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

Base Information

Chemical Name:N-[(1R,2R,5R,6S)-2-(1,3-benzodioxol-5-yl)-5,6-(isopropylidenedioxy)cyclohex-3-en-1-yl]-N-(methoxycarbonyl)-4-methylbenzenesulfonamide
CAS No.:172483-27-1
Molecular Formula:C₂₅H₂₇NO₈S
Molecular Weight:501.557
Hs Code.:

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

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

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

There total 9 articles about N-[(1R,2R,5R,6S)-2-(1,3-benzodioxol-5-yl)-5,6-(isopropylidenedioxy)cyclohex-3-en-1-yl]-N-(methoxycarbonyl)-4-methylbenzenesulfonamide 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:

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

: 172483-27-1
N-[(1R,2R,5R,6S)-2-(1,3-benzodioxol-5-yl)-5,6-(isopropylidenedioxy)cyclohex-3-en-1-yl]-N-(methoxycarbonyl)-4-methylbenzenesulfonamide

Guidance literature:: Multi-step reaction with 4 steps

1: 54 percent / Cu(acac)2 / acetonitrile / 1 h / Ambient temperature

2: 78 percent / Bu₃SnH, AIBN / tetrahydrofuran / 2 h / Heating

3: 1.) n-BuLi, 2.) CuCN, 3.) BF₃*Et₂O

4: 1.) s-BuLi / 1.) THF, 0 deg C, 5 min, 2.) THF, RT, 10 h

With copper acetylacetonate; n-butyllithium; 2,2'-azobis(isobutyronitrile); boron trifluoride diethyl etherate; sec.-butyllithium; tri-n-butyl-tin hydride; In tetrahydrofuran; acetonitrile;
DOI:10.1021/ja960596j

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

: 172483-27-1
N-[(1R,2R,5R,6S)-2-(1,3-benzodioxol-5-yl)-5,6-(isopropylidenedioxy)cyclohex-3-en-1-yl]-N-(methoxycarbonyl)-4-methylbenzenesulfonamide

Guidance literature:: Multi-step reaction with 5 steps

1: p-TsOH*H₂O / acetone / 0.33 h / Ambient temperature

2: 54 percent / Cu(acac)2 / acetonitrile / 1 h / Ambient temperature

3: 78 percent / Bu₃SnH, AIBN / tetrahydrofuran / 2 h / Heating

4: 1.) n-BuLi, 2.) CuCN, 3.) BF₃*Et₂O

5: 1.) s-BuLi / 1.) THF, 0 deg C, 5 min, 2.) THF, RT, 10 h

With copper acetylacetonate; n-butyllithium; 2,2'-azobis(isobutyronitrile); boron trifluoride diethyl etherate; sec.-butyllithium; tri-n-butyl-tin hydride; toluene-4-sulfonic acid; In tetrahydrofuran; acetone; acetonitrile;
DOI:10.1021/ja960596j

Reference yield:

: 163082-04-0
(1R,4S,5S,6R)-3-bromo-4,5-(isopropylidenedioxy)-7-(4'-methylphenylsulfonyl)-7-azabicyclo<4.1.0>hept-2-ene

: 172483-27-1
N-[(1R,2R,5R,6S)-2-(1,3-benzodioxol-5-yl)-5,6-(isopropylidenedioxy)cyclohex-3-en-1-yl]-N-(methoxycarbonyl)-4-methylbenzenesulfonamide

Guidance literature:: Multi-step reaction with 3 steps

1: 78 percent / Bu₃SnH, AIBN / tetrahydrofuran / 2 h / Heating

2: 1.) n-BuLi, 2.) CuCN, 3.) BF₃*Et₂O

3: 1.) s-BuLi / 1.) THF, 0 deg C, 5 min, 2.) THF, RT, 10 h

With n-butyllithium; 2,2'-azobis(isobutyronitrile); boron trifluoride diethyl etherate; sec.-butyllithium; tri-n-butyl-tin hydride; In tetrahydrofuran;
DOI:10.1021/ja960596j