(4R,5S)-2-(4-Methoxy-phenyl)-4-phenyl-oxazolidine-3,5-dicarboxylic acid 3-tert-butyl ester 5-((1R,5S,7S,8S,9R,10R,11S,12S)-7,9,10-triacetoxy-4-acetoxymethyl-8,12,15,15-tetramethyl-13-oxo-tricyclo[9.3.1.0^3,8]pentadec-3-en-5-yl) ester

Base Information

• Chemical Name: (4R,5S)-2-(4-Methoxy-phenyl)-4-phenyl-oxazolidine-3,5-dicarboxylic acid 3-tert-butyl ester 5-((1R,5S,7S,8S,9R,10R,11S,12S)-7,9,10-triacetoxy-4-acetoxymethyl-8,12,15,15-tetramethyl-13-oxo-tricyclo[9.3.1.0^3,8]pentadec-3-en-5-yl) ester
• CAS No.: 445473-98-3
• Molecular Formula: C₅₀H₆₃NO₁₅
• Molecular Weight: 918.048

Synonyms:(4R,5S)-2-(4-Methoxy-phenyl)-4-phenyl-oxazolidine-3,5-dicarboxylic acid 3-tert-butyl ester 5-((1R,5S,7S,8S,9R,10R,11S,12S)-7,9,10-triacetoxy-4-acetoxymethyl-8,12,15,15-tetramethyl-13-oxo-tricyclo[9.3.1.0^3,8]pentadec-3-en-5-yl) ester

Chemical Property of (4R,5S)-2-(4-Methoxy-phenyl)-4-phenyl-oxazolidine-3,5-dicarboxylic acid 3-tert-butyl ester 5-((1R,5S,7S,8S,9R,10R,11S,12S)-7,9,10-triacetoxy-4-acetoxymethyl-8,12,15,15-tetramethyl-13-oxo-tricyclo[9.3.1.0^3,8]pentadec-3-en-5-yl) ester

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Technology Process of (4R,5S)-2-(4-Methoxy-phenyl)-4-phenyl-oxazolidine-3,5-dicarboxylic acid 3-tert-butyl ester 5-((1R,5S,7S,8S,9R,10R,11S,12S)-7,9,10-triacetoxy-4-acetoxymethyl-8,12,15,15-tetramethyl-13-oxo-tricyclo[9.3.1.0^3,8]pentadec-3-en-5-yl) ester

There total 3 articles about (4R,5S)-2-(4-Methoxy-phenyl)-4-phenyl-oxazolidine-3,5-dicarboxylic acid 3-tert-butyl ester 5-((1R,5S,7S,8S,9R,10R,11S,12S)-7,9,10-triacetoxy-4-acetoxymethyl-8,12,15,15-tetramethyl-13-oxo-tricyclo[9.3.1.0^3,8]pentadec-3-en-5-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: 29.0%

acide (4S,5R)-N-(tert-butoxycarbonyl)-2-(4-O-methoxyphenyl)-4-phenyl-5-oxazolidine carboxylique (196404-55-4) + Acetic acid (1R,5S,7S,8S,9R,10R,11S,12S)-7,10-diacetoxy-4-acetoxymethyl-5-hydroxy-8,12,15,15-tetramethyl-13-oxo-tricyclo[9.3.1.03,8]pentadec-3-en-9-yl ester (445473-96-1) → (4R,5S)-2-(4-Methoxy-phenyl)-4-phenyl-oxazolidine-3,5-dicarboxylic acid 3-tert-butyl ester 5-((1R,5S,7S,8S,9R,10R,11S,12S)-7,9,10-triacetoxy-4-acetoxymethyl-8,12,15,15-tetramethyl-13-oxo-tricyclo[9.3.1.03,8]pentadec-3-en-5-yl) ester (445473-98-3)

Guidance literature:

With dmap; dicyclohexyl-carbodiimide; In dichloromethane; toluene; at 75 ℃; for 5h;

DOI:10.1016/S0968-0896(02)00066-4

Reference yield:

5α-hydroxy-7β,9α,10β-triacetoxy-4(20),11(12)-taxadien-13-one (198631-40-2) → (4R,5S)-2-(4-Methoxy-phenyl)-4-phenyl-oxazolidine-3,5-dicarboxylic acid 3-tert-butyl ester 5-((1R,5S,7S,8S,9R,10R,11S,12S)-7,9,10-triacetoxy-4-acetoxymethyl-8,12,15,15-tetramethyl-13-oxo-tricyclo[9.3.1.03,8]pentadec-3-en-5-yl) ester (445473-98-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 13 percent / activated Zn / acetic acid / 25 h / 23 °C

2: 59 percent / pyridine / 18 h / 4 °C

3: 29 percent / DMAP; DCC / CH₂Cl₂; toluene / 5 h / 75 °C

With dmap; dicyclohexyl-carbodiimide; zinc; In pyridine; dichloromethane; acetic acid; toluene;

DOI:10.1016/S0968-0896(02)00066-4

Reference yield:

Acetic acid (1R,5S,7S,8S,9R,10R,11S,12S)-7,10-diacetoxy-5-hydroxy-4-hydroxymethyl-8,12,15,15-tetramethyl-13-oxo-tricyclo[9.3.1.03,8]pentadec-3-en-9-yl ester (445473-91-6) → (4R,5S)-2-(4-Methoxy-phenyl)-4-phenyl-oxazolidine-3,5-dicarboxylic acid 3-tert-butyl ester 5-((1R,5S,7S,8S,9R,10R,11S,12S)-7,9,10-triacetoxy-4-acetoxymethyl-8,12,15,15-tetramethyl-13-oxo-tricyclo[9.3.1.03,8]pentadec-3-en-5-yl) ester (445473-98-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 59 percent / pyridine / 18 h / 4 °C

2: 29 percent / DMAP; DCC / CH₂Cl₂; toluene / 5 h / 75 °C

With dmap; dicyclohexyl-carbodiimide; In pyridine; dichloromethane; toluene;

DOI:10.1016/S0968-0896(02)00066-4

upstream raw materials:

acide (4S,5R)-N-(tert-butoxycarbonyl)-2-(4-O-methoxyphenyl)-4-phenyl-5-oxazolidine carboxylique

Acetic acid (1R,5S,7S,8S,9R,10R,11S,12S)-7,10-diacetoxy-4-acetoxymethyl-5-hydroxy-8,12,15,15-tetramethyl-13-oxo-tricyclo[9.3.1.0^3,8]pentadec-3-en-9-yl ester

5α-hydroxy-7β,9α,10β-triacetoxy-4(20),11(12)-taxadien-13-one

Acetic acid (1R,5S,7S,8S,9R,10R,11S,12S)-7,10-diacetoxy-5-hydroxy-4-hydroxymethyl-8,12,15,15-tetramethyl-13-oxo-tricyclo[9.3.1.0^3,8]pentadec-3-en-9-yl ester

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