(1R,2R,4aS,11bR)-1-Benzyloxy-2-hydroxy-7-methoxy-5-(4-methoxy-benzyl)-1,4a,5,11b-tetrahydro-2H-[1,3]dioxolo[4,5-j]phenanthridin-6-one

Base Information

• Chemical Name: (1R,2R,4aS,11bR)-1-Benzyloxy-2-hydroxy-7-methoxy-5-(4-methoxy-benzyl)-1,4a,5,11b-tetrahydro-2H-[1,3]dioxolo[4,5-j]phenanthridin-6-one
• CAS No.: 288395-80-2
• Molecular Formula: C₃₀H₂₉NO₇
• Molecular Weight: 515.563

Synonyms:(1R,2R,4aS,11bR)-1-Benzyloxy-2-hydroxy-7-methoxy-5-(4-methoxy-benzyl)-1,4a,5,11b-tetrahydro-2H-[1,3]dioxolo[4,5-j]phenanthridin-6-one

Chemical Property of (1R,2R,4aS,11bR)-1-Benzyloxy-2-hydroxy-7-methoxy-5-(4-methoxy-benzyl)-1,4a,5,11b-tetrahydro-2H-[1,3]dioxolo[4,5-j]phenanthridin-6-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

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Technology Process of (1R,2R,4aS,11bR)-1-Benzyloxy-2-hydroxy-7-methoxy-5-(4-methoxy-benzyl)-1,4a,5,11b-tetrahydro-2H-[1,3]dioxolo[4,5-j]phenanthridin-6-one

There total 23 articles about (1R,2R,4aS,11bR)-1-Benzyloxy-2-hydroxy-7-methoxy-5-(4-methoxy-benzyl)-1,4a,5,11b-tetrahydro-2H-[1,3]dioxolo[4,5-j]phenanthridin-6-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:

(1R,2S,4aS,11bR)-1-Benzyloxy-2-hydroxy-7-methoxy-5-(4-methoxy-benzyl)-3-phenylselanyl-1,3,4,4a,5,11b-hexahydro-2H-[1,3]dioxolo[4,5-j]phenanthridin-6-one → (1R,2R,4aS,11bR)-1-Benzyloxy-2-hydroxy-7-methoxy-5-(4-methoxy-benzyl)-1,4a,5,11b-tetrahydro-2H-[1,3]dioxolo[4,5-j]phenanthridin-6-one (288395-80-2)

Guidance literature:

With dihydrogen peroxide; In ethanol; Heating;

DOI:10.1021/ja000930i

Reference yield:

2H-benzo[d]1,3-dioxolane-4-carbaldehyde (7797-83-3) → (1R,2R,4aS,11bR)-1-Benzyloxy-2-hydroxy-7-methoxy-5-(4-methoxy-benzyl)-1,4a,5,11b-tetrahydro-2H-[1,3]dioxolo[4,5-j]phenanthridin-6-one (288395-80-2)

Guidance literature:

Multi-step reaction with 14 steps

1.1: aq. m-chloroperbenzoic acid / CH₂Cl₂ / 24 h / Heating

1.2: 63 percent / KOH / ethanol / 2 h / 20 °C

2.1: 90 percent / silver trifluoroacetate; Br₂ / CHCl₃ / 1 h / 10 - 15 °C

3.1: 94 percent / pyridinium p-toluenesulfonate / CH₂Cl₂ / 2 h

4.1: n-BuLi / tetrahydrofuran; pentane / 0.5 h / -100 °C

4.2: tetrahydrofuran; toluene; pentane / 0.75 h / -100 °C

5.1: NaH / dimethylformamide / 0.5 h / -5 °C

5.2: dimethylformamide / 0.25 h / -5 °C

6.1: 76 percent / pyridinium p-toluenesulfonate / methanol / 2 h / 20 °C

7.1: 30 percent / benzene / 48 h / 5 °C / UV-irradiation

8.1: NaH / tetrahydrofuran / 0.5 h / 0 °C

8.2: 98 percent / tetrahydrofuran / 24 h / 20 °C

9.1: 85 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.33 h / -5 °C

10.1: 83 percent / Dess-Martin periodinane / CH₂Cl₂ / 4 h

11.1: NaBH₄ / methanol / 0.5 h / -20 °C

12.1: NaH / dimethylformamide / 0.5 h / -20 °C

12.2: 47 mg / tetrabutylammonium iodide / dimethylformamide / 1 h / -10 °C

13.1: NaBH₄ / ethanol / 2 h

14.1: 81 mg / aq. H₂O₂ / ethanol / Heating

With sodium tetrahydroborate; n-butyllithium; tetrabutyl ammonium fluoride; dihydrogen peroxide; bromine; silver trifluoroacetate; pyridinium p-toluenesulfonate; sodium hydride; Dess-Martin periodane; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; methanol; ethanol; dichloromethane; chloroform; N,N-dimethyl-formamide; pentane; benzene; 1.1: Rearrangement / 1.2: Hydrolysis / 2.1: Bromination / 3.1: Addition / 4.1: Metallation / 4.2: Addition / 5.1: Metallation / 5.2: Substitution / 6.1: deprotection / 7.1: Cyclization / 8.1: Metallation / 8.2: Methylation / 9.1: Hydrolysis / 10.1: Oxidation / 11.1: Reduction / 12.1: Metallation / 12.2: Alkylation / 13.1: Ring cleavage / 14.1: oxidative elimination;

