tetrahydrofuran-3-yl {(1R,2S)-1-[(13S,16R)-12,15-dioxo-13-(propan-2-yl)-2,5,8-trioxa-11,14,17-triazabicyclo[17.2.2]tricosa-1(21),19,22-trien-16-yl]-1-hydroxy-3-phenylpropan-2-yl}carbamate

Base Information

• Chemical Name: tetrahydrofuran-3-yl {(1R,2S)-1-[(13S,16R)-12,15-dioxo-13-(propan-2-yl)-2,5,8-trioxa-11,14,17-triazabicyclo[17.2.2]tricosa-1(21),19,22-trien-16-yl]-1-hydroxy-3-phenylpropan-2-yl}carbamate
• CAS No.: 180968-44-9
• Molecular Formula: C₃₄H₄₈N₄O₉
• Molecular Weight: 656.777
• Mol file: 180968-44-9.mol

Synonyms:

Chemical Property of tetrahydrofuran-3-yl {(1R,2S)-1-[(13S,16R)-12,15-dioxo-13-(propan-2-yl)-2,5,8-trioxa-11,14,17-triazabicyclo[17.2.2]tricosa-1(21),19,22-trien-16-yl]-1-hydroxy-3-phenylpropan-2-yl}carbamate

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Boiling Point: 929.7°C at 760 mmHg
• Flash Point: 516.1°C
• Density: 1.26g/cm³

Purity/Quality:

99%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tetrahydrofuran-3-yl {(1R,2S)-1-[(13S,16R)-12,15-dioxo-13-(propan-2-yl)-2,5,8-trioxa-11,14,17-triazabicyclo[17.2.2]tricosa-1(21),19,22-trien-16-yl]-1-hydroxy-3-phenylpropan-2-yl}carbamate

There total 11 articles about tetrahydrofuran-3-yl {(1R,2S)-1-[(13S,16R)-12,15-dioxo-13-(propan-2-yl)-2,5,8-trioxa-11,14,17-triazabicyclo[17.2.2]tricosa-1(21),19,22-trien-16-yl]-1-hydroxy-3-phenylpropan-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:

2-(2-(2-aminoethoxy)ethoxy)ethan-1-ol (6338-55-2) → [(1S,2R)-1-Benzyl-2-hydroxy-2-((13S,16R)-13-isopropyl-12,15-dioxo-2,5,8-trioxa-11,14,17-triaza-bicyclo[17.2.2]tricosa-1(22),19(23),20-trien-16-yl)-ethyl]-carbamic acid (S)-(tetrahydro-furan-3-yl) ester (180968-44-9)

Guidance literature:

Multi-step reaction with 10 steps

1: 1-hydroxybenzotriazole, N-ethyl-N'-(3-(dimethylamino)propyl)carbodiimide hydrochloride / dimethylformamide / 24 h / Ambient temperature

2: pyridine / CH₂Cl₂ / 12 h / 0 - 20 °C

3: K₂CO₃, tetrabutylammonium iodide / dimethylsulfoxide / 4 h / 70 °C

4: hydroxyammonium chloride, aq. AcONa / ethanol / 1.5 h / 60 °C

5: formic acid, H₂ / 10percent Pd/C / methanol / 3 h / 760 Torr

6: ethanol / 24 h / 80 °C

7: 0.4 M aq. LiOH / dioxane / 16 h / Ambient temperature

8: 3,4-dihydro-3-hydroxy-4-oxo-1,2,3-benzotriazine, N-ethyl-N'-(3-(dimethylamino)propyl)carbodiimide hydrochloride / tetrahydrofuran / 120 h / Ambient temperature

9: 18percent aq. HCl / dioxane

10: 1.) pyridine, 2.) pyridine / 1.) toluol, dichloromethane, 0 deg C, 2.) toluol, dichloromethane, RT, 16 h

With pyridine; hydrogenchloride; lithium hydroxide; formic acid; hydroxylamine hydrochloride; hydrogen; sodium acetate; tetra-(n-butyl)ammonium iodide; potassium carbonate; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; 3-hydroxy-3,4-dihydrobenzotriazine-4-one; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; methanol; ethanol; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide;

DOI:10.1021/jm950641i

Reference yield:

