(1R,2S,3S,4S,4aR,11bS)-1,2,3,4,4a,11b-hexahydro-1-methoxymethyl-2-[(tert-butyldimethylsilyl)oxy]-3,4-(isopropylidenedioxy)-5-N-(4'-methylphenylsulfonyl)-[1,3]dioxolo[4,5-j]phenanthridin-6(2H)-one

Base Information

Chemical Name:(1R,2S,3S,4S,4aR,11bS)-1,2,3,4,4a,11b-hexahydro-1-methoxymethyl-2-[(tert-butyldimethylsilyl)oxy]-3,4-(isopropylidenedioxy)-5-N-(4'-methylphenylsulfonyl)-[1,3]dioxolo[4,5-j]phenanthridin-6(2H)-one
CAS No.:393165-30-5
Molecular Formula:C₃₂H₄₃NO₁₀SSi
Molecular Weight:661.846
Hs Code.:

(1R,2S,3S,4S,4aR,11bS)-1,2,3,4,4a,11b-hexahydro-1-methoxymethyl-2-[(tert-butyldimethylsilyl)oxy]-3,4-(isopropylidenedioxy)-5-N-(4'-methylphenylsulfonyl)-[1,3]dioxolo[4,5-j]phenanthridin-6(2H)-one

Synonyms:(1R,2S,3S,4S,4aR,11bS)-1,2,3,4,4a,11b-hexahydro-1-methoxymethyl-2-[(tert-butyldimethylsilyl)oxy]-3,4-(isopropylidenedioxy)-5-N-(4'-methylphenylsulfonyl)-[1,3]dioxolo[4,5-j]phenanthridin-6(2H)-one

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Chemical Property of (1R,2S,3S,4S,4aR,11bS)-1,2,3,4,4a,11b-hexahydro-1-methoxymethyl-2-[(tert-butyldimethylsilyl)oxy]-3,4-(isopropylidenedioxy)-5-N-(4'-methylphenylsulfonyl)-[1,3]dioxolo[4,5-j]phenanthridin-6(2H)-one

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Technology Process of (1R,2S,3S,4S,4aR,11bS)-1,2,3,4,4a,11b-hexahydro-1-methoxymethyl-2-[(tert-butyldimethylsilyl)oxy]-3,4-(isopropylidenedioxy)-5-N-(4'-methylphenylsulfonyl)-[1,3]dioxolo[4,5-j]phenanthridin-6(2H)-one

There total 13 articles about (1R,2S,3S,4S,4aR,11bS)-1,2,3,4,4a,11b-hexahydro-1-methoxymethyl-2-[(tert-butyldimethylsilyl)oxy]-3,4-(isopropylidenedioxy)-5-N-(4'-methylphenylsulfonyl)-[1,3]dioxolo[4,5-j]phenanthridin-6(2H)-one 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: 50.0%

: 393165-29-2
(1R,2S,3S,4S,4aR,11bS)-1,2,3,4,4a,11b-hexahydro-1-methoxymethyl-2-[(tert-butyldimethylsilyl)oxy]-3,4-(isopropylidenedioxy)-5-N-(4'-methylphenylsulfonyl)-[1,3]dioxolo[4,5-j]phenanthridin

: 393165-30-5
(1R,2S,3S,4S,4aR,11bS)-1,2,3,4,4a,11b-hexahydro-1-methoxymethyl-2-[(tert-butyldimethylsilyl)oxy]-3,4-(isopropylidenedioxy)-5-N-(4'-methylphenylsulfonyl)-[1,3]dioxolo[4,5-j]phenanthridin-6(2H)-one

Guidance literature:: With ruthenium trichloride; sodium periodate; In tetrachloromethane; water; acetonitrile; at 20 ℃; for 0.5h;
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

: 393165-30-5
(1R,2S,3S,4S,4aR,11bS)-1,2,3,4,4a,11b-hexahydro-1-methoxymethyl-2-[(tert-butyldimethylsilyl)oxy]-3,4-(isopropylidenedioxy)-5-N-(4'-methylphenylsulfonyl)-[1,3]dioxolo[4,5-j]phenanthridin-6(2H)-one

Guidance literature:: Multi-step reaction with 12 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

9.1: n-BuLi / tetrahydrofuran; hexane / -78 - -30 °C

9.2: 68 percent / Bu₄NI / tetrahydrofuran / -30 - 20 °C

10.1: 68 percent / Me₂AlCl / CH₂Cl₂ / 2 h / -30 - 0 °C

11.1: 97 percent / Huenig's base / 12 h / 20 °C

12.1: 50 percent / NaIO₄; RuCl₃*H₂O / acetonitrile; CCl₄; H₂O / 0.5 h / 20 °C

With 1H-imidazole; ruthenium trichloride; copper acetylacetonate; sodium periodate; n-butyllithium; sulfuryl dichloride; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; sodium methylate; dimethylaluminum chloride; toluene-4-sulfonic acid; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; tetrachloromethane; hexane; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; acetone; acetonitrile; 9.1: aza-Payne rearrangement;
DOI:10.1021/jo020129m

Reference yield:

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

: 393165-30-5
(1R,2S,3S,4S,4aR,11bS)-1,2,3,4,4a,11b-hexahydro-1-methoxymethyl-2-[(tert-butyldimethylsilyl)oxy]-3,4-(isopropylidenedioxy)-5-N-(4'-methylphenylsulfonyl)-[1,3]dioxolo[4,5-j]phenanthridin-6(2H)-one

Guidance literature:: Multi-step reaction with 11 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

8.1: n-BuLi / tetrahydrofuran; hexane / -78 - -30 °C

8.2: 68 percent / Bu₄NI / tetrahydrofuran / -30 - 20 °C

9.1: 68 percent / Me₂AlCl / CH₂Cl₂ / 2 h / -30 - 0 °C

10.1: 97 percent / Huenig's base / 12 h / 20 °C

11.1: 50 percent / NaIO₄; RuCl₃*H₂O / acetonitrile; CCl₄; H₂O / 0.5 h / 20 °C

With 1H-imidazole; ruthenium trichloride; copper acetylacetonate; sodium periodate; n-butyllithium; sulfuryl dichloride; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; sodium methylate; dimethylaluminum chloride; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; tetrachloromethane; hexane; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; acetonitrile; 8.1: aza-Payne rearrangement;
DOI:10.1021/jo020129m