(1S,2R,3R,4S,5S,6S)-3,4-(isopropylidenedioxy)-5-[(tert-butyldimethylsilyl)oxy]-6-hydroxy-7-(4'-methylphenylsulfonyl)-7-azabicyclo[4.1.0]heptane

Base Information

Chemical Name:(1S,2R,3R,4S,5S,6S)-3,4-(isopropylidenedioxy)-5-[(tert-butyldimethylsilyl)oxy]-6-hydroxy-7-(4'-methylphenylsulfonyl)-7-azabicyclo[4.1.0]heptane
CAS No.:393165-26-9
Molecular Formula:C₂₂H₃₅NO₆SSi
Molecular Weight:469.674
Hs Code.:

Synonyms:(1S,2R,3R,4S,5S,6S)-3,4-(isopropylidenedioxy)-5-[(tert-butyldimethylsilyl)oxy]-6-hydroxy-7-(4'-methylphenylsulfonyl)-7-azabicyclo[4.1.0]heptane

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Chemical Property of (1S,2R,3R,4S,5S,6S)-3,4-(isopropylidenedioxy)-5-[(tert-butyldimethylsilyl)oxy]-6-hydroxy-7-(4'-methylphenylsulfonyl)-7-azabicyclo[4.1.0]heptane

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Technology Process of (1S,2R,3R,4S,5S,6S)-3,4-(isopropylidenedioxy)-5-[(tert-butyldimethylsilyl)oxy]-6-hydroxy-7-(4'-methylphenylsulfonyl)-7-azabicyclo[4.1.0]heptane

There total 9 articles about (1S,2R,3R,4S,5S,6S)-3,4-(isopropylidenedioxy)-5-[(tert-butyldimethylsilyl)oxy]-6-hydroxy-7-(4'-methylphenylsulfonyl)-7-azabicyclo[4.1.0]heptane 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: 74.0%

: 460731-72-0
(1S,2R,3R,4S,5S,6S)-3,4-(isopropylidenedioxy)-5-[(tert-butyldimethylsilyl)oxy]-6-benzoyl-7-(4'-methylphenylsulfonyl)-7-azabicyclo[4.1.0]heptane

: 393165-26-9
(1S,2R,3R,4S,5S,6S)-3,4-(isopropylidenedioxy)-5-[(tert-butyldimethylsilyl)oxy]-6-hydroxy-7-(4'-methylphenylsulfonyl)-7-azabicyclo[4.1.0]heptane

Guidance literature:: With sodium methylate; In tetrahydrofuran; methanol; for 0.166667h;
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

: 393165-26-9
(1S,2R,3R,4S,5S,6S)-3,4-(isopropylidenedioxy)-5-[(tert-butyldimethylsilyl)oxy]-6-hydroxy-7-(4'-methylphenylsulfonyl)-7-azabicyclo[4.1.0]heptane

Guidance literature:: Multi-step reaction with 8 steps

1.1: p-TsOH / acetone

2.1: Cu(acac)2 / acetonitrile

3.1: nBu₃SnH; AIBN / tetrahydrofuran

4.1: 85 percent / RuCl₃*H₂O; NaIO₄ / ethyl acetate; acetonitrile; H₂O / 0 h / 0 - 5 °C

5.1: SO₂Cl₂; NEt₃ / CH₂Cl₂ / 0 - 20 °C

6.1: dimethylformamide / 2 h / 70 °C

6.2: 90 percent / aq. H₂SO₄ / tetrahydrofuran / 1 h

7.1: 85 percent / imidazole / dimethylformamide / 12 h / 20 °C

8.1: 74 percent / NaOMe / methanol; tetrahydrofuran / 0.17 h

With 1H-imidazole; ruthenium trichloride; copper acetylacetonate; sodium periodate; sulfuryl dichloride; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; sodium methylate; toluene-4-sulfonic acid; triethylamine; In tetrahydrofuran; methanol; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; acetone; acetonitrile;
DOI:10.1021/jo020129m

Reference yield:

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

: 393165-26-9
(1S,2R,3R,4S,5S,6S)-3,4-(isopropylidenedioxy)-5-[(tert-butyldimethylsilyl)oxy]-6-hydroxy-7-(4'-methylphenylsulfonyl)-7-azabicyclo[4.1.0]heptane

Guidance literature:: Multi-step reaction with 7 steps

1.1: Cu(acac)2 / acetonitrile

2.1: nBu₃SnH; AIBN / tetrahydrofuran

3.1: 85 percent / RuCl₃*H₂O; NaIO₄ / ethyl acetate; acetonitrile; H₂O / 0 h / 0 - 5 °C

4.1: SO₂Cl₂; NEt₃ / CH₂Cl₂ / 0 - 20 °C

5.1: dimethylformamide / 2 h / 70 °C

5.2: 90 percent / aq. H₂SO₄ / tetrahydrofuran / 1 h

6.1: 85 percent / imidazole / dimethylformamide / 12 h / 20 °C

7.1: 74 percent / NaOMe / methanol; tetrahydrofuran / 0.17 h

With 1H-imidazole; ruthenium trichloride; copper acetylacetonate; sodium periodate; sulfuryl dichloride; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; sodium methylate; triethylamine; In tetrahydrofuran; methanol; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1021/jo020129m