(S)-N-(benzyloxycarbonyl)valine (1149-26-4) → [(1S,2R)-1-Benzyl-2-hydroxy-2-((13S,16R)-13-isopropyl-12,15-dioxo-2,5,8-trioxa-11,14,17-triaza-bicyclo[17.2.2]tricosa-1(22),19(23),20-trien-16-yl)-ethyl]-carbamic acid (S)-(tetrahydro-furan-3-yl) ester (180968-44-9)

Guidance literature:

Multi-step reaction with 10 steps

1: 1-hydroxybenzotriazole, N-ethyl-N'-(3-(dimethylamino)propyl)carbodiimide hydrochloride / dimethylformamide / 24 h / Ambient temperature

2: pyridine / CH₂Cl₂ / 12 h / 0 - 20 °C

3: K₂CO₃, tetrabutylammonium iodide / dimethylsulfoxide / 4 h / 70 °C

4: hydroxyammonium chloride, aq. AcONa / ethanol / 1.5 h / 60 °C

5: formic acid, H₂ / 10percent Pd/C / methanol / 3 h / 760 Torr

6: ethanol / 24 h / 80 °C

7: 0.4 M aq. LiOH / dioxane / 16 h / Ambient temperature

8: 3,4-dihydro-3-hydroxy-4-oxo-1,2,3-benzotriazine, N-ethyl-N'-(3-(dimethylamino)propyl)carbodiimide hydrochloride / tetrahydrofuran / 120 h / Ambient temperature

9: 18percent aq. HCl / dioxane

10: 1.) pyridine, 2.) pyridine / 1.) toluol, dichloromethane, 0 deg C, 2.) toluol, dichloromethane, RT, 16 h

With pyridine; hydrogenchloride; lithium hydroxide; formic acid; hydroxylamine hydrochloride; hydrogen; sodium acetate; tetra-(n-butyl)ammonium iodide; potassium carbonate; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; 3-hydroxy-3,4-dihydrobenzotriazine-4-one; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; methanol; ethanol; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide;

DOI:10.1021/jm950641i

Reference yield:

((S)-1-{2-[2-(2-Hydroxy-ethoxy)-ethoxy]-ethylcarbamoyl}-2-methyl-propyl)-carbamic acid benzyl ester → [(1S,2R)-1-Benzyl-2-hydroxy-2-((13S,16R)-13-isopropyl-12,15-dioxo-2,5,8-trioxa-11,14,17-triaza-bicyclo[17.2.2]tricosa-1(22),19(23),20-trien-16-yl)-ethyl]-carbamic acid (S)-(tetrahydro-furan-3-yl) ester (180968-44-9)

Guidance literature:

Multi-step reaction with 9 steps

1: pyridine / CH₂Cl₂ / 12 h / 0 - 20 °C

2: K₂CO₃, tetrabutylammonium iodide / dimethylsulfoxide / 4 h / 70 °C

3: hydroxyammonium chloride, aq. AcONa / ethanol / 1.5 h / 60 °C

4: formic acid, H₂ / 10percent Pd/C / methanol / 3 h / 760 Torr

5: ethanol / 24 h / 80 °C

6: 0.4 M aq. LiOH / dioxane / 16 h / Ambient temperature

7: 3,4-dihydro-3-hydroxy-4-oxo-1,2,3-benzotriazine, N-ethyl-N'-(3-(dimethylamino)propyl)carbodiimide hydrochloride / tetrahydrofuran / 120 h / Ambient temperature

8: 18percent aq. HCl / dioxane

9: 1.) pyridine, 2.) pyridine / 1.) toluol, dichloromethane, 0 deg C, 2.) toluol, dichloromethane, RT, 16 h

With pyridine; hydrogenchloride; lithium hydroxide; formic acid; hydroxylamine hydrochloride; hydrogen; sodium acetate; tetra-(n-butyl)ammonium iodide; potassium carbonate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; 3-hydroxy-3,4-dihydrobenzotriazine-4-one; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; methanol; ethanol; dichloromethane; dimethyl sulfoxide;

DOI:10.1021/jm950641i

upstream raw materials:

phosgene

(S)-3-hydroxytetyrahydrofurane

2-(2-(2-aminoethoxy)ethoxy)ethan-1-ol

(S)-N-(benzyloxycarbonyl)valine

Refernces