(2S,4R,5S,6S)-5,6-(isopropylidenedioxy)-3-(4'-methylphenylsulfonyl)-8-oxa-3-azatricyclo[5.1.0.0]octane

Base Information

Chemical Name:(2S,4R,5S,6S)-5,6-(isopropylidenedioxy)-3-(4'-methylphenylsulfonyl)-8-oxa-3-azatricyclo[5.1.0.0]octane
CAS No.:393165-22-5
Molecular Formula:C₁₆H₁₉NO₅S
Molecular Weight:337.397
Hs Code.:

Synonyms:(2S,4R,5S,6S)-5,6-(isopropylidenedioxy)-3-(4'-methylphenylsulfonyl)-8-oxa-3-azatricyclo[5.1.0.0]octane

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Chemical Property of (2S,4R,5S,6S)-5,6-(isopropylidenedioxy)-3-(4'-methylphenylsulfonyl)-8-oxa-3-azatricyclo[5.1.0.0]octane

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Technology Process of (2S,4R,5S,6S)-5,6-(isopropylidenedioxy)-3-(4'-methylphenylsulfonyl)-8-oxa-3-azatricyclo[5.1.0.0]octane

There total 4 articles about (2S,4R,5S,6S)-5,6-(isopropylidenedioxy)-3-(4'-methylphenylsulfonyl)-8-oxa-3-azatricyclo[5.1.0.0]octane 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: 80.0%

: 160309-18-2
(1R,4R,5S,6R)-4,5-(isopropylidenedioxy)-7-(4'-methylphenylsulfonyl)-7-azabicyclo<4.1.0>hept-2-ene

: 393165-22-5
(2S,4R,5S,6S)-5,6-(isopropylidenedioxy)-3-(4'-methylphenylsulfonyl)-8-oxa-3-azatricyclo[5.1.0.0]octane

Guidance literature:: With 6,6'-di-tert-butyl-4,4'-thiodi-o-cresol; 3-chloro-benzenecarboperoxoic acid; In 1,2-dichloro-ethane; for 12h; Heating;
DOI:10.1139/v01-139

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

: 393165-22-5
(2S,4R,5S,6S)-5,6-(isopropylidenedioxy)-3-(4'-methylphenylsulfonyl)-8-oxa-3-azatricyclo[5.1.0.0]octane

Guidance literature:: Multi-step reaction with 4 steps

1: p-TSA / acetone / 20 °C

2: Cu(acac)2 / acetonitrile / 20 °C

3: 78 percent / Bu₃SnH; AIBN / tetrahydrofuran / Heating

4: 80 percent / mCPBA; 3-tert-butyl-4-hydroxy-5-methylphenyl sulfide / 1,2-dichloro-ethane / 12 h / Heating

With copper acetylacetonate; 2,2'-azobis(isobutyronitrile); 6,6'-di-tert-butyl-4,4'-thiodi-o-cresol; tri-n-butyl-tin hydride; toluene-4-sulfonic acid; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; 1,2-dichloro-ethane; acetone; acetonitrile;
DOI:10.1139/v01-139

Reference yield:

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

: 393165-22-5
(2S,4R,5S,6S)-5,6-(isopropylidenedioxy)-3-(4'-methylphenylsulfonyl)-8-oxa-3-azatricyclo[5.1.0.0]octane

Guidance literature:: Multi-step reaction with 3 steps

1: Cu(acac)2 / acetonitrile / 20 °C

2: 78 percent / Bu₃SnH; AIBN / tetrahydrofuran / Heating

3: 80 percent / mCPBA; 3-tert-butyl-4-hydroxy-5-methylphenyl sulfide / 1,2-dichloro-ethane / 12 h / Heating

With copper acetylacetonate; 2,2'-azobis(isobutyronitrile); 6,6'-di-tert-butyl-4,4'-thiodi-o-cresol; tri-n-butyl-tin hydride; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; 1,2-dichloro-ethane; acetonitrile;
DOI:10.1139/v01-139