(+)-4(R)-acetoxy-1-<5-(benzyloxy)-2,2-dimethylpent-3-(E)-en-1-yl>-2,5-pyrrolidinedione

Base Information

• Chemical Name: (+)-4(R)-acetoxy-1-<5-(benzyloxy)-2,2-dimethylpent-3-(E)-en-1-yl>-2,5-pyrrolidinedione
• CAS No.: 86534-22-7
• Molecular Formula: C₂₀H₂₅NO₅
• Molecular Weight: 359.422
• Mol file: 86534-22-7.mol

Synonyms:(+)-4(R)-acetoxy-1-<5-(benzyloxy)-2,2-dimethylpent-3-(E)-en-1-yl>-2,5-pyrrolidinedione

Chemical Property of (+)-4(R)-acetoxy-1-<5-(benzyloxy)-2,2-dimethylpent-3-(E)-en-1-yl>-2,5-pyrrolidinedione

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (+)-4(R)-acetoxy-1-<5-(benzyloxy)-2,2-dimethylpent-3-(E)-en-1-yl>-2,5-pyrrolidinedione

There total 12 articles about (+)-4(R)-acetoxy-1-<5-(benzyloxy)-2,2-dimethylpent-3-(E)-en-1-yl>-2,5-pyrrolidinedione 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: 81.0%

(R)-(+)-2-acetoxysuccinic anhydride (14189-99-2,24766-96-9,59025-03-5,79814-40-7) + 5-(benzyloxy)-2,2-dimethylpent-3(E)-enamine (86534-21-6) → (+)-4(R)-acetoxy-1-<5-(benzyloxy)-2,2-dimethylpent-3-(E)-en-1-yl>-2,5-pyrrolidinedione (86534-22-7)

Guidance literature:

With acetyl chloride; In dichloromethane; 1) reflux, 2) 40 degC;

DOI:10.1039/c39830000135

Reference yield:

(R)-3-Acetoxy-N-((E)-5-benzyloxy-2,2-dimethyl-pent-3-enyl)-succinamic acid (94162-50-2) + (R)-2-Acetoxy-N-((E)-5-benzyloxy-2,2-dimethyl-pent-3-enyl)-succinamic acid (94202-33-2) → (+)-4(R)-acetoxy-1-<5-(benzyloxy)-2,2-dimethylpent-3-(E)-en-1-yl>-2,5-pyrrolidinedione (86534-22-7)

Guidance literature:

With acetyl chloride; In dichloromethane; at 40 ℃; for 30h; Yield given;

DOI:10.1021/jo00202a016

Reference yield:

6-(benzyloxy)-3,3-dimethyl-4-hexenoyl chloride (86534-20-5) → (+)-4(R)-acetoxy-1-<5-(benzyloxy)-2,2-dimethylpent-3-(E)-en-1-yl>-2,5-pyrrolidinedione (86534-22-7)

Guidance literature:

Multi-step reaction with 2 steps

2: 81 percent / 2) AcCl / CH₂Cl₂ / 1) reflux, 2) 40 degC

With acetyl chloride; In dichloromethane;

DOI:10.1039/c39830000135

upstream raw materials:

(R)-(+)-2-acetoxysuccinic anhydride

5-(benzyloxy)-2,2-dimethylpent-3(E)-enamine

(R)-3-Acetoxy-N-((E)-5-benzyloxy-2,2-dimethyl-pent-3-enyl)-succinamic acid

(R)-2-Acetoxy-N-((E)-5-benzyloxy-2,2-dimethyl-pent-3-enyl)-succinamic acid

Downstream raw materials:

(+)-1(S)-acetoxy-7(S)-<(benzyloxy)methyl>-6(R)-(2-hydroxyprop-2-yl)-7a(R)-hexahydro-3H-pyrrolizin-3-one

1(S)-acetoxy-6(R)-(2-formyloxyprop-2-yl)-7(S)-<(benzyloxy)methyl>-7a(R)-hexahydro-3H-pyrrolizin-3-one

4(R)-acetoxy-1-<5-(benzyloxy)-2,2-dimethylpent-3(E)-en-1yl>-5-hydroxy-2-pyrrolidinone

(+)-7(S)-<(benzyloxy)methyl>-1(R)-hydroxy-6(S)-(2-hydroxyprop-2-yl)-7a(R)-hexahydro-3H-pyrrolizin-3-one