N-benzyl-N-[(1R,2R,3S,4S,5S,6S)-2-(benzo[1,3]dioxolo-5-ylmethoxy)-4,5-(isopropylidenedioxy)-7-oxabicyclo[4.1.0]hept-3-yl]-4-'-methylbenzenesulfonamide

Base Information

Chemical Name:N-benzyl-N-[(1R,2R,3S,4S,5S,6S)-2-(benzo[1,3]dioxolo-5-ylmethoxy)-4,5-(isopropylidenedioxy)-7-oxabicyclo[4.1.0]hept-3-yl]-4-'-methylbenzenesulfonamide
CAS No.:410527-10-5
Molecular Formula:C₃₁H₃₃NO₈S
Molecular Weight:579.671
Hs Code.:

Synonyms:N-benzyl-N-[(1R,2R,3S,4S,5S,6S)-2-(benzo[1,3]dioxolo-5-ylmethoxy)-4,5-(isopropylidenedioxy)-7-oxabicyclo[4.1.0]hept-3-yl]-4-'-methylbenzenesulfonamide

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Chemical Property of N-benzyl-N-[(1R,2R,3S,4S,5S,6S)-2-(benzo[1,3]dioxolo-5-ylmethoxy)-4,5-(isopropylidenedioxy)-7-oxabicyclo[4.1.0]hept-3-yl]-4-'-methylbenzenesulfonamide

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Technology Process of N-benzyl-N-[(1R,2R,3S,4S,5S,6S)-2-(benzo[1,3]dioxolo-5-ylmethoxy)-4,5-(isopropylidenedioxy)-7-oxabicyclo[4.1.0]hept-3-yl]-4-'-methylbenzenesulfonamide

There total 6 articles about N-benzyl-N-[(1R,2R,3S,4S,5S,6S)-2-(benzo[1,3]dioxolo-5-ylmethoxy)-4,5-(isopropylidenedioxy)-7-oxabicyclo[4.1.0]hept-3-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: 71.0%

: 100-39-0
benzyl bromide

: N-[(1aS,2R,3R,3aS,6aS,6bS)-2-(Benzo[1,3]dioxol-5-ylmethoxy)-5,5-dimethyl-hexahydro-1,4,6-trioxa-cyclopropa[e]inden-3-yl]-4-methyl-benzenesulfonamide

: 410527-10-5
N-benzyl-N-[(1R,2R,3S,4S,5S,6S)-2-(benzo[1,3]dioxolo-5-ylmethoxy)-4,5-(isopropylidenedioxy)-7-oxabicyclo[4.1.0]hept-3-yl]-4-'-methylbenzenesulfonamide

Guidance literature:: With tetra-(n-butyl)ammonium iodide; sodium hydride; In tetrahydrofuran; at 20 ℃; for 44h;
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

: 410527-10-5
N-benzyl-N-[(1R,2R,3S,4S,5S,6S)-2-(benzo[1,3]dioxolo-5-ylmethoxy)-4,5-(isopropylidenedioxy)-7-oxabicyclo[4.1.0]hept-3-yl]-4-'-methylbenzenesulfonamide

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

5: KH; 18-crown-6 / 1,2-dimethoxy-ethane / 20 h / 20 °C

6: 71 percent / NaH; Bu₄NI / tetrahydrofuran / 44 h / 20 °C

With copper acetylacetonate; 18-crown-6 ether; 2,2'-azobis(isobutyronitrile); 6,6'-di-tert-butyl-4,4'-thiodi-o-cresol; tri-n-butyl-tin hydride; tetra-(n-butyl)ammonium iodide; potassium hydride; sodium hydride; toluene-4-sulfonic acid; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; 1,2-dimethoxyethane; 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

: 410527-10-5
N-benzyl-N-[(1R,2R,3S,4S,5S,6S)-2-(benzo[1,3]dioxolo-5-ylmethoxy)-4,5-(isopropylidenedioxy)-7-oxabicyclo[4.1.0]hept-3-yl]-4-'-methylbenzenesulfonamide

Guidance literature:: Multi-step reaction with 5 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

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

5: 71 percent / NaH; Bu₄NI / tetrahydrofuran / 44 h / 20 °C

With copper acetylacetonate; 18-crown-6 ether; 2,2'-azobis(isobutyronitrile); 6,6'-di-tert-butyl-4,4'-thiodi-o-cresol; tri-n-butyl-tin hydride; tetra-(n-butyl)ammonium iodide; potassium hydride; sodium hydride; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; 1,2-dimethoxyethane; 1,2-dichloro-ethane; acetonitrile;
DOI:10.1139/v01-139