(1S,4S,5R)-(+)-4-hexadecyl-5-methoxycarbonyl-1-(4-nitrobenzoyl)-4-trimethylsiloxy-2-cyclopentene

Base Information

• Chemical Name: (1S,4S,5R)-(+)-4-hexadecyl-5-methoxycarbonyl-1-(4-nitrobenzoyl)-4-trimethylsiloxy-2-cyclopentene
• CAS No.: 909410-95-3
• Molecular Formula: C₃₃H₅₃NO₇Si
• Molecular Weight: 603.872
• Mol file: 909410-95-3.mol

Synonyms:(1S,4S,5R)-(+)-4-hexadecyl-5-methoxycarbonyl-1-(4-nitrobenzoyl)-4-trimethylsiloxy-2-cyclopentene

Chemical Property of (1S,4S,5R)-(+)-4-hexadecyl-5-methoxycarbonyl-1-(4-nitrobenzoyl)-4-trimethylsiloxy-2-cyclopentene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,4S,5R)-(+)-4-hexadecyl-5-methoxycarbonyl-1-(4-nitrobenzoyl)-4-trimethylsiloxy-2-cyclopentene

There total 2 articles about (1S,4S,5R)-(+)-4-hexadecyl-5-methoxycarbonyl-1-(4-nitrobenzoyl)-4-trimethylsiloxy-2-cyclopentene 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: 61.0%

(1R,4S,5R)-(-)-4-hexadecyl-1-hydroxy-5-methoxycarbonyl-4-trimethylsiloxy-2-cyclopentene + 4-nitro-benzoic acid (62-23-7) → (1S,4S,5R)-(+)-4-hexadecyl-5-methoxycarbonyl-1-(4-nitrobenzoyl)-4-trimethylsiloxy-2-cyclopentene (909410-95-3)

Guidance literature:

With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; toluene; at 20 ℃; for 0.166667h;

DOI:10.1016/j.tet.2006.06.023

Reference yield:

(4S,5SR)-4-hexadecyl-5-methoxycarbonyl-4-trimethylsiloxy-2-cyclopenten-1-one (852525-54-3) → (1S,4S,5R)-(+)-4-hexadecyl-5-methoxycarbonyl-1-(4-nitrobenzoyl)-4-trimethylsiloxy-2-cyclopentene (909410-95-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 36 percent / diisobutylaluminium hydride / CH₂Cl₂ / 1 h / -78 °C

2: 61 percent / triphenylphosphine; diisopropyl diazodicarboxylate / tetrahydrofuran; toluene / 0.17 h / 20 °C

With di-isopropyl azodicarboxylate; diisobutylaluminium hydride; triphenylphosphine; In tetrahydrofuran; dichloromethane; toluene; 2: Mitsunobu esterification;

DOI:10.1016/j.tet.2006.06.023

upstream raw materials:

4-nitro-benzoic acid

(4S,5SR)-4-hexadecyl-5-methoxycarbonyl-4-trimethylsiloxy-2-cyclopenten-1-one