N-allyl-N-{(1R,4R,5S)-4,5-isopropylidenedioxycyclopent-2-enyl}-2-nitrobenzenesulfonamide

Base Information

• Chemical Name: N-allyl-N-{(1R,4R,5S)-4,5-isopropylidenedioxycyclopent-2-enyl}-2-nitrobenzenesulfonamide
• CAS No.: 501415-59-4
• Molecular Formula: C₁₇H₂₀N₂O₆S
• Molecular Weight: 380.422
• Mol file: 501415-59-4.mol

Synonyms:N-allyl-N-{(1R,4R,5S)-4,5-isopropylidenedioxycyclopent-2-enyl}-2-nitrobenzenesulfonamide

Chemical Property of N-allyl-N-{(1R,4R,5S)-4,5-isopropylidenedioxycyclopent-2-enyl}-2-nitrobenzenesulfonamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-allyl-N-{(1R,4R,5S)-4,5-isopropylidenedioxycyclopent-2-enyl}-2-nitrobenzenesulfonamide

There total 2 articles about N-allyl-N-{(1R,4R,5S)-4,5-isopropylidenedioxycyclopent-2-enyl}-2-nitrobenzenesulfonamide 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-o-nitrobenzenesulfonamide (65118-17-4) + (-)-carbonic acid (1R,4R,5R)-4,5-isopropylidenedioxycyclopent-2-enyl ester methyl ester (501415-58-3) → N-allyl-N-{(1R,4R,5S)-4,5-isopropylidenedioxycyclopent-2-enyl}-2-nitrobenzenesulfonamide (501415-59-4)

Guidance literature:

With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; (1R,2R)-1,2-bis[(2-diphenylphosphanyl)benzoylamino]cyclohexane; triethylamine; In tetrahydrofuran; at -10 - 0 ℃;

DOI:10.1016/S0040-4020(02)00832-3

Reference yield:

(3aS,4R,6aR)-2,2-dimethyl-2H,3aH,4H,6aH-cyclopenta[d][1,3]-dioxol-4-ol (216015-22-4) → N-allyl-N-{(1R,4R,5S)-4,5-isopropylidenedioxycyclopent-2-enyl}-2-nitrobenzenesulfonamide (501415-59-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 97 percent / CH₂Cl₂; pyridine / 1 h / 0 °C

2: 95 percent / Et₃N; [Pd₂(dba)3]*CHCl₃; (R,R)-N,N'-bis[2-(PPh₂)benzoyl]-1,2-diaminocyclohexane / tetrahydrofuran / -10 - 0 °C

With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; (1R,2R)-1,2-bis[(2-diphenylphosphanyl)benzoylamino]cyclohexane; triethylamine; In tetrahydrofuran; pyridine; dichloromethane;

DOI:10.1016/S0040-4020(02)00832-3

Reference yield:

N-allyl-N-{(1R,4R,5S)-4,5-isopropylidenedioxycyclopent-2-enyl}-2-nitrobenzenesulfonamide (501415-59-4) → N-allyl-N-(4,5-dihydroxy-cyclopent-2-enyl)-2-nitro-benzenesulfonamide

Guidance literature:

With acetic acid; In water; at 80 - 100 ℃;

DOI:10.1016/S0040-4020(02)00832-3

upstream raw materials:

N-allyl-o-nitrobenzenesulfonamide

(-)-carbonic acid (1R,4R,5R)-4,5-isopropylidenedioxycyclopent-2-enyl ester methyl ester

(3aS,4R,6aR)-2,2-dimethyl-2H,3aH,4H,6aH-cyclopenta[d][1,3]-dioxol-4-ol

Downstream raw materials:

acetic acid (1S,2R,5R)-2-acetoxy-5-[allyl-(2-nitrobenzenesulfonyl)-amino]-cyclopent-3-enyl ester

N-allyl-N-{(1R,4R,5S)-4,5-bis-(tert-butyldimethylsilanyloxy)cyclopent-2-enyl}-2-nitrobenzenesulfonamide