1,2,5-Pentanetricarboxylic acid, 1-(acetyloxy)-2-(phenylthio)-, 1,2-diethyl 5-methyl ester, (1S)-

Base Information

• Chemical Name: 1,2,5-Pentanetricarboxylic acid, 1-(acetyloxy)-2-(phenylthio)-, 1,2-diethyl 5-methyl ester, (1S)-
• CAS No.: 928169-73-7
• Molecular Formula: C₂₁H₂₈O₈S
• Molecular Weight: 440.515
• Mol file: 928169-73-7.mol

Synonyms:

Chemical Property of 1,2,5-Pentanetricarboxylic acid, 1-(acetyloxy)-2-(phenylthio)-, 1,2-diethyl 5-methyl ester, (1S)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1,2,5-Pentanetricarboxylic acid, 1-(acetyloxy)-2-(phenylthio)-, 1,2-diethyl 5-methyl ester, (1S)-

There total 5 articles about 1,2,5-Pentanetricarboxylic acid, 1-(acetyloxy)-2-(phenylthio)-, 1,2-diethyl 5-methyl ester, (1S)- 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:

diethyl (2R,3S)-3-{4-(t-butyldimethylsilyloxy)butyl}malate (928169-64-6) → diethyl (2R)-2-O-acetyl-3-(3-methoxycarbonyl-propyl)-3-(phenylthio)malate (928169-73-7)

Guidance literature:

Multi-step reaction with 5 steps

1.1: lithium diisopropylamide / tetrahydrofuran; hexane / -20 °C

1.2: tetrahydrofuran; hexane / 0 °C

2.1: 4-(dimethylamino)pyridine; triethylamine / CH₂Cl₂ / 20 °C

3.1: 96 percent / pyridinium p-toluenesulfonate / ethanol / 10 h / 20 °C

4.1: pyridinium dichromate / dimethylformamide / 18 h / 20 °C

5.1: 420 mg / methanol; diethyl ether / 0.5 h / 20 °C

With dmap; dipyridinium dichromate; pyridinium p-toluenesulfonate; triethylamine; lithium diisopropyl amide; In tetrahydrofuran; methanol; diethyl ether; ethanol; hexane; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/j.bmc.2006.11.008

Reference yield:

C17H33O6SiSC6H5CH2 → diethyl (2R)-2-O-acetyl-3-(3-methoxycarbonyl-propyl)-3-(phenylthio)malate (928169-73-7)

Guidance literature:

Multi-step reaction with 4 steps

1: 4-(dimethylamino)pyridine; triethylamine / CH₂Cl₂ / 20 °C

2: 96 percent / pyridinium p-toluenesulfonate / ethanol / 10 h / 20 °C

3: pyridinium dichromate / dimethylformamide / 18 h / 20 °C

4: 420 mg / methanol; diethyl ether / 0.5 h / 20 °C

With dmap; dipyridinium dichromate; pyridinium p-toluenesulfonate; triethylamine; In methanol; diethyl ether; ethanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/j.bmc.2006.11.008

Reference yield:

diethyl (2R)-2-O-acetyl-3-{4-(t-butyldimethylsilyloxy)butyl}-3-(phenylthio)malate (928169-72-6) → diethyl (2R)-2-O-acetyl-3-(3-methoxycarbonyl-propyl)-3-(phenylthio)malate (928169-73-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 96 percent / pyridinium p-toluenesulfonate / ethanol / 10 h / 20 °C

2: pyridinium dichromate / dimethylformamide / 18 h / 20 °C

3: 420 mg / methanol; diethyl ether / 0.5 h / 20 °C

With dipyridinium dichromate; pyridinium p-toluenesulfonate; In methanol; diethyl ether; ethanol; N,N-dimethyl-formamide;

DOI:10.1016/j.bmc.2006.11.008

upstream raw materials:

diethyl (2R,3S)-3-{4-(t-butyldimethylsilyloxy)butyl}malate

diethyl (2R)-2-O-acetyl-3-{4-(t-butyldimethylsilyloxy)butyl}-3-(phenylthio)malate

C₁₁H₁₉O₆SC₆H₅(CH₂CO)CH₂

diethyl (R)-malate

Refernces