Acetic acid (3aS,3bR,10bR,11S,12S,12aS)-6-acetoxy-11-hydroxy-4-(4-methoxy-benzyl)-2,2-dimethyl-5-oxo-3a,3b,4,5,10b,11,12,12a-octahydro-1,3,7,9-tetraoxa-4-aza-dicyclopenta[a,h]phenanthren-12-yl ester

Base Information

• Chemical Name: Acetic acid (3aS,3bR,10bR,11S,12S,12aS)-6-acetoxy-11-hydroxy-4-(4-methoxy-benzyl)-2,2-dimethyl-5-oxo-3a,3b,4,5,10b,11,12,12a-octahydro-1,3,7,9-tetraoxa-4-aza-dicyclopenta[a,h]phenanthren-12-yl ester
• CAS No.: 288395-86-8
• Molecular Formula: C₂₉H₃₁NO₁₁
• Molecular Weight: 569.565

Synonyms:Acetic acid (3aS,3bR,10bR,11S,12S,12aS)-6-acetoxy-11-hydroxy-4-(4-methoxy-benzyl)-2,2-dimethyl-5-oxo-3a,3b,4,5,10b,11,12,12a-octahydro-1,3,7,9-tetraoxa-4-aza-dicyclopenta[a,h]phenanthren-12-yl ester

Chemical Property of Acetic acid (3aS,3bR,10bR,11S,12S,12aS)-6-acetoxy-11-hydroxy-4-(4-methoxy-benzyl)-2,2-dimethyl-5-oxo-3a,3b,4,5,10b,11,12,12a-octahydro-1,3,7,9-tetraoxa-4-aza-dicyclopenta[a,h]phenanthren-12-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Acetic acid (3aS,3bR,10bR,11S,12S,12aS)-6-acetoxy-11-hydroxy-4-(4-methoxy-benzyl)-2,2-dimethyl-5-oxo-3a,3b,4,5,10b,11,12,12a-octahydro-1,3,7,9-tetraoxa-4-aza-dicyclopenta[a,h]phenanthren-12-yl ester

There total 22 articles about Acetic acid (3aS,3bR,10bR,11S,12S,12aS)-6-acetoxy-11-hydroxy-4-(4-methoxy-benzyl)-2,2-dimethyl-5-oxo-3a,3b,4,5,10b,11,12,12a-octahydro-1,3,7,9-tetraoxa-4-aza-dicyclopenta[a,h]phenanthren-12-yl ester 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:

2,4-Cyclohexadien-1-carbonsaeure-methylester (54162-19-5) → Acetic acid (3aS,3bR,10bR,11S,12S,12aS)-6-acetoxy-11-hydroxy-4-(4-methoxy-benzyl)-2,2-dimethyl-5-oxo-3a,3b,4,5,10b,11,12,12a-octahydro-1,3,7,9-tetraoxa-4-aza-dicyclopenta[a,h]phenanthren-12-yl ester (288395-86-8)

Guidance literature:

Multi-step reaction with 16 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

With pyridine; 1H-imidazole; dmap; lithium hydroxide; sodium hydroxide; sodium tetrahydroborate; n-butyllithium; cholesterol esterase; trimethylamine-N-oxide; diphenyl phosphoryl azide; tetrabutyl ammonium fluoride; water; dihydrogen peroxide; oxygen; pyridinium p-toluenesulfonate; rose bengal; sodium hydride; 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;

DOI:10.1021/ja000930i

Reference yield:

methyl 2-hydroxy-7-oxabicyclo[4.1.0]hept-3-ene-4-carboxylate (200182-30-5) → Acetic acid (3aS,3bR,10bR,11S,12S,12aS)-6-acetoxy-11-hydroxy-4-(4-methoxy-benzyl)-2,2-dimethyl-5-oxo-3a,3b,4,5,10b,11,12,12a-octahydro-1,3,7,9-tetraoxa-4-aza-dicyclopenta[a,h]phenanthren-12-yl ester (288395-86-8)

Guidance literature:

Multi-step reaction with 15 steps

1.1: 99 percent / Et₃N; 4-dimethylaminopyridine / CH₂Cl₂ / 0 - 20 °C

2.1: 80 percent Turnov_. / cholesterol esterase; aq. NaOH / 36 h / 5 °C / pH 7.7

3.1: 98 percent / imidazole / dimethylformamide / 0.67 h / 20 °C

4.1: 81 percent Turnov_. / LiOH*H₂O / methanol / 48 h / -5 °C

5.1: diphenylphosphorazidate; Et₃N / benzene / 1 h

5.2: toluene / 1 h / 110 °C

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

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

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

7.2: dimethylformamide / 0.25 h / -5 °C

8.1: 76 percent / pyridinium p-toluenesulfonate / methanol / 2 h / 20 °C

9.1: 30 percent / benzene / 48 h / 5 °C / UV-irradiation

10.1: NaBH₄ / ethanol / 16 h / 20 °C

11.1: 12.9 mg / aq. H₂O₂ / tetrahydrofuran; ethanol / 22 h / 20 °C

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

12.2: 94 percent / tetrahydrofuran / 20 h / 20 °C

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

14.1: 19.2 mg / p-TsOH / 2 h / 20 °C

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

With pyridine; 1H-imidazole; dmap; lithium hydroxide; sodium hydroxide; sodium tetrahydroborate; n-butyllithium; cholesterol esterase; trimethylamine-N-oxide; diphenyl phosphoryl azide; tetrabutyl ammonium fluoride; water; dihydrogen peroxide; pyridinium p-toluenesulfonate; sodium hydride; triethylamine; osmium(VIII) oxide; toluene-4-sulfonic acid; acetone; In tetrahydrofuran; methanol; ethanol; dichloromethane; N,N-dimethyl-formamide; tert-butyl alcohol; pentane; benzene; 1.1: Acylation / 2.1: Hydrolysis / 3.1: silylation / 4.1: Hydrolysis / 5.1: azidation / 5.2: Rearrangement / 6.1: Metallation / 6.2: Addition / 7.1: Metallation / 7.2: Substitution / 8.1: deprotection / 9.1: Cyclization / 10.1: Ring cleavage / 11.1: oxidative elimination / 12.1: Metallation / 12.2: Acetylation / 13.1: dihydroxylation / 14.1: Addition / 15.1: Hydrolysis;

DOI:10.1021/ja000930i

Reference yield:

bromo-5 hydroxy-4 benzodioxole-1,3 (82299-36-3) → Acetic acid (3aS,3bR,10bR,11S,12S,12aS)-6-acetoxy-11-hydroxy-4-(4-methoxy-benzyl)-2,2-dimethyl-5-oxo-3a,3b,4,5,10b,11,12,12a-octahydro-1,3,7,9-tetraoxa-4-aza-dicyclopenta[a,h]phenanthren-12-yl ester (288395-86-8)

Guidance literature:

Multi-step reaction with 11 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

With pyridine; sodium tetrahydroborate; n-butyllithium; trimethylamine-N-oxide; tetrabutyl ammonium fluoride; water; dihydrogen peroxide; pyridinium p-toluenesulfonate; sodium hydride; 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;

DOI:10.1021/ja000930i

upstream raw materials:

2,3-dihydroxybenzaldehyde

methyl cyclohex-3-ene-1-carboxylate

2,4-Cyclohexadien-1-carbonsaeure-methylester

2H-benzo[d][1,3]dioxolan-4-ol

Downstream 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

narciclasine

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

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