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

Base Information

• Chemical Name: 2-(4-methoxy-phenyl)-4-phenyl-oxazolidine-3,5-dicarboxylic acid 3-tert-butyl ester 5-(4,10-diacetoxy-2-benzoyloxy-1-hydroxy-4,8,12,15,15-pentamethyl-5,9-dioxo-7-triethylsilanyloxy-tricyclo[9.3.1.0^3,8]pentadec-11-en-13-yl) ester
• CAS No.: 892859-28-8
• Molecular Formula: C₅₉H₇₅NO₁₆Si
• Molecular Weight: 1082.33

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

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

Chemical Property:

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

There total 12 articles about 2-(4-methoxy-phenyl)-4-phenyl-oxazolidine-3,5-dicarboxylic acid 3-tert-butyl ester 5-(4,10-diacetoxy-2-benzoyloxy-1-hydroxy-4,8,12,15,15-pentamethyl-5,9-dioxo-7-triethylsilanyloxy-tricyclo[9.3.1.0^3,8]pentadec-11-en-13-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: 54.0%

Benzoic acid (1S,2S,3R,4R,7S,8S,10R,13S)-4,10-diacetoxy-1,13-dihydroxy-4,8,12,15,15-pentamethyl-5,9-dioxo-7-triethylsilanyloxy-tricyclo[9.3.1.03,8]pentadec-11-en-2-yl ester (892859-27-7) + (2R,4S,5R)-(2R,4S,5R)-3-tert-butoxycarbonyl-2-(4-methoxyphenyl)-4-phenyl-1,3-oxazolidine-5-carboxylic acid (155396-69-3) → 2-(4-methoxy-phenyl)-4-phenyl-oxazolidine-3,5-dicarboxylic acid 3-tert-butyl ester 5-(4,10-diacetoxy-2-benzoyloxy-1-hydroxy-4,8,12,15,15-pentamethyl-5,9-dioxo-7-triethylsilanyloxy-tricyclo[9.3.1.03,8]pentadec-11-en-13-yl) ester (892859-28-8)

Guidance literature:

With dmap; dicyclohexyl-carbodiimide; In toluene; at 70 ℃; for 10h;

DOI:10.1021/ol060531d

Reference yield:

C39H70O9Si3 (892859-19-7) → 2-(4-methoxy-phenyl)-4-phenyl-oxazolidine-3,5-dicarboxylic acid 3-tert-butyl ester 5-(4,10-diacetoxy-2-benzoyloxy-1-hydroxy-4,8,12,15,15-pentamethyl-5,9-dioxo-7-triethylsilanyloxy-tricyclo[9.3.1.03,8]pentadec-11-en-13-yl) ester (892859-28-8)

Guidance literature:

Multi-step reaction with 9 steps

1: 76 percent / tetrabutylammonium iodide; boron trifluoride etherate / tetrahydrofuran / 0.33 h / 20 °C

2: 85 percent / H₂; pyridine / Pd/C / methanol / 24 h

3: 86 percent / DMSO; trifluoroacetic anhydride; Et₃N / CH₂Cl₂ / 1 h / -60 - -40 °C

4: 68 percent / 4-DMAP / CH₂Cl₂ / 19 h / 20 °C

5: 88 percent / tetrahydrofuran; hexane / 0.5 h / -72 °C

6: 85 percent / hydrogen fluoride/pyridine; pyridine / tetrahydrofuran / 17 h / 20 °C

7: 58 percent / ZnCl₂ / tetrahydrofuran / 0.5 h / 20 °C

8: 20 percent / pyridine; DMAP / 5 h / 60 °C

9: 54 percent / DCC; DMAP / toluene / 10 h / 70 °C

With pyridine; dmap; boron trifluoride diethyl etherate; hydrogen fluoride; hydrogen; tetra-(n-butyl)ammonium iodide; dimethyl sulfoxide; triethylamine; dicyclohexyl-carbodiimide; trifluoroacetic anhydride; zinc(II) chloride; palladium on activated charcoal; In tetrahydrofuran; methanol; hexane; dichloromethane; toluene;

DOI:10.1021/ol060531d

Reference yield:

C39H71IO9Si3 (892859-20-0) → 2-(4-methoxy-phenyl)-4-phenyl-oxazolidine-3,5-dicarboxylic acid 3-tert-butyl ester 5-(4,10-diacetoxy-2-benzoyloxy-1-hydroxy-4,8,12,15,15-pentamethyl-5,9-dioxo-7-triethylsilanyloxy-tricyclo[9.3.1.03,8]pentadec-11-en-13-yl) ester (892859-28-8)

Guidance literature:

Multi-step reaction with 8 steps

1: 85 percent / H₂; pyridine / Pd/C / methanol / 24 h

2: 86 percent / DMSO; trifluoroacetic anhydride; Et₃N / CH₂Cl₂ / 1 h / -60 - -40 °C

3: 68 percent / 4-DMAP / CH₂Cl₂ / 19 h / 20 °C

4: 88 percent / tetrahydrofuran; hexane / 0.5 h / -72 °C

5: 85 percent / hydrogen fluoride/pyridine; pyridine / tetrahydrofuran / 17 h / 20 °C

6: 58 percent / ZnCl₂ / tetrahydrofuran / 0.5 h / 20 °C

7: 20 percent / pyridine; DMAP / 5 h / 60 °C

8: 54 percent / DCC; DMAP / toluene / 10 h / 70 °C

With pyridine; dmap; hydrogen fluoride; hydrogen; dimethyl sulfoxide; triethylamine; dicyclohexyl-carbodiimide; trifluoroacetic anhydride; zinc(II) chloride; palladium on activated charcoal; In tetrahydrofuran; methanol; hexane; dichloromethane; toluene;

DOI:10.1021/ol060531d

upstream raw materials:

Benzoic acid (1S,2S,3R,4R,7S,8S,10R,13S)-4,10-diacetoxy-1,13-dihydroxy-4,8,12,15,15-pentamethyl-5,9-dioxo-7-triethylsilanyloxy-tricyclo[9.3.1.0^3,8]pentadec-11-en-2-yl ester

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

Benzoic acid (1S,2S,3R,4R,7S,8S,10R,13S)-4-acetoxy-1,7,10,13-tetrahydroxy-4,8,12,15,15-pentamethyl-5,9-dioxo-tricyclo[9.3.1.0^3,8]pentadec-11-en-2-yl ester

Benzoic acid (1S,2S,3R,4R,7S,8S,10R,13S)-4,10-diacetoxy-1,7,13-trihydroxy-4,8,12,15,15-pentamethyl-5,9-dioxo-tricyclo[9.3.1.0^3,8]pentadec-11-en-2-yl ester

Downstream raw materials:

(2R,4S,5R)-2-(4-Methoxy-phenyl)-4-phenyl-oxazolidine-3,5-dicarboxylic acid 3-tert-butyl ester 5-((1S,2S,3R,4R,7S,8S,10R,13S)-4,10-diacetoxy-2-benzoyloxy-1,7-dihydroxy-4,8,12,15,15-pentamethyl-5,9-dioxo-tricyclo[9.3.1.0^3,8]pentadec-11-en-13-yl) ester

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