1,2-Pyrrolidinedicarboxylic acid, 2-[(1S)-1-(acetyloxy)-2-methylpropyl]-3-hydroxy-4-methyl-5-oxo-, 1-(1,1-dimethylethyl) 2-methyl ester, (2S,3S,4R)-

Base Information

• Chemical Name: 1,2-Pyrrolidinedicarboxylic acid, 2-[(1S)-1-(acetyloxy)-2-methylpropyl]-3-hydroxy-4-methyl-5-oxo-, 1-(1,1-dimethylethyl) 2-methyl ester, (2S,3S,4R)-
• CAS No.: 928209-78-3
• Molecular Formula: C18H29NO8
• Molecular Weight: 387.43
• Mol file: 928209-78-3.mol

Synonyms:

Chemical Property of 1,2-Pyrrolidinedicarboxylic acid, 2-[(1S)-1-(acetyloxy)-2-methylpropyl]-3-hydroxy-4-methyl-5-oxo-, 1-(1,1-dimethylethyl) 2-methyl ester, (2S,3S,4R)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 1,2-Pyrrolidinedicarboxylic acid, 2-[(1S)-1-(acetyloxy)-2-methylpropyl]-3-hydroxy-4-methyl-5-oxo-, 1-(1,1-dimethylethyl) 2-methyl ester, (2S,3S,4R)-

There total 1 articles about 1,2-Pyrrolidinedicarboxylic acid, 2-[(1S)-1-(acetyloxy)-2-methylpropyl]-3-hydroxy-4-methyl-5-oxo-, 1-(1,1-dimethylethyl) 2-methyl ester, (2S,3S,4R)- 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:

(S)-Pyroglutaminol (17342-08-4) → 2-(1-acetoxy-2-methyl-propyl)-3-hydroxy-4-methyl-5-oxo-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester (928209-78-3)

Guidance literature:

Multi-step reaction with 16 steps

1.1: toluene-4-sulfonic acid / toluene / 44 h / Reflux; Inert atmosphere

2.1: benzophenone / tert-butyl alcohol / 20 h / 20 °C / Photolysis; Inert atmosphere

3.1: potassium carbonate / methanol / 3 h / 0 - 20 °C / Inert atmosphere

4.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / 0 - 20 °C / Inert atmosphere

4.2: 12 h / -40 - 0 °C / Inert atmosphere

5.1: ruthenium (IV) oxide monohydrate; sodium periodate / acetonitrile; tetrachloromethane; water / 0.5 h / 0 °C / Darkness

6.1: benzene / 18 h / 20 °C / Photolysis; Inert atmosphere

7.1: sodium carbonate; lead(IV) tetraacetate / methanol; benzene / 0.25 h / 0 °C / Inert atmosphere

8.1: dimethyltitanocene / toluene / 12 h / 20 - 85 °C / Inert atmosphere

9.1: trifluoroacetic acid / tetrahydrofuran; water / 3 h / 20 - 60 °C

10.1: dmap / pyridine / 5 h / 20 °C / Inert atmosphere

11.1: dmap; triethylamine / dichloromethane / 20 h / 20 °C / Inert atmosphere

12.1: hydrogen; palladium 10% on activated carbon / ethyl acetate / 13 h / 20 °C

13.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere

13.2: 0.5 h / Inert atmosphere

14.1: sodium hydrogencarbonate; dihydrogen peroxide / tetrahydrofuran; ethyl acetate; water / 1 h / 0 - 20 °C

15.1: diethylzinc / tetrahydrofuran; hexane / 0.5 h / -78 - 0 °C / Inert atmosphere

15.2: -78 - 20 °C / Inert atmosphere

16.1: potassium hydrogenfluoride; 3-chloro-benzenecarboperoxoic acid / N,N-dimethyl-formamide / 18 h / 0 - 20 °C / Inert atmosphere

With dmap; sodium periodate; n-butyllithium; benzophenone; potassium hydrogenfluoride; dimethyltitanocene; ruthenium (IV) oxide monohydrate; palladium 10% on activated carbon; hydrogen; dihydrogen peroxide; diethylzinc; lead(IV) tetraacetate; sodium hydrogencarbonate; sodium carbonate; potassium carbonate; toluene-4-sulfonic acid; triethylamine; 3-chloro-benzenecarboperoxoic acid; trifluoroacetic acid; lithium hexamethyldisilazane; In tetrahydrofuran; pyridine; methanol; tetrachloromethane; hexane; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; toluene; acetonitrile; tert-butyl alcohol; benzene;

DOI:10.1021/ol503291s

Reference yield:

2-(1-acetoxy-2-methyl-propyl)-3-hydroxy-4-methyl-5-oxo-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester (928209-78-3) → Lactacystin (133343-34-7)

Guidance literature:

Multi-step reaction with 4 steps

1: trifluoroacetic acid / dichloromethane / 4 - 20 °C

2: water; sodium hydroxide / 64 h / 4 °C

3: bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride; triethylamine / dichloromethane / 2 h

4: triethylamine / dichloromethane / 20 - 23 °C

With water; bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride; triethylamine; trifluoroacetic acid; sodium hydroxide; In dichloromethane;

DOI:10.1021/jo201453x

Reference yield:

2-(1-acetoxy-2-methyl-propyl)-3-hydroxy-4-methyl-5-oxo-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester (928209-78-3) → omuralide (154226-60-5,186833-31-8,155975-72-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 75 percent / trifluoroacetic acid / CH₂Cl₂ / 3 h / 20 °C

2: aq. NaOH / 72 h / 20 °C

3: 16 mg / triethylamine; bis(2-oxo-3-oxazolidinyl)phosphonic chloride / CH₂Cl₂ / 3 h / 20 °C

With sodium hydroxide; bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride; triethylamine; trifluoroacetic acid; In dichloromethane;

DOI:10.1002/ejoc.200600835

upstream raw materials:

(S)-Pyroglutaminol

Downstream raw materials:

omuralide

(3R,4S,5R,1'S)-4-hydroxy-5-(1'-hydroxy-2'-methylpropyl)-3-methylpyrrolidin-2-one-5-carboxylic acid

Lactacystin