6,12-dihydroxy-4-(4-methoxy-benzyl)-2,2-dimethyl-3b,4,12,12a-tetrahydro-3aH-1,3,7,9-tetraoxa-4-aza-dicyclopenta[a,h]phenanthren-5-one

Base Information

• Chemical Name: 6,12-dihydroxy-4-(4-methoxy-benzyl)-2,2-dimethyl-3b,4,12,12a-tetrahydro-3aH-1,3,7,9-tetraoxa-4-aza-dicyclopenta[a,h]phenanthren-5-one
• CAS No.: 288395-87-9
• Molecular Formula: C₂₅H₂₅NO₈
• Molecular Weight: 467.475

Synonyms:6,12-dihydroxy-4-(4-methoxy-benzyl)-2,2-dimethyl-3b,4,12,12a-tetrahydro-3aH-1,3,7,9-tetraoxa-4-aza-dicyclopenta[a,h]phenanthren-5-one

Chemical Property of 6,12-dihydroxy-4-(4-methoxy-benzyl)-2,2-dimethyl-3b,4,12,12a-tetrahydro-3aH-1,3,7,9-tetraoxa-4-aza-dicyclopenta[a,h]phenanthren-5-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 6,12-dihydroxy-4-(4-methoxy-benzyl)-2,2-dimethyl-3b,4,12,12a-tetrahydro-3aH-1,3,7,9-tetraoxa-4-aza-dicyclopenta[a,h]phenanthren-5-one

There total 25 articles about 6,12-dihydroxy-4-(4-methoxy-benzyl)-2,2-dimethyl-3b,4,12,12a-tetrahydro-3aH-1,3,7,9-tetraoxa-4-aza-dicyclopenta[a,h]phenanthren-5-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:

Acetic acid (3aS,3bR,12S,12aR)-6-acetoxy-4-(4-methoxy-benzyl)-2,2-dimethyl-5-oxo-3a,3b,4,5,12,12a-hexahydro-1,3,7,9-tetraoxa-4-aza-dicyclopenta[a,h]phenanthren-12-yl ester (200182-37-2) → 6,12-dihydroxy-4-(4-methoxy-benzyl)-2,2-dimethyl-3b,4,12,12a-tetrahydro-3aH-1,3,7,9-tetraoxa-4-aza-dicyclopenta[a,h]phenanthren-5-one (288395-87-9)

Guidance literature:

With potassium carbonate; In methanol;

DOI:10.1021/ja972950z

Reference yield:

2,4-Cyclohexadien-1-carbonsaeure-methylester (54162-19-5) → 6,12-dihydroxy-4-(4-methoxy-benzyl)-2,2-dimethyl-3b,4,12,12a-tetrahydro-3aH-1,3,7,9-tetraoxa-4-aza-dicyclopenta[a,h]phenanthren-5-one (288395-87-9)

Guidance literature:

Multi-step reaction with 18 steps

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

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

1.3: 42 percent / NaOMe / methanol / 0.5 h / -5 °C

2.1: 99 percent / Et₃N; 4-dimethylaminopyridine / CH₂Cl₂ / 0 - 20 °C

3.1: 80 percent Turnov_. / cholesterol esterase; aq. NaOH / 36 h / 5 °C / pH 7.7

4.1: 98 percent / imidazole / dimethylformamide / 0.67 h / 20 °C

5.1: 81 percent Turnov_. / LiOH*H₂O / methanol / 48 h / -5 °C

6.1: diphenylphosphorazidate; Et₃N / benzene / 1 h

6.2: toluene / 1 h / 110 °C

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

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

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

8.2: dimethylformamide / 0.25 h / -5 °C

9.1: 76 percent / pyridinium p-toluenesulfonate / methanol / 2 h / 20 °C

10.1: 30 percent / benzene / 48 h / 5 °C / UV-irradiation

11.1: NaBH₄ / ethanol / 16 h / 20 °C

12.1: 12.9 mg / aq. H₂O₂ / tetrahydrofuran; ethanol / 22 h / 20 °C

13.1: NaH / tetrahydrofuran / 0.33 h / 20 °C

13.2: 94 percent / tetrahydrofuran / 20 h / 20 °C

14.1: pyridine; trimethylamine-N-oxide dihydrate; H₂O / OsO₄; acetone / 2-methyl-propan-2-ol; tetrahydrofuran / 15 h / 20 °C

