N-((3aS,4R,5R,7aR)-2,2-Dimethyl-3a,4,5,7a-tetrahydro-[5,5']bi[benzo[1,3]dioxolyl]-4-yl)-4-methyl-benzenesulfonamide

Base Information

• Chemical Name: N-((3aS,4R,5R,7aR)-2,2-Dimethyl-3a,4,5,7a-tetrahydro-[5,5']bi[benzo[1,3]dioxolyl]-4-yl)-4-methyl-benzenesulfonamide
• CAS No.: 172483-26-0
• Molecular Formula: C₂₃H₂₅NO₆S
• Molecular Weight: 443.521
• Mol file: 172483-26-0.mol

Synonyms:N-((3aS,4R,5R,7aR)-2,2-Dimethyl-3a,4,5,7a-tetrahydro-[5,5']bi[benzo[1,3]dioxolyl]-4-yl)-4-methyl-benzenesulfonamide

Chemical Property of N-((3aS,4R,5R,7aR)-2,2-Dimethyl-3a,4,5,7a-tetrahydro-[5,5']bi[benzo[1,3]dioxolyl]-4-yl)-4-methyl-benzenesulfonamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-((3aS,4R,5R,7aR)-2,2-Dimethyl-3a,4,5,7a-tetrahydro-[5,5']bi[benzo[1,3]dioxolyl]-4-yl)-4-methyl-benzenesulfonamide

There total 8 articles about N-((3aS,4R,5R,7aR)-2,2-Dimethyl-3a,4,5,7a-tetrahydro-[5,5']bi[benzo[1,3]dioxolyl]-4-yl)-4-methyl-benzenesulfonamide 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: 21.0%

1,2-(methylenedioxy)-4-bromobenzene (2635-13-4) + (1R,4R,5S,6R)-4,5-(isopropylidenedioxy)-7-(4'-methylphenylsulfonyl)-7-azabicyclo<4.1.0>hept-2-ene (160309-18-2) → N-((3aS,4R,5R,7aR)-2,2-Dimethyl-3a,4,5,7a-tetrahydro-[5,5']bi[benzo[1,3]dioxolyl]-4-yl)-4-methyl-benzenesulfonamide (172483-26-0)

Guidance literature:

With Lewis acid;

DOI:10.1021/jo020129m

Reference yield:

cis-(1S,2S)-1,2-dihydroxy-3-bromocyclohexa-3,5-diene (67451-62-1,82683-92-9,132958-32-8,130792-45-9) → N-((3aS,4R,5R,7aR)-2,2-Dimethyl-3a,4,5,7a-tetrahydro-[5,5']bi[benzo[1,3]dioxolyl]-4-yl)-4-methyl-benzenesulfonamide (172483-26-0)

Guidance literature:

Multi-step reaction with 4 steps

1: p-TsOH / acetone

2: Cu(acac)2 / acetonitrile

3: nBu₃SnH; AIBN / tetrahydrofuran

4: 21 percent / Lewis acid

With copper acetylacetonate; 2,2'-azobis(isobutyronitrile); Lewis acid; tri-n-butyl-tin hydride; toluene-4-sulfonic acid; In tetrahydrofuran; acetone; acetonitrile;

DOI:10.1021/jo020129m

Reference yield:

(3aS,7aS)-4-bromo-2,2-dimethyl-3a,7a-dihydro-1,3-benzodioxole (130669-75-9) → N-((3aS,4R,5R,7aR)-2,2-Dimethyl-3a,4,5,7a-tetrahydro-[5,5']bi[benzo[1,3]dioxolyl]-4-yl)-4-methyl-benzenesulfonamide (172483-26-0)

Guidance literature:

Multi-step reaction with 3 steps

1: Cu(acac)2 / acetonitrile

2: nBu₃SnH; AIBN / tetrahydrofuran

3: 21 percent / Lewis acid

With copper acetylacetonate; 2,2'-azobis(isobutyronitrile); Lewis acid; tri-n-butyl-tin hydride; In tetrahydrofuran; acetonitrile;

DOI:10.1021/jo020129m

upstream raw materials:

1,2-(methylenedioxy)-4-bromobenzene

(1R,4R,5S,6R)-4,5-(isopropylidenedioxy)-7-(4'-methylphenylsulfonyl)-7-azabicyclo<4.1.0>hept-2-ene

cis-(1S,2S)-1,2-dihydroxy-3-bromocyclohexa-3,5-diene

(3aS,7aS)-4-bromo-2,2-dimethyl-3a,7a-dihydro-1,3-benzodioxole

Downstream raw materials:

N-[(1R,2R,5R,6S)-2-(1,3-benzodioxol-5-yl)-5,6-(isopropylidenedioxy)cyclohex-3-en-1-yl]-N-(methoxycarbonyl)-4-methylbenzenesulfonamide

Acetic acid (1R,2S,3S,4S,5R,6R)-2,3,4-triacetoxy-6-benzo[1,3]dioxol-5-yl-5-methoxycarbonylamino-cyclohexyl ester

((1R,2R,3R,4S,5S,6S)-2-Benzo[1,3]dioxol-5-yl-3,4,5,6-tetrahydroxy-cyclohexyl)-carbamic acid methyl ester

((1R,2R,5R,6S)-2-Benzo[1,3]dioxol-5-yl-5,6-dihydroxy-cyclohex-3-enyl)-carbamic acid methyl ester