4-allyl 1-[(2S)-2-(benzylamino)-3-methoxy-3-oxopropyl] N-(tert-butoxycarbonyl)-D-aspartate

Base Information

• Chemical Name: 4-allyl 1-[(2S)-2-(benzylamino)-3-methoxy-3-oxopropyl] N-(tert-butoxycarbonyl)-D-aspartate
• CAS No.: 1389331-94-5
• Molecular Formula: C₂₃H₃₂N₂O₈
• Molecular Weight: 464.516
• Mol file: 1389331-94-5.mol

Synonyms:4-allyl 1-[(2S)-2-(benzylamino)-3-methoxy-3-oxopropyl] N-(tert-butoxycarbonyl)-D-aspartate

Chemical Property of 4-allyl 1-[(2S)-2-(benzylamino)-3-methoxy-3-oxopropyl] N-(tert-butoxycarbonyl)-D-aspartate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-allyl 1-[(2S)-2-(benzylamino)-3-methoxy-3-oxopropyl] N-(tert-butoxycarbonyl)-D-aspartate

There total 1 articles about 4-allyl 1-[(2S)-2-(benzylamino)-3-methoxy-3-oxopropyl] N-(tert-butoxycarbonyl)-D-aspartate 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: 94.0%

(S)-N-benzylserine methyl ester (123639-56-5) + (R)-4-(allyloxy)-2-((tert-butoxycarbonyl)amino)-4-oxobutanoic acid (207120-58-9) → 4-allyl 1-[(2S)-2-(benzylamino)-3-methoxy-3-oxopropyl] N-(tert-butoxycarbonyl)-D-aspartate (1389331-94-5)

Guidance literature:

With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 0 - 20 ℃; for 6h; Inert atmosphere;

DOI:10.1002/chem.201200457

Reference yield:

4-allyl 1-[(2S)-2-(benzylamino)-3-methoxy-3-oxopropyl] N-(tert-butoxycarbonyl)-D-aspartate (1389331-94-5) → C40H55N9O11S (1389332-25-5)

Guidance literature:

Multi-step reaction with 10 steps

1.1: dichloromethane / 2 h / 20 °C / Inert atmosphere

2.1: N-ethyl-N,N-diisopropylamine / isopropyl alcohol / 18 h / 20 °C / Inert atmosphere

3.1: hydrogen azide; di-isopropyl azodicarboxylate; triphenylphosphine / dichloromethane; toluene / 3.5 h / -20 °C / Inert atmosphere

4.1: trimethylphosphane / tetrahydrofuran / 5 h / -20 - 20 °C / Inert atmosphere

5.1: pyrrolidine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; triphenylphosphine / dichloromethane / 1 h / 0 °C / Inert atmosphere

6.1: 1-hydroxy-7-aza-benzotriazole; N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide / 0.5 h / 0 °C / Inert atmosphere

6.2: 0 - 20 °C / Inert atmosphere

7.1: dichloromethane / 2 h / 20 °C / Inert atmosphere

8.1: 1-hydroxy-7-aza-benzotriazole; N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide / 0.5 h / 0 °C / Inert atmosphere

8.2: 0 - 20 °C / Inert atmosphere

9.1: palladium 10% on activated carbon; hydrogen / tetrahydrofuran; water / 20 °C / 750.08 Torr / Inert atmosphere

10.1: diphenyl phosphoryl azide; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 53 h / 0 - 20 °C / Inert atmosphere

With pyrrolidine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; hydrogen azide; 1-hydroxy-7-aza-benzotriazole; di-isopropyl azodicarboxylate; diphenyl phosphoryl azide; palladium 10% on activated carbon; hydrogen; N-ethyl-N,N-diisopropylamine; triphenylphosphine; HATU; trimethylphosphane; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; isopropyl alcohol; toluene; 3.1: Mitsunobu reaction;

DOI:10.1002/chem.201200457

Reference yield:

4-allyl 1-[(2S)-2-(benzylamino)-3-methoxy-3-oxopropyl] N-(tert-butoxycarbonyl)-D-aspartate (1389331-94-5) → C2HF3O2*C26H35N9O8 (1389332-05-1)

Guidance literature:

Multi-step reaction with 11 steps

1.1: dichloromethane / 2 h / 20 °C / Inert atmosphere

2.1: N-ethyl-N,N-diisopropylamine / isopropyl alcohol / 18 h / 20 °C / Inert atmosphere

3.1: hydrogen azide; di-isopropyl azodicarboxylate; triphenylphosphine / dichloromethane; toluene / 3.5 h / -20 °C / Inert atmosphere

4.1: trimethylphosphane / tetrahydrofuran / 5 h / -20 - 20 °C / Inert atmosphere

5.1: pyrrolidine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; triphenylphosphine / dichloromethane / 1 h / 0 °C / Inert atmosphere

6.1: 1-hydroxy-7-aza-benzotriazole; N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide / 0.5 h / 0 °C / Inert atmosphere

6.2: 0 - 20 °C / Inert atmosphere

7.1: dichloromethane / 2 h / 20 °C / Inert atmosphere

8.1: 1-hydroxy-7-aza-benzotriazole; N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide / 0.5 h / 0 °C / Inert atmosphere

8.2: 0 - 20 °C / Inert atmosphere

9.1: palladium 10% on activated carbon; hydrogen / tetrahydrofuran; water / 20 °C / 750.08 Torr / Inert atmosphere

10.1: diphenyl phosphoryl azide; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 53 h / 0 - 20 °C / Inert atmosphere

11.1: methyl-phenyl-thioether; ethane-1,2-dithiol; methoxybenzene / Inert atmosphere

With pyrrolidine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; hydrogen azide; 1-hydroxy-7-aza-benzotriazole; methyl-phenyl-thioether; di-isopropyl azodicarboxylate; diphenyl phosphoryl azide; palladium 10% on activated carbon; hydrogen; ethane-1,2-dithiol; methoxybenzene; N-ethyl-N,N-diisopropylamine; triphenylphosphine; HATU; trimethylphosphane; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; isopropyl alcohol; toluene; 3.1: Mitsunobu reaction;

DOI:10.1002/chem.201200457

upstream raw materials:

(S)-N-benzylserine methyl ester

(R)-4-(allyloxy)-2-((tert-butoxycarbonyl)amino)-4-oxobutanoic acid

Downstream raw materials:

C₄₄H₅₈N₈O₁₁S

C₅₅H₆₉N₉O₁₄S

C₄₀H₅₇N₉O₁₂S

C₄₀H₅₅N₉O₁₁S