reutericyclin

Base Information

• Chemical Name: reutericyclin
• CAS No.: 303957-69-9
• Molecular Formula: C₂₀H₃₁NO₄
• Molecular Weight: 349.47
• Mol file: 303957-69-9.mol

Synonyms:(2R)-4-acetyl-1,2-dihydro-5-hydroxy-2-(2-methylpropyl)-1-[(2E)-1-oxodec-2-enyl]-3H-pyrrol-3-one

Chemical Property of reutericyclin

Chemical Property:

Purity/Quality:

99% ^*data from raw suppliers

Reutericyclin 98.11% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of reutericyclin

There total 6 articles about reutericyclin 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: 38.0%

(E)-dec-2-enoyl chloride (110232-46-7) + (2R)-4-acetyl-1,2-dihydro-5-hydroxy-2-(2-methylpropyl)-3H-pyrrol-3-one (875455-92-8) → (2R)-4-acetyl-1,2-dihydro-5-hydroxy-2-(2-methylpropyl)-1-[(2E)-1-oxodec-2-enyl]-3H-pyrrol-3-one (303957-69-9)

Guidance literature:

(2R)-4-acetyl-1,2-dihydro-5-hydroxy-2-(2-methylpropyl)-3H-pyrrol-3-one; With n-butyllithium; In tetrahydrofuran; hexane; at -70 ℃; for 0.666667h;

(E)-dec-2-enoyl chloride; In tetrahydrofuran; hexane; at -70 ℃; for 0.75h;

DOI:10.1002/hlca.200590226

Reference yield:

ethyl N-(acetoacetyl)-D-leucinate (875455-91-7) → (2R)-4-acetyl-1,2-dihydro-5-hydroxy-2-(2-methylpropyl)-1-[(2E)-1-oxodec-2-enyl]-3H-pyrrol-3-one (303957-69-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 68 percent / EtONa / ethanol / 3 h / Heating

2.1: BuLi / hexane; tetrahydrofuran / 0.67 h / -70 °C

2.2: 38 percent / hexane; tetrahydrofuran / 0.75 h / -70 °C

With n-butyllithium; sodium ethanolate; In tetrahydrofuran; ethanol; hexane; 1.1: Dieckmann cyclization;

DOI:10.1002/hlca.200590226

Reference yield:

(R)-leucine (328-38-1,21675-61-6,25248-98-0,70-45-1) → (2R)-4-acetyl-1,2-dihydro-5-hydroxy-2-(2-methylpropyl)-1-[(2E)-1-oxodec-2-enyl]-3H-pyrrol-3-one (303957-69-9)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 87 percent / HCl / Heating

2.1: 94 percent / Et(i-Pr)2N / CH₂Cl₂ / 3 h / 20 °C

3.1: 68 percent / EtONa / ethanol / 3 h / Heating

4.1: BuLi / hexane; tetrahydrofuran / 0.67 h / -70 °C

4.2: 38 percent / hexane; tetrahydrofuran / 0.75 h / -70 °C

With hydrogenchloride; n-butyllithium; sodium ethanolate; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; ethanol; hexane; dichloromethane; 3.1: Dieckmann cyclization;

DOI:10.1002/hlca.200590226

upstream raw materials:

(E)-dec-2-enoyl chloride

(2R)-4-acetyl-1,2-dihydro-5-hydroxy-2-(2-methylpropyl)-3H-pyrrol-3-one

ethyl N-(acetoacetyl)-D-leucinate

(R)-leucine

Downstream raw materials:

D-leucine methyl ester

methyl (E)-dec-2-enoate

(2R)-4-acetyl-1,2-dihydro-5-hydroxy-2-(2-methylpropyl)-3H-pyrrol-3-one

Refernces