(1R,2R,3S,4S,5S,6S)-3,4-dihydroxy-5,6-(isopropylidenedioxy)-2-(3',4'-methylenedioxyphenylmethyl)-1-cyclohexylbenzenesulfonamide

Base Information

Chemical Name:(1R,2R,3S,4S,5S,6S)-3,4-dihydroxy-5,6-(isopropylidenedioxy)-2-(3',4'-methylenedioxyphenylmethyl)-1-cyclohexylbenzenesulfonamide
CAS No.:410527-56-9
Molecular Formula:C₃₁H₃₅NO₉S
Molecular Weight:597.686
Hs Code.:

Synonyms:(1R,2R,3S,4S,5S,6S)-3,4-dihydroxy-5,6-(isopropylidenedioxy)-2-(3',4'-methylenedioxyphenylmethyl)-1-cyclohexylbenzenesulfonamide

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Chemical Property of (1R,2R,3S,4S,5S,6S)-3,4-dihydroxy-5,6-(isopropylidenedioxy)-2-(3',4'-methylenedioxyphenylmethyl)-1-cyclohexylbenzenesulfonamide

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Technology Process of (1R,2R,3S,4S,5S,6S)-3,4-dihydroxy-5,6-(isopropylidenedioxy)-2-(3',4'-methylenedioxyphenylmethyl)-1-cyclohexylbenzenesulfonamide

There total 6 articles about (1R,2R,3S,4S,5S,6S)-3,4-dihydroxy-5,6-(isopropylidenedioxy)-2-(3',4'-methylenedioxyphenylmethyl)-1-cyclohexylbenzenesulfonamide 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: 66.0%

: 410527-53-6
N-benzyl-N-[(1R,2S,5R,6S)-2-(benzo[1,3-dioxol-5-yl]methoxy)-5,6-(isopropylidenedioxy)cyclohex-3-enyl]-4'-methylbenzenesulfonamide

: 410527-56-9
(1R,2R,3S,4S,5S,6S)-3,4-dihydroxy-5,6-(isopropylidenedioxy)-2-(3',4'-methylenedioxyphenylmethyl)-1-cyclohexylbenzenesulfonamide

Guidance literature:: With sodium periodate; ruthenium trichloride; In ethyl acetate; acetonitrile; at 0 ℃; for 0.05h;
DOI:10.1139/v01-139

Reference yield:

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

: 410527-56-9
(1R,2R,3S,4S,5S,6S)-3,4-dihydroxy-5,6-(isopropylidenedioxy)-2-(3',4'-methylenedioxyphenylmethyl)-1-cyclohexylbenzenesulfonamide

Guidance literature:: Multi-step reaction with 5 steps

1: Cu(acac)2 / acetonitrile / 20 °C

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

3: 56 percent / KH; 18-crown-6 / 1,2-dimethoxy-ethane / 24 h / 20 °C

4: 84 percent / NaH; Bu₄NI / tetrahydrofuran / 18 h / 20 °C

5: 66 percent / NaIO₄ / RuCl₃*3H₂O / acetonitrile; ethyl acetate / 0.05 h / 0 °C

With copper acetylacetonate; sodium periodate; 18-crown-6 ether; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; tetra-(n-butyl)ammonium iodide; potassium hydride; sodium hydride; ruthenium trichloride; In tetrahydrofuran; 1,2-dimethoxyethane; ethyl acetate; acetonitrile;
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

: 410527-56-9
(1R,2R,3S,4S,5S,6S)-3,4-dihydroxy-5,6-(isopropylidenedioxy)-2-(3',4'-methylenedioxyphenylmethyl)-1-cyclohexylbenzenesulfonamide

Guidance literature:: Multi-step reaction with 6 steps

1: p-TSA / acetone / 20 °C

2: Cu(acac)2 / acetonitrile / 20 °C

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

4: 56 percent / KH; 18-crown-6 / 1,2-dimethoxy-ethane / 24 h / 20 °C

5: 84 percent / NaH; Bu₄NI / tetrahydrofuran / 18 h / 20 °C

6: 66 percent / NaIO₄ / RuCl₃*3H₂O / acetonitrile; ethyl acetate / 0.05 h / 0 °C

With copper acetylacetonate; sodium periodate; 18-crown-6 ether; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; tetra-(n-butyl)ammonium iodide; potassium hydride; sodium hydride; toluene-4-sulfonic acid; ruthenium trichloride; In tetrahydrofuran; 1,2-dimethoxyethane; ethyl acetate; acetone; acetonitrile;
DOI:10.1139/v01-139