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

Base Information

Chemical Name:(1R,2S,3S,4S,4aR,11bS)-1,2,3,4,4a,11b-hexahydro-1-hydroxy-2-[(tert-butyldimethylsilyl)oxy]-3,4-(isopropylidenedioxy)-5-N-(4'-methylphenylsulfonyl)-[1,3]dioxolo[4,5-j]phenanthridin
CAS No.:393165-28-1
Molecular Formula:C₃₀H₄₁NO₈SSi
Molecular Weight:603.809
Hs Code.:

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

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

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

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

There total 10 articles about (1R,2S,3S,4S,4aR,11bS)-1,2,3,4,4a,11b-hexahydro-1-hydroxy-2-[(tert-butyldimethylsilyl)oxy]-3,4-(isopropylidenedioxy)-5-N-(4'-methylphenylsulfonyl)-[1,3]dioxolo[4,5-j]phenanthridin 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: 68.0%

: 393165-27-0
(1R,2R,3S,4S,5S,6R)-4,5-(isopropylidenedioxy)-3-[(tert-butyldimethylsilyl)oxy]-6-N-(3',4'-methylenedioxybenzyl)-N-(4'-methylphenylsulfonyl)-7-oxabicyclo[4.1.0]heptane

: 393165-28-1
(1R,2S,3S,4S,4aR,11bS)-1,2,3,4,4a,11b-hexahydro-1-hydroxy-2-[(tert-butyldimethylsilyl)oxy]-3,4-(isopropylidenedioxy)-5-N-(4'-methylphenylsulfonyl)-[1,3]dioxolo[4,5-j]phenanthridin

Guidance literature:: With dimethylaluminum chloride; In dichloromethane; at -30 - 0 ℃; for 2h;
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

: 393165-28-1
(1R,2S,3S,4S,4aR,11bS)-1,2,3,4,4a,11b-hexahydro-1-hydroxy-2-[(tert-butyldimethylsilyl)oxy]-3,4-(isopropylidenedioxy)-5-N-(4'-methylphenylsulfonyl)-[1,3]dioxolo[4,5-j]phenanthridin

Guidance literature:: Multi-step reaction with 10 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

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; In tetrahydrofuran; methanol; 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

: 393165-28-1
(1R,2S,3S,4S,4aR,11bS)-1,2,3,4,4a,11b-hexahydro-1-hydroxy-2-[(tert-butyldimethylsilyl)oxy]-3,4-(isopropylidenedioxy)-5-N-(4'-methylphenylsulfonyl)-[1,3]dioxolo[4,5-j]phenanthridin

Guidance literature:: Multi-step reaction with 9 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

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; In tetrahydrofuran; methanol; hexane; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; acetonitrile; 8.1: aza-Payne rearrangement;
DOI:10.1021/jo020129m