2-(4-methoxy-phenyl)-4-phenyl-oxazolidine-3,5-dicarboxylic acid 5-(4-acetoxy-2-benzoyloxy-1-hydroxy-8,12,15,15-tetramethyl-9-oxo-7,10-bis-triethylsilanyloxy-tricyclo[9.3.1.0^3,8]pentadec-11-en-13-yl) ester 3-tert-butyl ester

Base Information

• Chemical Name: 2-(4-methoxy-phenyl)-4-phenyl-oxazolidine-3,5-dicarboxylic acid 5-(4-acetoxy-2-benzoyloxy-1-hydroxy-8,12,15,15-tetramethyl-9-oxo-7,10-bis-triethylsilanyloxy-tricyclo[9.3.1.0^3,8]pentadec-11-en-13-yl) ester 3-tert-butyl ester
• CAS No.: 646502-75-2
• Molecular Formula: C₆₂H₈₇NO₁₄Si₂
• Molecular Weight: 1126.54

Synonyms:2-(4-methoxy-phenyl)-4-phenyl-oxazolidine-3,5-dicarboxylic acid 5-(4-acetoxy-2-benzoyloxy-1-hydroxy-8,12,15,15-tetramethyl-9-oxo-7,10-bis-triethylsilanyloxy-tricyclo[9.3.1.0^3,8]pentadec-11-en-13-yl) ester 3-tert-butyl ester

Chemical Property of 2-(4-methoxy-phenyl)-4-phenyl-oxazolidine-3,5-dicarboxylic acid 5-(4-acetoxy-2-benzoyloxy-1-hydroxy-8,12,15,15-tetramethyl-9-oxo-7,10-bis-triethylsilanyloxy-tricyclo[9.3.1.0^3,8]pentadec-11-en-13-yl) ester 3-tert-butyl ester

Chemical Property:

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Technology Process of 2-(4-methoxy-phenyl)-4-phenyl-oxazolidine-3,5-dicarboxylic acid 5-(4-acetoxy-2-benzoyloxy-1-hydroxy-8,12,15,15-tetramethyl-9-oxo-7,10-bis-triethylsilanyloxy-tricyclo[9.3.1.0^3,8]pentadec-11-en-13-yl) ester 3-tert-butyl ester

There total 7 articles about 2-(4-methoxy-phenyl)-4-phenyl-oxazolidine-3,5-dicarboxylic acid 5-(4-acetoxy-2-benzoyloxy-1-hydroxy-8,12,15,15-tetramethyl-9-oxo-7,10-bis-triethylsilanyloxy-tricyclo[9.3.1.0^3,8]pentadec-11-en-13-yl) ester 3-tert-butyl 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: 93.0%

(2R,4S,5R)-(2R,4S,5R)-3-tert-butoxycarbonyl-2-(4-methoxyphenyl)-4-phenyl-1,3-oxazolidine-5-carboxylic acid (155396-69-3) + Benzoic acid (1S,2S,3S,4S,7S,8S,10R,13S)-4-acetoxy-1,13-dihydroxy-8,12,15,15-tetramethyl-9-oxo-7,10-bis-triethylsilanyloxy-tricyclo[9.3.1.03,8]pentadec-11-en-2-yl ester (646502-73-0) → 2-(4-methoxy-phenyl)-4-phenyl-oxazolidine-3,5-dicarboxylic acid 5-(4-acetoxy-2-benzoyloxy-1-hydroxy-8,12,15,15-tetramethyl-9-oxo-7,10-bis-triethylsilanyloxy-tricyclo[9.3.1.03,8]pentadec-11-en-13-yl) ester 3-tert-butyl ester (646502-75-2)

Guidance literature:

With dmap; dicyclohexyl-carbodiimide; In toluene; at 20 ℃; for 0.333333h;

DOI:10.1021/ol036043c

Reference yield:

