(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

Base Information

Chemical Name:(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
CAS No.:288395-81-3
Molecular Formula:C₃₀H₃₁NO₉
Molecular Weight:549.577
Hs Code.:

Synonyms:(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

Suppliers and Price of (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

Supply Marketing:

Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

Manufacturers and distributors:

Manufacture/Brand
Chemicals and raw materials
Packaging
price

Total 0 raw suppliers

Chemical Property of (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

Chemical Property:

Purity/Quality:

Safty Information:

Pictogram(s):
Hazard Codes:

MSDS Files:

Useful:

Technology Process of (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

There total 24 articles about (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 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: 89.0%

: 288395-80-2
(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

: 288395-81-3
(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

Guidance literature:: With pyridine; water; acetone; osmium(VIII) oxide; In tetrahydrofuran; tert-butyl alcohol; for 4h;
DOI:10.1021/ja000930i

Reference yield:

: 7797-83-3
2H-benzo[d]1,3-dioxolane-4-carbaldehyde

: 288395-81-3
(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

Guidance literature:: Multi-step reaction with 15 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

15.1: 89 percent / pyridine; acetone; H₂O / OsO₄ / 2-methyl-propan-2-ol; tetrahydrofuran / 4 h

With pyridine; sodium tetrahydroborate; n-butyllithium; tetrabutyl ammonium fluoride; water; dihydrogen peroxide; bromine; silver trifluoroacetate; pyridinium p-toluenesulfonate; sodium hydride; Dess-Martin periodane; 3-chloro-benzenecarboperoxoic acid; acetone; osmium(VIII) oxide; In tetrahydrofuran; methanol; ethanol; dichloromethane; chloroform; N,N-dimethyl-formamide; tert-butyl alcohol; 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 / 15.1: dihydroxylation;
DOI:10.1021/ja000930i

Reference yield:

: 24677-78-9
2,3-dihydroxybenzaldehyde

: 288395-81-3
(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

Guidance literature:: Multi-step reaction with 16 steps

1.1: 84 percent / K₂CO₃; CuO / dimethylformamide / 8 h / Heating

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

2.2: 63 percent / KOH / ethanol / 2 h / 20 °C

3.1: 90 percent / silver trifluoroacetate; Br₂ / CHCl₃ / 1 h / 10 - 15 °C

4.1: 94 percent / pyridinium p-toluenesulfonate / CH₂Cl₂ / 2 h

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

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

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

6.2: dimethylformamide / 0.25 h / -5 °C

7.1: 76 percent / pyridinium p-toluenesulfonate / methanol / 2 h / 20 °C

8.1: 30 percent / benzene / 48 h / 5 °C / UV-irradiation

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

9.2: 98 percent / tetrahydrofuran / 24 h / 20 °C

10.1: 85 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.33 h / -5 °C

11.1: 83 percent / Dess-Martin periodinane / CH₂Cl₂ / 4 h

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

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

13.2: 47 mg / tetrabutylammonium iodide / dimethylformamide / 1 h / -10 °C

14.1: NaBH₄ / ethanol / 2 h

15.1: 81 mg / aq. H₂O₂ / ethanol / Heating

16.1: 89 percent / pyridine; acetone; H₂O / OsO₄ / 2-methyl-propan-2-ol; tetrahydrofuran / 4 h

With pyridine; sodium tetrahydroborate; n-butyllithium; tetrabutyl ammonium fluoride; water; dihydrogen peroxide; bromine; silver trifluoroacetate; pyridinium p-toluenesulfonate; sodium hydride; potassium carbonate; Dess-Martin periodane; 3-chloro-benzenecarboperoxoic acid; acetone; copper(II) oxide; osmium(VIII) oxide; In tetrahydrofuran; methanol; ethanol; dichloromethane; chloroform; N,N-dimethyl-formamide; tert-butyl alcohol; pentane; benzene; 1.1: acetalization / 2.1: Rearrangement / 2.2: Hydrolysis / 3.1: Bromination / 4.1: Addition / 5.1: Metallation / 5.2: Addition / 6.1: Metallation / 6.2: Substitution / 7.1: deprotection / 8.1: Cyclization / 9.1: Metallation / 9.2: Methylation / 10.1: Hydrolysis / 11.1: Oxidation / 12.1: Reduction / 13.1: Metallation / 13.2: Alkylation / 14.1: Ring cleavage / 15.1: oxidative elimination / 16.1: dihydroxylation;
DOI:10.1021/ja000930i