(2S,3R,4R)-4-Acetyl-3-<(methoxycarbonyl)methyl>-2-(methoxymethoxymethyl)-1-(toluene-4-sulfonyl)pyrrolidine

Base Information

• Chemical Name: (2S,3R,4R)-4-Acetyl-3-<(methoxycarbonyl)methyl>-2-(methoxymethoxymethyl)-1-(toluene-4-sulfonyl)pyrrolidine
• CAS No.: 150674-66-1
• Molecular Formula: C₁₉H₂₇NO₇S
• Molecular Weight: 413.492
• Mol file: 150674-66-1.mol

Synonyms:(2S,3R,4R)-4-Acetyl-3-<(methoxycarbonyl)methyl>-2-(methoxymethoxymethyl)-1-(toluene-4-sulfonyl)pyrrolidine

Chemical Property of (2S,3R,4R)-4-Acetyl-3-<(methoxycarbonyl)methyl>-2-(methoxymethoxymethyl)-1-(toluene-4-sulfonyl)pyrrolidine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3R,4R)-4-Acetyl-3-<(methoxycarbonyl)methyl>-2-(methoxymethoxymethyl)-1-(toluene-4-sulfonyl)pyrrolidine

There total 14 articles about (2S,3R,4R)-4-Acetyl-3-<(methoxycarbonyl)methyl>-2-(methoxymethoxymethyl)-1-(toluene-4-sulfonyl)pyrrolidine 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:

(3S,3aS)-3-Hydroxymethyl-6-methyl-2,3,3a,4-tetrahydro-1H-cyclopenta[c]pyrrol-5-one (1026379-71-4) → (2S,3R,4R)-4-Acetyl-3-<(methoxycarbonyl)methyl>-2-(methoxymethoxymethyl)-1-(toluene-4-sulfonyl)pyrrolidine (150674-66-1)

Guidance literature:

Multi-step reaction with 6 steps

1: Ambient temperature

2: 98 percent / H₂ / 10percent Pd/C / ethyl acetate / 1 h / 760 Torr

3: diisopropylethylamine / CH₂Cl₂ / 3 h / Ambient temperature

4: 95 percent / Fe(O), Et₃N, HMPA / diethyl ether; tetrahydrofuran / 1.) r.t., 10 min, 2.) r.t., 2 h

5: 1.) O₃, 2.) Me₂S / 1.) CH₂Cl₂, -78 deg C

With N,N,N,N,N,N-hexamethylphosphoric triamide; iron(II) oxide; dimethylsulfide; hydrogen; ozone; triethylamine; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; In tetrahydrofuran; diethyl ether; dichloromethane; ethyl acetate;

DOI:10.1021/jo00102a021

Reference yield:

(S)-3-(but-2-ynyl)-4-vinyloxazolidin-2-one (158839-32-8) → (2S,3R,4R)-4-Acetyl-3-<(methoxycarbonyl)methyl>-2-(methoxymethoxymethyl)-1-(toluene-4-sulfonyl)pyrrolidine (150674-66-1)

Guidance literature:

Multi-step reaction with 8 steps

1: 1.) Co₂(CO)8, 2.) Me₃NO / 1.) CH₂CL₂, r.t., 1 h, 2.) r.t., 2 h

2: 4 N aq. HCl / 6 h / Heating

3: Ambient temperature

4: 98 percent / H₂ / 10percent Pd/C / ethyl acetate / 1 h / 760 Torr

5: diisopropylethylamine / CH₂Cl₂ / 3 h / Ambient temperature

6: 95 percent / Fe(O), Et₃N, HMPA / diethyl ether; tetrahydrofuran / 1.) r.t., 10 min, 2.) r.t., 2 h

7: 1.) O₃, 2.) Me₂S / 1.) CH₂Cl₂, -78 deg C

With hydrogenchloride; N,N,N,N,N,N-hexamethylphosphoric triamide; iron(II) oxide; dicobalt octacarbonyl; dimethylsulfide; trimethylamine-N-oxide; hydrogen; ozone; triethylamine; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; In tetrahydrofuran; diethyl ether; dichloromethane; ethyl acetate;

DOI:10.1021/jo00102a021

Reference yield:

(3aS,3bS)-6-Methyl-3a,3b,4,7-tetrahydro-3H-2-oxa-7a-azacyclopentapentalene-1,5-dione (158839-31-7) → (2S,3R,4R)-4-Acetyl-3-<(methoxycarbonyl)methyl>-2-(methoxymethoxymethyl)-1-(toluene-4-sulfonyl)pyrrolidine (150674-66-1)

Guidance literature:

Multi-step reaction with 7 steps

1: 4 N aq. HCl / 6 h / Heating

2: Ambient temperature

3: 98 percent / H₂ / 10percent Pd/C / ethyl acetate / 1 h / 760 Torr

4: diisopropylethylamine / CH₂Cl₂ / 3 h / Ambient temperature

5: 95 percent / Fe(O), Et₃N, HMPA / diethyl ether; tetrahydrofuran / 1.) r.t., 10 min, 2.) r.t., 2 h

6: 1.) O₃, 2.) Me₂S / 1.) CH₂Cl₂, -78 deg C

With hydrogenchloride; N,N,N,N,N,N-hexamethylphosphoric triamide; iron(II) oxide; dimethylsulfide; hydrogen; ozone; triethylamine; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; In tetrahydrofuran; diethyl ether; dichloromethane; ethyl acetate;

DOI:10.1021/jo00102a021

upstream raw materials:

methyl [2S-(2α,3β,4β)]-[2-(methoxymethoxy)methyl-4-(1-methylethenyl)-1-(4-methylphenyl)sulfonyl]-3-pyrrolidineacetate

p-toluenesulfonyl chloride

(3S,3aS,6aS)-5-<(Trimethylsilyl)oxy>-3-(methoxymethoxymethyl)-6-methyl-2-(toluene-4-sulfonyl)-1,2,3,3a,4,6a-hexahydrocyclopentapyrrole

(1S,3aS,4S,6aS)-1-(Methoxymethoxymethyl)-4-methyl-2-(toluene-4-sulfonyl)hexahydrocyclopentapyrrol-5-one

Downstream raw materials:

methyl [2S-(2α,3β,4β)]-[2-(methoxymethoxy)methyl-4-(1-methylethenyl)-1-(4-methylphenyl)sulfonyl]-3-pyrrolidineacetate

(-)-kainic acid

methyl [2S-(2α,3β,4β)]-[2-(hydroxymethyl)-4-(1-methylethenyl)-1-(4-methylphenyl)sulfonyl]-3-pyrrolidineacetate

(2S,3S,4S)-3-Carboxymethyl-4-isopropenyl-1-(toluene-4-sulfonyl)-pyrrolidine-2-carboxylic acid