2-debenzoyl-4-deacetyl-5α-bromo-7,10-di(triethylsilyl)-20-hydroxy-13-oxo-D-seco-10-deacetylbaccatin III 1,2 carbonate (285118-31-2) → 2-(4-methoxy-phenyl)-4-phenyl-oxazolidine-3,5-dicarboxylic acid 5-(4-acetoxy-2-benzoyloxy-1-hydroxy-8,12,15,15-tetramethyl-9-oxo-7,10-bis-triethylsilanyloxy-tricyclo[9.3.1.03,8]pentadec-11-en-13-yl) ester 3-tert-butyl ester (646502-75-2)

Guidance literature:

Multi-step reaction with 7 steps

1: 98.8 percent / Pb(OAc)4 / acetonitrile / 1 h / 0 °C

2: 63.2 percent / (R)-2-methyl-CBS-oxazaborolidine; BH₃*Me₂S / tetrahydrofuran; toluene; CH₂Cl₂ / 0.17 h / -20 °C

3: 86 percent / pyridine; 4-(dimethylamino)pyridine / CH₂Cl₂ / 5 h / 40 °C

4: 88 percent / H₂; pyridine / Pd/C / methanol / 4 h

5: 67 percent / tetrahydrofuran; cyclohexane / 0.33 h / -78 °C

6: 30 percent / NaBH₄ / methanol; tetrahydrofuran / 20 °C

7: 93 percent / 4-(dimethylamino)pyridine; dicyclohexylcarbodiimide / toluene / 0.33 h / 20 °C

With pyridine; lead(IV) acetate; dmap; sodium tetrahydroborate; dimethylsulfide borane complex; hydrogen; dicyclohexyl-carbodiimide; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; cyclohexane; toluene; acetonitrile;

DOI:10.1021/ol036043c

Reference yield:

C32H51BrO8Si2 (646502-66-1) → 2-(4-methoxy-phenyl)-4-phenyl-oxazolidine-3,5-dicarboxylic acid 5-(4-acetoxy-2-benzoyloxy-1-hydroxy-8,12,15,15-tetramethyl-9-oxo-7,10-bis-triethylsilanyloxy-tricyclo[9.3.1.03,8]pentadec-11-en-13-yl) ester 3-tert-butyl ester (646502-75-2)

Guidance literature:

Multi-step reaction with 6 steps

1: 63.2 percent / (R)-2-methyl-CBS-oxazaborolidine; BH₃*Me₂S / tetrahydrofuran; toluene; CH₂Cl₂ / 0.17 h / -20 °C

2: 86 percent / pyridine; 4-(dimethylamino)pyridine / CH₂Cl₂ / 5 h / 40 °C

3: 88 percent / H₂; pyridine / Pd/C / methanol / 4 h

4: 67 percent / tetrahydrofuran; cyclohexane / 0.33 h / -78 °C

5: 30 percent / NaBH₄ / methanol; tetrahydrofuran / 20 °C

6: 93 percent / 4-(dimethylamino)pyridine; dicyclohexylcarbodiimide / toluene / 0.33 h / 20 °C

With pyridine; dmap; sodium tetrahydroborate; dimethylsulfide borane complex; hydrogen; dicyclohexyl-carbodiimide; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; cyclohexane; toluene;

DOI:10.1021/ol036043c

upstream raw materials:

(2R,4S,5R)-(2R,4S,5R)-3-tert-butoxycarbonyl-2-(4-methoxyphenyl)-4-phenyl-1,3-oxazolidine-5-carboxylic acid

Benzoic acid (1S,2S,3S,4S,7S,8S,10R,13S)-4-acetoxy-1,13-dihydroxy-8,12,15,15-tetramethyl-9-oxo-7,10-bis-triethylsilanyloxy-tricyclo[9.3.1.0^3,8]pentadec-11-en-2-yl ester

2-debenzoyl-4-deacetyl-5α-bromo-7,10-di(triethylsilyl)-20-hydroxy-13-oxo-D-seco-10-deacetylbaccatin III 1,2 carbonate

C₃₂H₅₁BrO₈Si₂

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