(1S,2R,3R,4aR,6aS,7R,8R,10aR,10bR,12aR)-3-acetoxy-2-((S)-2-(((benzyloxy)carbonyl)(methyl)amino)-2,3-dimethylbutoxy)-1,6a,8,10a-tetramethyl-8-((R)-3-methylbutan-2-yl)-2,3,4,6,6a,7,8,9,10,10a,10b,11,12,12a-tetradecahydro-1H-1,4a-(methanooxymethano)chrysene-7-carboxylic acid

Base Information

• Chemical Name: (1S,2R,3R,4aR,6aS,7R,8R,10aR,10bR,12aR)-3-acetoxy-2-((S)-2-(((benzyloxy)carbonyl)(methyl)amino)-2,3-dimethylbutoxy)-1,6a,8,10a-tetramethyl-8-((R)-3-methylbutan-2-yl)-2,3,4,6,6a,7,8,9,10,10a,10b,11,12,12a-tetradecahydro-1H-1,4a-(methanooxymethano)chrysene-7-carboxylic acid
• CAS No.: 1370547-50-4
• Molecular Formula: C₄₇H₇₁NO₈
• Molecular Weight: 778.083
• Mol file: 1370547-50-4.mol

Synonyms:

Chemical Property of (1S,2R,3R,4aR,6aS,7R,8R,10aR,10bR,12aR)-3-acetoxy-2-((S)-2-(((benzyloxy)carbonyl)(methyl)amino)-2,3-dimethylbutoxy)-1,6a,8,10a-tetramethyl-8-((R)-3-methylbutan-2-yl)-2,3,4,6,6a,7,8,9,10,10a,10b,11,12,12a-tetradecahydro-1H-1,4a-(methanooxymethano)chrysene-7-carboxylic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,2R,3R,4aR,6aS,7R,8R,10aR,10bR,12aR)-3-acetoxy-2-((S)-2-(((benzyloxy)carbonyl)(methyl)amino)-2,3-dimethylbutoxy)-1,6a,8,10a-tetramethyl-8-((R)-3-methylbutan-2-yl)-2,3,4,6,6a,7,8,9,10,10a,10b,11,12,12a-tetradecahydro-1H-1,4a-(methanooxymethano)chrysene-7-carboxylic acid

There total 11 articles about (1S,2R,3R,4aR,6aS,7R,8R,10aR,10bR,12aR)-3-acetoxy-2-((S)-2-(((benzyloxy)carbonyl)(methyl)amino)-2,3-dimethylbutoxy)-1,6a,8,10a-tetramethyl-8-((R)-3-methylbutan-2-yl)-2,3,4,6,6a,7,8,9,10,10a,10b,11,12,12a-tetradecahydro-1H-1,4a-(methanooxymethano)chrysene-7-carboxylic acid 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:

(S)-2-ethoxycarbonylamino-2,3-dimethylbutyric acid (952577-51-4) → (1S,2R,3R,4aR,6aS,7R,8R,10aR,10bR,12aR)-3-acetoxy-2-((S)-2-(((benzyloxy)carbonyl)(methyl)amino)-2,3-dimethylbutoxy)-1,6a,8,10a-tetramethyl-8-((R)-3-methylbutan-2-yl)-2,3,4,6,6a,7,8,9,10,10a,10b,11,12,12a-tetradecahydro-1H-1,4a-(methanooxymethano)chrysene-7-carboxylic acid (1370547-50-4)

Guidance literature:

Multi-step reaction with 8 steps

1: lithium aluminium tetrahydride / tetrahydrofuran; 2-methyltetrahydrofuran / 60 °C / Large scale reaction

2: thionyl chloride; N-ethyl-N,N-diisopropylamine / dichloromethane / -17 - -3 °C / Large scale reaction

3: sodium periodate; rhodium(III) chloride hydrate / acetonitrile / 20 °C / Large scale reaction

4: potassium 2-methylbutan-2-olate / N,N-dimethyl acetamide; toluene / 24.5 h / 20 - 25 °C / Large scale reaction

5: toluene-4-sulfonic acid; acetic acid / Isopropyl acetate / 3.5 h / 20 - 60 °C / Large scale reaction

6: palladium 10% on activated carbon; formic acid; triethylamine / tetrahydrofuran / 0.5 h / 50 °C / Large scale reaction

7: potassium carbonate / tetrahydrofuran; toluene / 3 h / 20 °C

8: sodium hydroxide / 6 h / 20 °C / Large scale reaction

With sodium periodate; lithium aluminium tetrahydride; formic acid; thionyl chloride; rhodium(III) chloride hydrate; palladium 10% on activated carbon; potassium 2-methylbutan-2-olate; potassium carbonate; toluene-4-sulfonic acid; acetic acid; triethylamine; N-ethyl-N,N-diisopropylamine; sodium hydroxide; In tetrahydrofuran; 2-methyltetrahydrofuran; dichloromethane; N,N-dimethyl acetamide; Isopropyl acetate; toluene; acetonitrile;

DOI:10.1021/jo300046v

Reference yield:

