[(4R,5S)-2-Hydroxy-2-oxo-4-((E)-pentadec-1-enyl)-2λ⁵-[1,3,2]dioxaphosphinan-5-yl]-carbamic acid 1-(2-nitro-phenyl)-ethyl ester

Base Information

• Chemical Name: [(4R,5S)-2-Hydroxy-2-oxo-4-((E)-pentadec-1-enyl)-2λ⁵-[1,3,2]dioxaphosphinan-5-yl]-carbamic acid 1-(2-nitro-phenyl)-ethyl ester
• CAS No.: 219646-80-7
• Molecular Formula: C₂₇H₄₃N₂O₈P
• Molecular Weight: 554.621
• Mol file: 219646-80-7.mol

Synonyms:

Chemical Property of [(4R,5S)-2-Hydroxy-2-oxo-4-((E)-pentadec-1-enyl)-2λ⁵-[1,3,2]dioxaphosphinan-5-yl]-carbamic acid 1-(2-nitro-phenyl)-ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [(4R,5S)-2-Hydroxy-2-oxo-4-((E)-pentadec-1-enyl)-2λ⁵-[1,3,2]dioxaphosphinan-5-yl]-carbamic acid 1-(2-nitro-phenyl)-ethyl ester

There total 6 articles about [(4R,5S)-2-Hydroxy-2-oxo-4-((E)-pentadec-1-enyl)-2λ⁵-[1,3,2]dioxaphosphinan-5-yl]-carbamic acid 1-(2-nitro-phenyl)-ethyl 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: 83.0%

[(4R,5S)-2-(2-Cyano-ethoxy)-2-oxo-4-((E)-pentadec-1-enyl)-2λ5-[1,3,2]dioxaphosphinan-5-yl]-carbamic acid 1-(2-nitro-phenyl)-ethyl ester (219646-77-2) → [(4R,5S)-2-Hydroxy-2-oxo-4-((E)-pentadec-1-enyl)-2λ5-[1,3,2]dioxaphosphinan-5-yl]-carbamic acid 1-(2-nitro-phenyl)-ethyl ester (219646-80-7)

Guidance literature:

With Dowex 50 (H⁺); diethylamine; 1.) EtOH, 40 deg C, 36 h; 2.) MeOH;

DOI:10.1016/S0040-4039(98)02071-1

Reference yield:

1-(2-nitrophenyl)ethan-1-ol (80379-10-8,108530-03-6,142631-59-2,3205-25-2) → [(4R,5S)-2-Hydroxy-2-oxo-4-((E)-pentadec-1-enyl)-2λ5-[1,3,2]dioxaphosphinan-5-yl]-carbamic acid 1-(2-nitro-phenyl)-ethyl ester (219646-80-7)

Guidance literature:

Multi-step reaction with 6 steps

1: Et₃N / CH₂Cl₂ / 1 h / 0 - 20 °C

2: 85 percent / NaHCO₃ / dioxane; H₂O

3: i-Pr₂NEt / CH₂Cl₂

4: tetrazole

5: t-BuOOH

6: 83 percent / 1.) Et₂NH; 2.) Dowex 50 (H⁺) / 1.) EtOH, 40 deg C, 36 h; 2.) MeOH

With 1H-tetrazole; tert.-butylhydroperoxide; Dowex 50 (H⁺); sodium hydrogencarbonate; diethylamine; triethylamine; N-ethyl-N,N-diisopropylamine; In 1,4-dioxane; dichloromethane; water;

DOI:10.1016/S0040-4039(98)02071-1

Reference yield:

2-(2-nitrophenyl)propyl carbonochloridate (154187-40-3) → [(4R,5S)-2-Hydroxy-2-oxo-4-((E)-pentadec-1-enyl)-2λ5-[1,3,2]dioxaphosphinan-5-yl]-carbamic acid 1-(2-nitro-phenyl)-ethyl ester (219646-80-7)

Guidance literature:

Multi-step reaction with 5 steps

1: 85 percent / NaHCO₃ / dioxane; H₂O

2: i-Pr₂NEt / CH₂Cl₂

3: tetrazole

4: t-BuOOH

5: 83 percent / 1.) Et₂NH; 2.) Dowex 50 (H⁺) / 1.) EtOH, 40 deg C, 36 h; 2.) MeOH

With 1H-tetrazole; tert.-butylhydroperoxide; Dowex 50 (H⁺); sodium hydrogencarbonate; diethylamine; N-ethyl-N,N-diisopropylamine; In 1,4-dioxane; dichloromethane; water;

DOI:10.1016/S0040-4039(98)02071-1

upstream raw materials:

[(4R,5S)-2-(2-Cyano-ethoxy)-2-oxo-4-((E)-pentadec-1-enyl)-2λ⁵-[1,3,2]dioxaphosphinan-5-yl]-carbamic acid 1-(2-nitro-phenyl)-ethyl ester

1-(2-nitrophenyl)ethan-1-ol

2-(2-nitrophenyl)propyl carbonochloridate

((E)-(1S,2R)-2-Hydroxy-1-hydroxymethyl-heptadec-3-enyl)-carbamic acid 1-(2-nitro-phenyl)-ethyl ester