(2S)-3,6-Dioxo-1,4-dioxane-2-propanoic acid benzyl ester

Base Information

• Chemical Name: (2S)-3,6-Dioxo-1,4-dioxane-2-propanoic acid benzyl ester
• CAS No.: 872139-38-3
• Molecular Formula: C14H14O6
• Molecular Weight: 278.26
• Mol file: 872139-38-3.mol

Synonyms:(2S)-3,6-Dioxo-1,4-dioxane-2-propanoic acid benzyl ester

Chemical Property of (2S)-3,6-Dioxo-1,4-dioxane-2-propanoic acid benzyl ester

Chemical Property:

• Refractive Index: 1.529
• Boiling Point: 463.8 °C at 760 mmHg
• Flash Point: 208.5 °C
• PSA: 78.90000
• Density: 1.286 g/cm³
• LogP: 0.97860

Purity/Quality:

99% ^*data from raw suppliers

(2S)-3,6-Dioxo-1,4-dioxane-2-propanoic acid benzylester ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (2S)-3,6-Dioxo-1,4-dioxane-2-propanoic acid benzyl ester

There total 5 articles about (2S)-3,6-Dioxo-1,4-dioxane-2-propanoic acid benzyl 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: 54.0%

5-benzyloxycarbonyl-2-(2-bromo-acetyloxy)-pentandioic acid (872139-37-2) → (3S)-[(benzyloxycarbonyl)ethyl]-1,4-dioxan-2,5-dione (872139-38-3)

Guidance literature:

With tetra-(n-butyl)ammonium iodide; N-ethyl-N,N-diisopropylamine; In 4-methyl-2-pentanone; at 20 - 60 ℃; Inert atmosphere;

DOI:10.1021/bm100433c

Reference yield:

L-glutamic acid (56-86-0,21675-62-7,23009-64-5,25104-13-6,84960-48-5,25513-46-6) → (3S)-[(benzyloxycarbonyl)ethyl]-1,4-dioxan-2,5-dione (872139-38-3)

Guidance literature:

Multi-step reaction with 4 steps

1.1: methanesulfonic acid / toluene / 5 h / 30 - 45 °C / Inert atmosphere

2.1: acetic acid; sodium nitrite / water / 4 h / 30 °C / Inert atmosphere

2.2: 0.5 h / Inert atmosphere; Cooling

3.1: triethylamine / dichloromethane / 4 h / Inert atmosphere

4.1: tetra-(n-butyl)ammonium iodide; N-ethyl-N,N-diisopropylamine / 4-methyl-2-pentanone / 20 - 60 °C / Inert atmosphere

With methanesulfonic acid; tetra-(n-butyl)ammonium iodide; acetic acid; triethylamine; N-ethyl-N,N-diisopropylamine; sodium nitrite; In dichloromethane; water; 4-methyl-2-pentanone; toluene;

DOI:10.1021/bm100433c

Reference yield:

L-glutamic acid γ-benzyl ester (1676-73-9,25014-27-1) → (3S)-[(benzyloxycarbonyl)ethyl]-1,4-dioxan-2,5-dione (872139-38-3)

Guidance literature:

Multi-step reaction with 3 steps

1.1: acetic acid; sodium nitrite / water / 4 h / 30 °C / Inert atmosphere

1.2: 0.5 h / Inert atmosphere; Cooling

2.1: triethylamine / dichloromethane / 4 h / Inert atmosphere

3.1: tetra-(n-butyl)ammonium iodide; N-ethyl-N,N-diisopropylamine / 4-methyl-2-pentanone / 20 - 60 °C / Inert atmosphere

With tetra-(n-butyl)ammonium iodide; acetic acid; triethylamine; N-ethyl-N,N-diisopropylamine; sodium nitrite; In dichloromethane; water; 4-methyl-2-pentanone;

DOI:10.1021/bm100433c

upstream raw materials:

5-benzyloxycarbonyl-2-(2-bromo-acetyloxy)-pentandioic acid

L-glutamic acid

L-glutamic acid γ-benzyl ester

benzyl alcohol

Refernces