(4S,5S)-4-Benzyl-5-[(2S,5'S)-5'-benzyl-4-((R)-1-tert-butylcarbamoyl-2-phenyl-ethyl)-2-isobutyl-3,4'-dioxo-2,3,4',5'-tetrahydro-1H,1'H-[2,3']bipyrrolyl-5'-ylmethyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

Base Information

• Chemical Name: (4S,5S)-4-Benzyl-5-[(2S,5'S)-5'-benzyl-4-((R)-1-tert-butylcarbamoyl-2-phenyl-ethyl)-2-isobutyl-3,4'-dioxo-2,3,4',5'-tetrahydro-1H,1'H-[2,3']bipyrrolyl-5'-ylmethyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester
• CAS No.: 173092-09-6
• Molecular Formula: C₅₀H₆₄N₄O₆
• Molecular Weight: 817.081

Synonyms:(4S,5S)-4-Benzyl-5-[(2S,5'S)-5'-benzyl-4-((R)-1-tert-butylcarbamoyl-2-phenyl-ethyl)-2-isobutyl-3,4'-dioxo-2,3,4',5'-tetrahydro-1H,1'H-[2,3']bipyrrolyl-5'-ylmethyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

Chemical Property of (4S,5S)-4-Benzyl-5-[(2S,5'S)-5'-benzyl-4-((R)-1-tert-butylcarbamoyl-2-phenyl-ethyl)-2-isobutyl-3,4'-dioxo-2,3,4',5'-tetrahydro-1H,1'H-[2,3']bipyrrolyl-5'-ylmethyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

Chemical Property:

Purity/Quality:

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Technology Process of (4S,5S)-4-Benzyl-5-[(2S,5'S)-5'-benzyl-4-((R)-1-tert-butylcarbamoyl-2-phenyl-ethyl)-2-isobutyl-3,4'-dioxo-2,3,4',5'-tetrahydro-1H,1'H-[2,3']bipyrrolyl-5'-ylmethyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

There total 22 articles about (4S,5S)-4-Benzyl-5-[(2S,5'S)-5'-benzyl-4-((R)-1-tert-butylcarbamoyl-2-phenyl-ethyl)-2-isobutyl-3,4'-dioxo-2,3,4',5'-tetrahydro-1H,1'H-[2,3']bipyrrolyl-5'-ylmethyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester 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)-4-benzyl-3-(3-phenylpropanoyl)oxazolidin-2-one (136159-65-4,96930-27-7) → (4S,5S)-4-Benzyl-5-[(2S,5'S)-5'-benzyl-4-((R)-1-tert-butylcarbamoyl-2-phenyl-ethyl)-2-isobutyl-3,4'-dioxo-2,3,4',5'-tetrahydro-1H,1'H-[2,3']bipyrrolyl-5'-ylmethyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (173092-09-6)

Guidance literature:

Multi-step reaction with 14 steps

1: 1.) NaHMDS / 1.) THF, -78 deg C, 15 min, 2.) THF, from -78 deg C to 0 deg C, 60 min

2: 1.) n-BuLi / 1.) hexane, THF, 0 deg C, 2.) hexane, THF, 0 deg C, 15 min

3: LAH / tetrahydrofuran / 0.5 h / 0 °C

4: 97 percent / imidazole / dimethylformamide / Ambient temperature

5: 1.) O₃, 2.) Ph₃P / 1.) CH₂Cl₂, -78 deg C, 2.) CH₂Cl₂, RT, overnight

6: CHCl₃; toluene / 4 h

7: KHMDS / 1.) THF, toluene, 20 min, 2.) THF, toluene, 0 deg C, 25 min

8: 1.) NMO, OsO₄, 2.) 2percent aq. NaOH, 3.) Pb(OAc)4

9: CHCl₃; toluene / 4 h

10: 1.) KHMDS / 1.) THF, toluene, RT, 15 min, 2.) THF, toluene, 0 deg C, 15 min

11: 71 percent / Jones reagent / acetonitrile / 4 h / -40 °C

12: 85 percent / Pd(PPh₃)4, dimedone / tetrahydrofuran / 24 h / Ambient temperature

13: Et₃N / tetrahydrofuran / 0.5 h / -10 °C

14: tetrahydrofuran / 0.5 h / -10 °C

With 1H-imidazole; lead(IV) acetate; sodium hydroxide; osmium(VIII) oxide; lithium aluminium tetrahydride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; n-butyllithium; N-methyl-2-indolinone; jones reagent; sodium hexamethyldisilazane; potassium hexamethylsilazane; dimedone; ozone; triethylamine; triphenylphosphine; In tetrahydrofuran; chloroform; N,N-dimethyl-formamide; toluene; acetonitrile;

DOI:10.1021/ja00150a011

Reference yield:

