[(3S)-oxolan-3-yl] N-[(2S,3S)-4-[(2S)-2-benzyl-4-[(2S)-4-[(2R)-1-(tert-butylamino)-1-oxo-3-phenylpropan-2-yl]-2-(2-methylpropyl)-3-oxo-1H-pyrrol-2-yl]-3-oxo-1H-pyrrol-2-yl]-3-hydroxy-1-phenylbutan-2-yl]carbamate

Base Information

• Chemical Name: [(3S)-oxolan-3-yl] N-[(2S,3S)-4-[(2S)-2-benzyl-4-[(2S)-4-[(2R)-1-(tert-butylamino)-1-oxo-3-phenylpropan-2-yl]-2-(2-methylpropyl)-3-oxo-1H-pyrrol-2-yl]-3-oxo-1H-pyrrol-2-yl]-3-hydroxy-1-phenylbutan-2-yl]carbamate
• CAS No.: 173091-97-9
• Molecular Formula: C₄₇H₅₈N₄O₇
• Molecular Weight: 791
• DSSTox Substance ID: DTXSID20938295
• Wikidata: Q82914581
• Mol file: 173091-97-9.mol

Synonyms:173091-97-9;[(3S)-oxolan-3-yl] N-[(2S,3S)-4-[(2S)-2-benzyl-4-[(2S)-4-[(2R)-1-(tert-butylamino)-1-oxo-3-phenylpropan-2-yl]-2-(2-methylpropyl)-3-oxo-1H-pyrrol-2-yl]-3-oxo-1H-pyrrol-2-yl]-3-hydroxy-1-phenylbutan-2-yl]carbamate;Carbamic acid, ((1S,2S)-3-((2S,5'S)-4-((1R)-2-((1,1-dimethylethyl)amino)-2-oxo-1-(phenylmethyl)ethyl)-2,3,4',5'-tetrahydro-2-(2-methylpropyl)-3,4'-dioxo-5'-(phenylmethyl)(2,3'-bi-1H-pyrrol)-5'-yl)-2-hydroxy-1-(phenylmethyl)propyl)-, (3S)-tetrahydro-3-furanyl ester;Carbamic acid, [(1S,2S)-3-[(2S,5'S)-4-[(1R)-2-[(1,1-dimethylethyl)amino]-2-oxo-1-(phenylmethyl)ethyl]-2,3,4',5'-tetrahydro-2-(2-methylpropyl)-3,4'-dioxo-5'-(phenylmethyl)[2,3'-bi-1H-pyrrol]-5'-yl]-2-hydroxy-1-(phenylmethyl)propyl]-, (3S)-tetrahydro-3-furanyl ester;DTXSID20938295;CQYRFIYZAKSRRG-UPMBQMLSSA-N;[(3S)-tetrahydrofuran-3-yl] N-[(1S,2S)-1-benzyl-3-[(2S)-2-benzyl-4-[(2S)-4-[(1R)-1-benzyl-2-(tert-butylamino)-2-oxo-ethyl]-2-isobutyl-3-oxo-1H-pyrrol-2-yl]-3-oxo-1H-pyrrol-2-yl]-2-hydroxy-propyl]carbamate;2-{5'-Benzyl-5'-[2-hydroxy-3-({hydroxy[(oxolan-3-yl)oxy]methylidene}amino)-4-phenylbutyl]-2-(2-methylpropyl)-3,4'-dioxo-2,3,4',5'-tetrahydro-1H,1'H-[2,3'-bipyrrol]-4-yl}-N-tert-butyl-3-phenylpropanimidic acid

Chemical Property of [(3S)-oxolan-3-yl] N-[(2S,3S)-4-[(2S)-2-benzyl-4-[(2S)-4-[(2R)-1-(tert-butylamino)-1-oxo-3-phenylpropan-2-yl]-2-(2-methylpropyl)-3-oxo-1H-pyrrol-2-yl]-3-oxo-1H-pyrrol-2-yl]-3-hydroxy-1-phenylbutan-2-yl]carbamate

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Boiling Point: 964.7°Cat760mmHg
• Flash Point: 537.2°C
• PSA: 162.07000
• Density: 1.24g/cm³
• LogP: 7.21850
• XLogP3: 7
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 18
• Exact Mass: 790.43055020
• Heavy Atom Count: 58
• Complexity: 1500

Purity/Quality:

99%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)CC1(C(=O)C(=CN1)C(CC2=CC=CC=C2)C(=O)NC(C)(C)C)C3=CNC(C3=O)(CC4=CC=CC=C4)CC(C(CC5=CC=CC=C5)NC(=O)OC6CCOC6)O
• Isomeric SMILES: CC(C)C[C@@]1(C(=O)C(=CN1)[C@@H](CC2=CC=CC=C2)C(=O)NC(C)(C)C)C3=CN[C@@](C3=O)(CC4=CC=CC=C4)C[C@@H]([C@H](CC5=CC=CC=C5)NC(=O)O[C@H]6CCOC6)O

Technology Process of [(3S)-oxolan-3-yl] N-[(2S,3S)-4-[(2S)-2-benzyl-4-[(2S)-4-[(2R)-1-(tert-butylamino)-1-oxo-3-phenylpropan-2-yl]-2-(2-methylpropyl)-3-oxo-1H-pyrrol-2-yl]-3-oxo-1H-pyrrol-2-yl]-3-hydroxy-1-phenylbutan-2-yl]carbamate

There total 24 articles about [(3S)-oxolan-3-yl] N-[(2S,3S)-4-[(2S)-2-benzyl-4-[(2S)-4-[(2R)-1-(tert-butylamino)-1-oxo-3-phenylpropan-2-yl]-2-(2-methylpropyl)-3-oxo-1H-pyrrol-2-yl]-3-oxo-1H-pyrrol-2-yl]-3-hydroxy-1-phenylbutan-2-yl]carbamate 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: 66.0%

1-({[(3S)-tetrahydro-3-furanyloxy]carbonyl}oxy)-2,5-pyrrolidinedione (138499-08-8) + (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 (173091-95-7) → {(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 (173091-97-9)

Guidance literature:

With triethylamine; In dichloromethane; for 2.5h; Ambient temperature;

DOI:10.1021/ja00150a011

Reference yield:

(S)-4-benzyl-3-(3-phenylpropanoyl)oxazolidin-2-one (136159-65-4,96930-27-7) → {(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 (173091-97-9)

Guidance literature:

Multi-step reaction with 16 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

15: 78 percent / HCl / methanol / 18 h / Ambient temperature

16: 66 percent / Et₃N / CH₂Cl₂ / 2.5 h / Ambient temperature

With 1H-imidazole; lead(IV) acetate; hydrogenchloride; 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; methanol; dichloromethane; 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) → {(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 (173091-97-9)

Guidance literature:

Multi-step reaction with 13 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

12: 78 percent / HCl / methanol / 18 h / Ambient temperature

13: 66 percent / Et₃N / CH₂Cl₂ / 2.5 h / Ambient temperature

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

DOI:10.1021/ja00150a011

upstream raw materials:

1-({[(3S)-tetrahydro-3-furanyloxy]carbonyl}oxy)-2,5-pyrrolidinedione

(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

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

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

Refernces