(1S,2R,3R,4aR,6aS,7R,8R,10aR,10bR,12aR)-3-acetoxy-2-((S)-2,3-dimethyl-2-(methylamino)butoxy)-1,6a,8,10a-tetramethyl-8-((R)-3-methylbutan-2-yl)-2,3,4,6,6a,7,8,9,10,10a,10b,-11,12,12a-tetradecahydro-1H-1,4a-(methanooxymethano)-chrysene-7-carboxylic acid (1370547-49-1) → (1S,2R,3R,4aR,6aS,7R,8R,10aR,10bR,12aR)-3-acetoxy-2-((S)-2-(((benzyloxy)carbonyl)(methyl)amino)-2,3-dimethylbutoxy)-1,6a,8,10a-tetramethyl-8-((R)-3-methylbutan-2-yl)-2,3,4,6,6a,7,8,9,10,10a,10b,11,12,12a-tetradecahydro-1H-1,4a-(methanooxymethano)chrysene-7-carboxylic acid (1370547-50-4)

Guidance literature:

Multi-step reaction with 2 steps

1: potassium carbonate / tetrahydrofuran; toluene / 3 h / 20 °C

2: sodium hydroxide / 6 h / 20 °C / Large scale reaction

With potassium carbonate; sodium hydroxide; In tetrahydrofuran; toluene;

DOI:10.1021/jo300046v

Reference yield:

C38H60O11 (388094-93-7) → (1S,2R,3R,4aR,6aS,7R,8R,10aR,10bR,12aR)-3-acetoxy-2-((S)-2-(((benzyloxy)carbonyl)(methyl)amino)-2,3-dimethylbutoxy)-1,6a,8,10a-tetramethyl-8-((R)-3-methylbutan-2-yl)-2,3,4,6,6a,7,8,9,10,10a,10b,11,12,12a-tetradecahydro-1H-1,4a-(methanooxymethano)chrysene-7-carboxylic acid (1370547-50-4)

Guidance literature:

Multi-step reaction with 7 steps

1: sulfuric acid / 14 h / Reflux; Large scale reaction

2: potassium carbonate / N,N-dimethyl-formamide / 0.5 h / 25 - 78 °C / Large scale reaction

3: potassium 2-methylbutan-2-olate / N,N-dimethyl acetamide; toluene / 24.5 h / 20 - 25 °C / Large scale reaction

4: toluene-4-sulfonic acid; acetic acid / Isopropyl acetate / 3.5 h / 20 - 60 °C / Large scale reaction

5: palladium 10% on activated carbon; formic acid; triethylamine / tetrahydrofuran / 0.5 h / 50 °C / Large scale reaction

6: potassium carbonate / tetrahydrofuran; toluene / 3 h / 20 °C

7: sodium hydroxide / 6 h / 20 °C / Large scale reaction

With formic acid; sulfuric acid; palladium 10% on activated carbon; potassium 2-methylbutan-2-olate; potassium carbonate; toluene-4-sulfonic acid; acetic acid; triethylamine; sodium hydroxide; In tetrahydrofuran; N,N-dimethyl acetamide; Isopropyl acetate; N,N-dimethyl-formamide; toluene;

DOI:10.1021/jo300046v

upstream raw materials:

(S)-2-ethoxycarbonylamino-2,3-dimethylbutyric acid

(1S,2R,3R,4aR,6aS,7R,8R,10aR,10bR,12aR)-benzyl 3-acetoxy-2-((S)-2,3-dimethyl-2-(methylamino)butoxy)-1,6a,8,10a-tetramethyl-8-((R)-3-methylbutan-2-yl)-2,3,4,6,6a,7,8,9,10,10a,10b,11,12,12a-tetradecahydro-1H-1,4a-(methanooxymethano)chrysene-7-carboxylate

(1S,2R,3R,4aR,6aS,7R,8R,10aR,10bR,12aR)-3-acetoxy-2-((S)-2,3-dimethyl-2-(methylamino)butoxy)-1,6a,8,10a-tetramethyl-8-((R)-3-methylbutan-2-yl)-2,3,4,6,6a,7,8,9,10,10a,10b,-11,12,12a-tetradecahydro-1H-1,4a-(methanooxymethano)-chrysene-7-carboxylic acid

C₃₈H₆₀O₁₁

Downstream raw materials:

C₄₇H₆₉NO₇

(1S,2R,3R,4aR,6aS,7R,8R,10aR,10bR,12aR)-2-((S)-2-(((benzyloxy)carbonyl)(methyl)amino)-2,3-dimethylbutoxy)-7-carbamoyl-1,6a,8,10a-tetramethyl-8-((R)-3-methylbutan-2-yl)-2,3,4,6,6a,7,8,9,10,10a,10b,11,12,12a-tetradecahydro-1H-1,4a-(methanooxymethano)chrysen-3-yl acetate

(1S,2R,3R,4aR,6aS,7R,8R,10aR,10bR,12aR)-2-((S)-2-(((benzyloxy)carbonyl)(methyl)amino)-2,3-dimethylbutoxy)-7-carbamoyl-1,6a,8,10a-tetramethyl-8-((R)-3-methylbutan-2-yl)-6-oxo-2,3,4,6,6a,7,8,9,10,10a,10b,11,12,12a-tetradecahydro-1H-1,4a-(methanooxymethano)chrysen-3-yl acetate

(1S,2R,3R,4aR,6R,6aS,7R,8R,10aR,10bR,12aR)-2-((S)-2-(((benzyloxy)carbonyl)(methyl)amino)-2,3-dimethylbutoxy)-6-(tert-butylperoxy)-7-carbamoyl-1,6a,8,10a-tetramethyl-8-((R)-3-methylbutan-2-yl)-2,3,4,6,6a,7,8,9,10,10a,10b,11,12,12a-tetradecahydro-1H-1,4a-(methanooxymethano)chrysen-3-yl acetate