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

Base Information

Chemical Name:N-[(1R,2R,3S,4S,5S,6S)-2-(1,3-benzodioxol-5-yl)-3,4-dihydroxy-5,6-(isopropylidenedioxy)cyclohex-1-yl]-4-methylbenzenesulfonamide
CAS No.:460731-73-1
Molecular Formula:C₂₃H₂₇NO₈S
Molecular Weight:477.535
Hs Code.:

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

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

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

There total 4 articles about N-[(1R,2R,3S,4S,5S,6S)-2-(1,3-benzodioxol-5-yl)-3,4-dihydroxy-5,6-(isopropylidenedioxy)cyclohex-1-yl]-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: 75.0%

: 172483-26-0
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

: 460731-73-1
N-[(1R,2R,3S,4S,5S,6S)-2-(1,3-benzodioxol-5-yl)-3,4-dihydroxy-5,6-(isopropylidenedioxy)cyclohex-1-yl]-4-methylbenzenesulfonamide

Guidance literature:: With ruthenium trichloride; sodium periodate; In ethyl acetate; acetonitrile; at 0 ℃; for 0.05h;
DOI:10.1021/jo020129m

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

: 460731-73-1
N-[(1R,2R,3S,4S,5S,6S)-2-(1,3-benzodioxol-5-yl)-3,4-dihydroxy-5,6-(isopropylidenedioxy)cyclohex-1-yl]-4-methylbenzenesulfonamide

Guidance literature:: Multi-step reaction with 5 steps

1: p-TsOH / acetone

2: Cu(acac)2 / acetonitrile

3: nBu₃SnH; AIBN / tetrahydrofuran

4: 21 percent / Lewis acid

5: 75 percent / aq. NaIO₄; RuCl₃*H₂O / acetonitrile; ethyl acetate / 0.05 h / 0 °C

With ruthenium trichloride; copper acetylacetonate; sodium periodate; 2,2'-azobis(isobutyronitrile); Lewis acid; tri-n-butyl-tin hydride; toluene-4-sulfonic acid; In tetrahydrofuran; ethyl acetate; acetone; acetonitrile;
DOI:10.1021/jo020129m

Reference yield:

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

: 460731-73-1
N-[(1R,2R,3S,4S,5S,6S)-2-(1,3-benzodioxol-5-yl)-3,4-dihydroxy-5,6-(isopropylidenedioxy)cyclohex-1-yl]-4-methylbenzenesulfonamide

Guidance literature:: Multi-step reaction with 4 steps

1: Cu(acac)2 / acetonitrile

2: nBu₃SnH; AIBN / tetrahydrofuran

3: 21 percent / Lewis acid

4: 75 percent / aq. NaIO₄; RuCl₃*H₂O / acetonitrile; ethyl acetate / 0.05 h / 0 °C

With ruthenium trichloride; copper acetylacetonate; sodium periodate; 2,2'-azobis(isobutyronitrile); Lewis acid; tri-n-butyl-tin hydride; In tetrahydrofuran; ethyl acetate; acetonitrile;
DOI:10.1021/jo020129m