15.1: 19.2 mg / p-TsOH / 2 h / 20 °C

16.1: tetrabutylammonium fluoride / tetrahydrofuran / 0.83 h / 0 °C

17.1: 7.1 mg / Burgess reagent / benzene / 16 h / Heating

18.1: 3.3 mg / K₂CO₃; H₂O / methanol / 20 °C

With pyridine; 1H-imidazole; dmap; lithium hydroxide; sodium hydroxide; sodium tetrahydroborate; n-butyllithium; cholesterol esterase; Burgess Reagent; trimethylamine-N-oxide; diphenyl phosphoryl azide; tetrabutyl ammonium fluoride; water; dihydrogen peroxide; oxygen; pyridinium p-toluenesulfonate; rose bengal; sodium hydride; potassium carbonate; triethylamine; osmium(VIII) oxide; toluene-4-sulfonic acid; acetone; In tetrahydrofuran; methanol; ethanol; dichloromethane; N,N-dimethyl-formamide; acetone; tert-butyl alcohol; pentane; benzene; 1.1: Oxidation / 1.2: Epoxidation / 1.3: Ring cleavage / 2.1: Acylation / 3.1: Hydrolysis / 4.1: silylation / 5.1: Hydrolysis / 6.1: azidation / 6.2: Rearrangement / 7.1: Metallation / 7.2: Addition / 8.1: Metallation / 8.2: Substitution / 9.1: deprotection / 10.1: Cyclization / 11.1: Ring cleavage / 12.1: oxidative elimination / 13.1: Metallation / 13.2: Acetylation / 14.1: dihydroxylation / 15.1: Addition / 16.1: Hydrolysis / 17.1: Dehydration / 18.1: Deacetylation;

DOI:10.1021/ja000930i

Reference yield:

bromo-5 hydroxy-4 benzodioxole-1,3 (82299-36-3) → 6,12-dihydroxy-4-(4-methoxy-benzyl)-2,2-dimethyl-3b,4,12,12a-tetrahydro-3aH-1,3,7,9-tetraoxa-4-aza-dicyclopenta[a,h]phenanthren-5-one (288395-87-9)

Guidance literature:

Multi-step reaction with 13 steps

1.1: 94 percent / pyridinium p-toluenesulfonate / CH₂Cl₂ / 2 h

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

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

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

3.2: dimethylformamide / 0.25 h / -5 °C

4.1: 76 percent / pyridinium p-toluenesulfonate / methanol / 2 h / 20 °C

5.1: 30 percent / benzene / 48 h / 5 °C / UV-irradiation

6.1: NaBH₄ / ethanol / 16 h / 20 °C

7.1: 12.9 mg / aq. H₂O₂ / tetrahydrofuran; ethanol / 22 h / 20 °C

8.1: NaH / tetrahydrofuran / 0.33 h / 20 °C

8.2: 94 percent / tetrahydrofuran / 20 h / 20 °C

9.1: pyridine; trimethylamine-N-oxide dihydrate; H₂O / OsO₄; acetone / 2-methyl-propan-2-ol; tetrahydrofuran / 15 h / 20 °C

10.1: 19.2 mg / p-TsOH / 2 h / 20 °C

11.1: tetrabutylammonium fluoride / tetrahydrofuran / 0.83 h / 0 °C

12.1: 7.1 mg / Burgess reagent / benzene / 16 h / Heating

13.1: 3.3 mg / K₂CO₃; H₂O / methanol / 20 °C

With pyridine; sodium tetrahydroborate; n-butyllithium; Burgess Reagent; trimethylamine-N-oxide; tetrabutyl ammonium fluoride; water; dihydrogen peroxide; pyridinium p-toluenesulfonate; sodium hydride; potassium carbonate; osmium(VIII) oxide; toluene-4-sulfonic acid; acetone; In tetrahydrofuran; methanol; ethanol; dichloromethane; N,N-dimethyl-formamide; tert-butyl alcohol; pentane; benzene; 1.1: Addition / 2.1: Metallation / 2.2: Addition / 3.1: Metallation / 3.2: Substitution / 4.1: deprotection / 5.1: Cyclization / 6.1: Ring cleavage / 7.1: oxidative elimination / 8.1: Metallation / 8.2: Acetylation / 9.1: dihydroxylation / 10.1: Addition / 11.1: Hydrolysis / 12.1: Dehydration / 13.1: Deacetylation;

DOI:10.1021/ja000930i

upstream raw materials:

Acetic acid (3aS,3bR,12S,12aR)-6-acetoxy-4-(4-methoxy-benzyl)-2,2-dimethyl-5-oxo-3a,3b,4,5,12,12a-hexahydro-1,3,7,9-tetraoxa-4-aza-dicyclopenta[a,h]phenanthren-12-yl ester

2,3-dihydroxybenzaldehyde

methyl cyclohex-3-ene-1-carboxylate

2,4-Cyclohexadien-1-carbonsaeure-methylester

Downstream raw materials:

narciclasine

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