(1S,2R,3R,4aR,6aS,7R,8R,10aR,10bR,12aR)-benzyl 3-acetoxy-2-((S)-2-(((benzyloxy)carbonyl)(methyl)amino)-2,3-dimethylbutoxy)-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)chrysene-7-carboxylate

Base Information

• Chemical Name: (1S,2R,3R,4aR,6aS,7R,8R,10aR,10bR,12aR)-benzyl 3-acetoxy-2-((S)-2-(((benzyloxy)carbonyl)(methyl)amino)-2,3-dimethylbutoxy)-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)chrysene-7-carboxylate
• CAS No.: 1370547-48-0
• Molecular Formula: C₅₄H₇₅NO₉
• Molecular Weight: 882.191
• Mol file: 1370547-48-0.mol

Synonyms:

Chemical Property of (1S,2R,3R,4aR,6aS,7R,8R,10aR,10bR,12aR)-benzyl 3-acetoxy-2-((S)-2-(((benzyloxy)carbonyl)(methyl)amino)-2,3-dimethylbutoxy)-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)chrysene-7-carboxylate

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)-benzyl 3-acetoxy-2-((S)-2-(((benzyloxy)carbonyl)(methyl)amino)-2,3-dimethylbutoxy)-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)chrysene-7-carboxylate

There total 9 articles about (1S,2R,3R,4aR,6aS,7R,8R,10aR,10bR,12aR)-benzyl 3-acetoxy-2-((S)-2-(((benzyloxy)carbonyl)(methyl)amino)-2,3-dimethylbutoxy)-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)chrysene-7-carboxylate 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: 17.0%

(1S,2R,3R,4aR,6aS,7R,8R,10aR,10bR,12aR)-benzyl 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-carboxylate (1370547-47-9) → (1S,2R,3R,4aR,6aS,7R,8R,10aR,10bR,12aR)-benzyl 3-acetoxy-2-((S)-2-(((benzyloxy)carbonyl)(methyl)amino)-2,3-dimethylbutoxy)-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)chrysene-7-carboxylate (1370547-48-0)

Guidance literature:

With tert.-butylhydroperoxide; potassium carbonate; In acetonitrile; propiononitrile; at -30 ℃; for 288h;

DOI:10.1021/jo300046v

Reference yield:

C38H60O11 (388094-93-7) → (1S,2R,3R,4aR,6aS,7R,8R,10aR,10bR,12aR)-benzyl 3-acetoxy-2-((S)-2-(((benzyloxy)carbonyl)(methyl)amino)-2,3-dimethylbutoxy)-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)chrysene-7-carboxylate (1370547-48-0)

Guidance literature:

Multi-step reaction with 6 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: potassium carbonate / N,N-dimethyl-formamide / 0.5 h / 25 - 78 °C

6: tert.-butylhydroperoxide; ; potassium carbonate / acetonitrile; propiononitrile / 288 h / -30 °C

With tert.-butylhydroperoxide; sulfuric acid; potassium 2-methylbutan-2-olate; potassium carbonate; toluene-4-sulfonic acid; acetic acid; In N,N-dimethyl acetamide; Isopropyl acetate; N,N-dimethyl-formamide; toluene; acetonitrile; propiononitrile;

DOI:10.1021/jo300046v

Reference yield:

(1S,2R,3R,4aR,6aS,7R,8R,10aR,10bR,12aR)-2-hydroxy-3-methoxy-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-tetradeca-hydro-1H-1,4a-(methanooxymethano)chrysene-7-carboxylic acid (1140751-11-6) → (1S,2R,3R,4aR,6aS,7R,8R,10aR,10bR,12aR)-benzyl 3-acetoxy-2-((S)-2-(((benzyloxy)carbonyl)(methyl)amino)-2,3-dimethylbutoxy)-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)chrysene-7-carboxylate (1370547-48-0)

Guidance literature:

Multi-step reaction with 5 steps

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

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

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

4: potassium carbonate / N,N-dimethyl-formamide / 0.5 h / 25 - 78 °C

5: tert.-butylhydroperoxide; ; potassium carbonate / acetonitrile; propiononitrile / 288 h / -30 °C

With tert.-butylhydroperoxide; potassium 2-methylbutan-2-olate; potassium carbonate; toluene-4-sulfonic acid; acetic acid; In N,N-dimethyl acetamide; Isopropyl acetate; N,N-dimethyl-formamide; toluene; acetonitrile; propiononitrile;

DOI:10.1021/jo300046v

upstream raw materials:

(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

benzyl chloroformate

(1S,2R,3R,4aR,6aS,7R,8R,10aR,10bR,12aR)-benzyl 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-carboxylate

C₃₈H₆₀O₁₁