(3aS,4R,5R,7aR)-5-(1-ethynyl)-2,2-dimethyl-4-[4-methylphenyl(propioloyl)sulfonamido]-3a,4,5,7a-tetrahydro-1,3-benzodioxolone

Base Information

Chemical Name:(3aS,4R,5R,7aR)-5-(1-ethynyl)-2,2-dimethyl-4-[4-methylphenyl(propioloyl)sulfonamido]-3a,4,5,7a-tetrahydro-1,3-benzodioxolone
CAS No.:922178-27-6
Molecular Formula:C₂₁H₂₁NO₅S
Molecular Weight:399.467
Hs Code.:

Synonyms:(3aS,4R,5R,7aR)-5-(1-ethynyl)-2,2-dimethyl-4-[4-methylphenyl(propioloyl)sulfonamido]-3a,4,5,7a-tetrahydro-1,3-benzodioxolone

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Chemical Property of (3aS,4R,5R,7aR)-5-(1-ethynyl)-2,2-dimethyl-4-[4-methylphenyl(propioloyl)sulfonamido]-3a,4,5,7a-tetrahydro-1,3-benzodioxolone

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Technology Process of (3aS,4R,5R,7aR)-5-(1-ethynyl)-2,2-dimethyl-4-[4-methylphenyl(propioloyl)sulfonamido]-3a,4,5,7a-tetrahydro-1,3-benzodioxolone

There total 7 articles about (3aS,4R,5R,7aR)-5-(1-ethynyl)-2,2-dimethyl-4-[4-methylphenyl(propioloyl)sulfonamido]-3a,4,5,7a-tetrahydro-1,3-benzodioxolone 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%

: 922178-20-9
N-[(1R,2R,5R,6S)-2-(2-trimethylsilylethynyl)-5,6-(isopropylidenedioxy)cyclohex-3-en-1-yl]-N-propioloyl-4-methylbenzenesulfonamide

: 922178-27-6
(3aS,4R,5R,7aR)-5-(1-ethynyl)-2,2-dimethyl-4-[4-methylphenyl(propioloyl)sulfonamido]-3a,4,5,7a-tetrahydro-1,3-benzodioxolone

Guidance literature:: With tetrabutylammonium triphenyldifluorosilicate; In acetonitrile; at 20 ℃; for 30h;
DOI:10.1139/V06-078

Reference yield:

: 67451-62-1,82683-92-9,132958-32-8,130792-45-9
cis-(1S,2S)-1,2-dihydroxy-3-bromocyclohexa-3,5-diene

: 922178-27-6
(3aS,4R,5R,7aR)-5-(1-ethynyl)-2,2-dimethyl-4-[4-methylphenyl(propioloyl)sulfonamido]-3a,4,5,7a-tetrahydro-1,3-benzodioxolone

Guidance literature:: Multi-step reaction with 6 steps

1.1: p-toluenesulfonic acid / acetone / 20 °C

2.1: Cu(acac)2 / acetonitrile / 0 - 20 °C

3.1: n-Bu₃SnH; 2,2'-azobisisobutyronitrile / tetrahydrofuran / Heating

4.1: n-BuLi / toluene / 0.17 h / 0 °C

4.2: AlCl₃ / toluene / 18 h / 0 - 20 °C

5.1: 46 percent / n-BuLi / tetrahydrofuran / 0 - 20 °C

6.1: 61 percent / tetrabutylammonium triphenyldifluorosilicate / acetonitrile / 30 h / 20 °C

With n-butyllithium; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; toluene-4-sulfonic acid; tetrabutylammonium triphenyldifluorosilicate; copper acetylacetonate; In tetrahydrofuran; acetone; toluene; acetonitrile;
DOI:10.1139/V06-078

Reference yield:

: 130669-75-9
(3aS,7aS)-4-bromo-2,2-dimethyl-3a,7a-dihydro-1,3-benzodioxole

: 922178-27-6
(3aS,4R,5R,7aR)-5-(1-ethynyl)-2,2-dimethyl-4-[4-methylphenyl(propioloyl)sulfonamido]-3a,4,5,7a-tetrahydro-1,3-benzodioxolone

Guidance literature:: Multi-step reaction with 5 steps

1.1: Cu(acac)2 / acetonitrile / 0 - 20 °C

2.1: n-Bu₃SnH; 2,2'-azobisisobutyronitrile / tetrahydrofuran / Heating

3.1: n-BuLi / toluene / 0.17 h / 0 °C

3.2: AlCl₃ / toluene / 18 h / 0 - 20 °C

4.1: 46 percent / n-BuLi / tetrahydrofuran / 0 - 20 °C

5.1: 61 percent / tetrabutylammonium triphenyldifluorosilicate / acetonitrile / 30 h / 20 °C

With n-butyllithium; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; tetrabutylammonium triphenyldifluorosilicate; copper acetylacetonate; In tetrahydrofuran; toluene; acetonitrile;
DOI:10.1139/V06-078