(2R,3S)-3-[N-(tert-butyloxycarbonyl)amino]-1,2-epoxy-4-phenylbutane (98760-08-8) → (4S,5S)-4-Benzyl-5-[(2S,5'S)-5'-benzyl-4-((R)-1-tert-butylcarbamoyl-2-phenyl-ethyl)-2-isobutyl-3,4'-dioxo-2,3,4',5'-tetrahydro-1H,1'H-[2,3']bipyrrolyl-5'-ylmethyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (173092-09-6)

Guidance literature:

Multi-step reaction with 11 steps

1: 1.) KHMDS, 2.) Et₂AlCl / 1.) THF, toluene, -78 deg C, 10 min, 2.) THF, toluene, heptane, -74 deg C, 10 min

2: 91 percent / p-TsOH*H₂O / acetone / 72 h / Ambient temperature

3: 1 N methanolic NaOH / methanol / 72 h / Heating

4: K₂CO₃ / dimethylformamide / 1 h / Ambient temperature

5: 96 percent / Pd(Ph₃P)4, dimedone / tetrahydrofuran / Ambient temperature

6: CHCl₃; toluene / 4 h

7: 1.) KHMDS / 1.) THF, toluene, RT, 15 min, 2.) THF, toluene, 0 deg C, 15 min

8: 71 percent / Jones reagent / acetonitrile / 4 h / -40 °C

9: 85 percent / Pd(PPh₃)4, dimedone / tetrahydrofuran / 24 h / Ambient temperature

10: Et₃N / tetrahydrofuran / 0.5 h / -10 °C

11: tetrahydrofuran / 0.5 h / -10 °C

With sodium hydroxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; jones reagent; diethylaluminium chloride; potassium hexamethylsilazane; potassium carbonate; dimedone; toluene-4-sulfonic acid; triethylamine; In tetrahydrofuran; methanol; chloroform; N,N-dimethyl-formamide; acetone; toluene; acetonitrile;

DOI:10.1021/ja00150a011

Reference yield:

(2R,4R)-4-Benzyl-2-tert-butyl-5-oxo-oxazolidine-3-carboxylic acid allyl ester (147240-29-7) → (4S,5S)-4-Benzyl-5-[(2S,5'S)-5'-benzyl-4-((R)-1-tert-butylcarbamoyl-2-phenyl-ethyl)-2-isobutyl-3,4'-dioxo-2,3,4',5'-tetrahydro-1H,1'H-[2,3']bipyrrolyl-5'-ylmethyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (173092-09-6)

Guidance literature:

Multi-step reaction with 11 steps

1: 1.) KHMDS, 2.) Et₂AlCl / 1.) THF, toluene, -78 deg C, 10 min, 2.) THF, toluene, heptane, -74 deg C, 10 min

2: 91 percent / p-TsOH*H₂O / acetone / 72 h / Ambient temperature

3: 1 N methanolic NaOH / methanol / 72 h / Heating

4: K₂CO₃ / dimethylformamide / 1 h / Ambient temperature

5: 96 percent / Pd(Ph₃P)4, dimedone / tetrahydrofuran / Ambient temperature

6: CHCl₃; toluene / 4 h

7: 1.) KHMDS / 1.) THF, toluene, RT, 15 min, 2.) THF, toluene, 0 deg C, 15 min

8: 71 percent / Jones reagent / acetonitrile / 4 h / -40 °C

9: 85 percent / Pd(PPh₃)4, dimedone / tetrahydrofuran / 24 h / Ambient temperature

10: Et₃N / tetrahydrofuran / 0.5 h / -10 °C

11: tetrahydrofuran / 0.5 h / -10 °C

With sodium hydroxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; jones reagent; diethylaluminium chloride; potassium hexamethylsilazane; potassium carbonate; dimedone; toluene-4-sulfonic acid; triethylamine; In tetrahydrofuran; methanol; chloroform; N,N-dimethyl-formamide; acetone; toluene; acetonitrile;

DOI:10.1021/ja00150a011

upstream raw materials:

tert-butylamine

(S)-4-benzyl-3-(3-phenylpropanoyl)oxazolidin-2-one

(2R,3S)-3-[N-(tert-butyloxycarbonyl)amino]-1,2-epoxy-4-phenylbutane

(2R,4R)-4-Benzyl-2-tert-butyl-5-oxo-oxazolidine-3-carboxylic acid allyl ester

Downstream raw materials:

(R)-2-[(2S,5'S)-5'-((2S,3S)-3-Amino-2-hydroxy-4-phenyl-butyl)-5'-benzyl-2-isobutyl-3,4'-dioxo-2,3,4',5'-tetrahydro-1H,1'H-[2,3']bipyrrolyl-4-yl]-N-tert-butyl-3-phenyl-propionamide

{(1S,2S)-1-Benzyl-3-[(2S,5'S)-5'-benzyl-4-((R)-1-tert-butylcarbamoyl-2-phenyl-ethyl)-2-isobutyl-3,4'-dioxo-2,3,4',5'-tetrahydro-1H,1'H-[2,3']bipyrrolyl-5'-yl]-2-hydroxy-propyl}-carbamic acid (S)-(tetrahydro-furan-3-yl) ester

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