allyl-((1R,2S)-2-{[allyl-(4-nitrobenzenesulfonyl)-amino]methyl}cyclopent-3-enyl)-carbamic acid tert-butyl ester

Base Information

• Chemical Name: allyl-((1R,2S)-2-{[allyl-(4-nitrobenzenesulfonyl)-amino]methyl}cyclopent-3-enyl)-carbamic acid tert-butyl ester
• CAS No.: 517907-39-0
• Molecular Formula: C₂₃H₃₁N₃O₆S
• Molecular Weight: 477.582
• Mol file: 517907-39-0.mol

Synonyms:allyl-((1R,2S)-2-{[allyl-(4-nitrobenzenesulfonyl)-amino]methyl}cyclopent-3-enyl)-carbamic acid tert-butyl ester

Chemical Property of allyl-((1R,2S)-2-{[allyl-(4-nitrobenzenesulfonyl)-amino]methyl}cyclopent-3-enyl)-carbamic acid tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of allyl-((1R,2S)-2-{[allyl-(4-nitrobenzenesulfonyl)-amino]methyl}cyclopent-3-enyl)-carbamic acid tert-butyl ester

There total 2 articles about allyl-((1R,2S)-2-{[allyl-(4-nitrobenzenesulfonyl)-amino]methyl}cyclopent-3-enyl)-carbamic acid tert-butyl ester 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: 95.0%

N-allyl-p-nitrobenzenesulfonamide (100704-44-7) + allyl-((1R,2R)-2-hydroxymethylcyclopent-3-enyl)-carbamic acid tert-butyl ester (517907-37-8) → allyl-((1R,2S)-2-{[allyl-(4-nitrobenzenesulfonyl)-amino]methyl}cyclopent-3-enyl)-carbamic acid tert-butyl ester (517907-39-0)

Guidance literature:

With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; at 0 - 20 ℃; for 3.5h;

DOI:10.1021/jo026803h

Reference yield:

allyl-((1R,4R)-4-tributylstannanylmethoxy-cyclopent-2-enyl)-carbamic acid tert-butyl ester → allyl-((1R,2S)-2-{[allyl-(4-nitrobenzenesulfonyl)-amino]methyl}cyclopent-3-enyl)-carbamic acid tert-butyl ester (517907-39-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 69 percent / n-BuLi / tetrahydrofuran; hexane / 12 h / -78 - 20 °C

2: 95 percent / triphenylphosphine; diisopropyl azodicarboxylate / tetrahydrofuran / 3.5 h / 0 - 20 °C

With n-butyllithium; di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; hexane; 1: Wittig-Still rearrangement / 2: Mitsunobu reaction;

DOI:10.1021/jo026803h

Reference yield: 82.0%

allyl-((1R,2S)-2-{[allyl-(4-nitrobenzenesulfonyl)-amino]methyl}cyclopent-3-enyl)-carbamic acid tert-butyl ester (517907-39-0) → (2R,3'S)-1'-(4-nitrobenzenesulfonyl)-3,6,1',2',3',6'-hexahydro-2H-[2,3']bipyridinyl-1-carboxylic acid tert-butyl ester (517907-40-3)

Guidance literature:

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In dichloromethane; for 2h; Heating;

DOI:10.1021/jo026803h

upstream raw materials:

N-allyl-p-nitrobenzenesulfonamide

allyl-((1R,2R)-2-hydroxymethylcyclopent-3-enyl)-carbamic acid tert-butyl ester

Downstream raw materials:

(2R,3'S)-1'-(4-nitrobenzenesulfonyl)-3,6,1',2',3',6'-hexahydro-2H-[2,3']bipyridinyl-1-carboxylic acid tert-butyl ester

(2R,3'S)-1'-(3-phenylprop-2-ynoyl)-[2,3']bipiperidinyl-1-carboxylic acid tert-butyl ester