DOI:10.1021/ja000930i

Reference yield:

methyl cyclohex-3-ene-1-carboxylate (6493-77-2) → (1R,2R,4aS,11bR)-1-Benzyloxy-2-hydroxy-7-methoxy-5-(4-methoxy-benzyl)-1,4a,5,11b-tetrahydro-2H-[1,3]dioxolo[4,5-j]phenanthridin-6-one (288395-80-2)

Guidance literature:

Multi-step reaction with 18 steps

1.1: N-bromosuccinimide; azobis(isobutyronitrile) / benzene / 0.33 h / Heating

1.2: tri-n-butyltinhydride; azobis(isobutyronitrile) / benzene / 3.5 h / Heating

2.1: O₂; Rose Bengal / acetone / 8 h / -10 °C / Irradiation

2.2: RuCl₂(PPh₃)3 / CH₂Cl₂ / -10 - 20 °C

2.3: 42 percent / NaOMe / methanol / 0.5 h / -5 °C

3.1: 99 percent / Et₃N; 4-dimethylaminopyridine / CH₂Cl₂ / 0 - 20 °C

4.1: 80 percent Turnov_. / cholesterol esterase; aq. NaOH / 36 h / 5 °C / pH 7.7

5.1: 98 percent / imidazole / dimethylformamide / 0.67 h / 20 °C

6.1: 81 percent Turnov_. / LiOH*H₂O / methanol / 48 h / -5 °C

7.1: diphenylphosphorazidate; Et₃N / benzene / 1 h

7.2: toluene / 1 h / 110 °C

8.1: n-BuLi / tetrahydrofuran; pentane / 0.5 h / -100 °C

8.2: tetrahydrofuran; toluene; pentane / 0.75 h / -100 °C

9.1: NaH / dimethylformamide / 0.5 h / -5 °C

9.2: dimethylformamide / 0.25 h / -5 °C

10.1: 76 percent / pyridinium p-toluenesulfonate / methanol / 2 h / 20 °C

11.1: 30 percent / benzene / 48 h / 5 °C / UV-irradiation

12.1: NaH / tetrahydrofuran / 0.5 h / 0 °C

12.2: 98 percent / tetrahydrofuran / 24 h / 20 °C

13.1: 85 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.33 h / -5 °C

14.1: 83 percent / Dess-Martin periodinane / CH₂Cl₂ / 4 h

15.1: NaBH₄ / methanol / 0.5 h / -20 °C

16.1: NaH / dimethylformamide / 0.5 h / -20 °C

16.2: 47 mg / tetrabutylammonium iodide / dimethylformamide / 1 h / -10 °C

17.1: NaBH₄ / ethanol / 2 h

18.1: 81 mg / aq. H₂O₂ / ethanol / Heating

With 1H-imidazole; dmap; lithium hydroxide; sodium hydroxide; sodium tetrahydroborate; N-Bromosuccinimide; n-butyllithium; cholesterol esterase; 2,2'-azobis(isobutyronitrile); diphenyl phosphoryl azide; tetrabutyl ammonium fluoride; dihydrogen peroxide; oxygen; pyridinium p-toluenesulfonate; rose bengal; sodium hydride; Dess-Martin periodane; triethylamine; In tetrahydrofuran; methanol; ethanol; dichloromethane; N,N-dimethyl-formamide; acetone; pentane; benzene; 1.1: Bromination / 1.2: Dehydrobromination / 2.1: Oxidation / 2.2: Epoxidation / 2.3: Ring cleavage / 3.1: Acylation / 4.1: Hydrolysis / 5.1: silylation / 6.1: Hydrolysis / 7.1: azidation / 7.2: Rearrangement / 8.1: Metallation / 8.2: Addition / 9.1: Metallation / 9.2: Substitution / 10.1: deprotection / 11.1: Cyclization / 12.1: Metallation / 12.2: Methylation / 13.1: Hydrolysis / 14.1: Oxidation / 15.1: Reduction / 16.1: Metallation / 16.2: Alkylation / 17.1: Ring cleavage / 18.1: oxidative el;

DOI:10.1021/ja000930i

upstream raw materials:

2H-benzo[d]1,3-dioxolane-4-carbaldehyde

2,3-dihydroxybenzaldehyde

methyl cyclohex-3-ene-1-carboxylate

2,4-Cyclohexadien-1-carbonsaeure-methylester

Downstream raw materials:

(1R,2R,3S,4S,4aR,11bR)-1-benzyloxy-5-(4-methoxy-benzyl)-2,3,4-trihydroxy-7-methoxy-1,3,4,4a,5,11b-hexahydro-2H-[1,3]dioxolo[4,5-j]phenanthridin-6-one

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