tetrahydrofuran; toluene / 0.25 h / 20 °C

With potassium hydroxide; sodium hydroxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium hexamethylsilazane; potassium carbonate; dimedone; toluene-4-sulfonic acid; ozone; N-ethyl-N,N-diisopropylamine; cyclohexene; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; N,N-dimethyl-formamide; toluene; benzene;
DOI:10.1021/ol0476974

Reference yield:

: 182149-08-2
(2S,4S)-2-tert-Butyl-4-isopropyl-5-oxo-oxazolidine-3-carboxylic acid allyl ester

: 847020-43-3
(2R,5'S)-5'-(4-Azido-butyl)-4-benzyl-5'-(2,2-dimethoxy-ethyl)-2-isopropyl-1,2,1',5'-tetrahydro-[2,3']bipyrrolyl-3,4'-dione

Guidance literature:: Multi-step reaction with 13 steps

1.1: KHMDS / toluene; tetrahydrofuran / 0.25 h / -78 °C

1.2: 89 percent / tetrahydrofuran; toluene / 0.75 h / -78 °C

2.1: aq. KOH / methanol / 16 h / Heating

3.1: 76 percent / K₂CO₃ / dimethylformamide / 0 - 20 °C

4.1: 93 percent / dimedone; Pd(Ph₃P)4 / tetrahydrofuran / 16 h

5.1: 96 percent / diisopropylethylamine / tetrahydrofuran / 0 - 20 °C

6.1: O₃ / CH₂Cl₂ / -78 °C

6.2: 99 percent / Ph₃P / CH₂Cl₂ / 4 h / -78 - 20 °C

7.1: 99 percent / p-TsOH / methanol / 1.5 h / Heating

8.1: 97 percent / cyclohexene / Pd/C / ethanol / 2.5 h / Heating

9.1: benzene

10.1: 4.50 g / KHMDS / tetrahydrofuran; toluene / 0.25 h / 20 °C

11.1: 95 percent / p-toluenesulfonic acid / tetrahydrofuran; H₂O / 5 h / 40 °C

12.1: benzene / 2 h / 60 °C

13.1: 1.50 g / KHMDS / tetrahydrofuran; toluene / 0.25 h / 20 °C

With potassium hydroxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium hexamethylsilazane; potassium carbonate; dimedone; toluene-4-sulfonic acid; ozone; N-ethyl-N,N-diisopropylamine; cyclohexene; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; N,N-dimethyl-formamide; toluene; benzene;
DOI:10.1021/ol0476974