(2R,4S,5R)-3-Benzoyl-2-(4-methoxy-phenyl)-4-phenyl-oxazolidine-5-carboxylic acid (1S,2S,3R,10R,11R,12R,15S)-11,12-diacetoxy-2-benzoyloxy-1-hydroxy-10,14,17,17-tetramethyl-4-oxo-6-oxa-tricyclo[11.3.1.0^3,10]heptadec-13-en-15-yl ester

Base Information

• Chemical Name: (2R,4S,5R)-3-Benzoyl-2-(4-methoxy-phenyl)-4-phenyl-oxazolidine-5-carboxylic acid (1S,2S,3R,10R,11R,12R,15S)-11,12-diacetoxy-2-benzoyloxy-1-hydroxy-10,14,17,17-tetramethyl-4-oxo-6-oxa-tricyclo[11.3.1.0^3,10]heptadec-13-en-15-yl ester
• CAS No.: 911285-72-8
• Molecular Formula: C₅₅H₅₉NO₁₄
• Molecular Weight: 958.072

Synonyms:(2R,4S,5R)-3-Benzoyl-2-(4-methoxy-phenyl)-4-phenyl-oxazolidine-5-carboxylic acid (1S,2S,3R,10R,11R,12R,15S)-11,12-diacetoxy-2-benzoyloxy-1-hydroxy-10,14,17,17-tetramethyl-4-oxo-6-oxa-tricyclo[11.3.1.0^3,10]heptadec-13-en-15-yl ester

Chemical Property of (2R,4S,5R)-3-Benzoyl-2-(4-methoxy-phenyl)-4-phenyl-oxazolidine-5-carboxylic acid (1S,2S,3R,10R,11R,12R,15S)-11,12-diacetoxy-2-benzoyloxy-1-hydroxy-10,14,17,17-tetramethyl-4-oxo-6-oxa-tricyclo[11.3.1.0^3,10]heptadec-13-en-15-yl ester

Chemical Property:

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Technology Process of (2R,4S,5R)-3-Benzoyl-2-(4-methoxy-phenyl)-4-phenyl-oxazolidine-5-carboxylic acid (1S,2S,3R,10R,11R,12R,15S)-11,12-diacetoxy-2-benzoyloxy-1-hydroxy-10,14,17,17-tetramethyl-4-oxo-6-oxa-tricyclo[11.3.1.0^3,10]heptadec-13-en-15-yl ester

There total 11 articles about (2R,4S,5R)-3-Benzoyl-2-(4-methoxy-phenyl)-4-phenyl-oxazolidine-5-carboxylic acid (1S,2S,3R,10R,11R,12R,15S)-11,12-diacetoxy-2-benzoyloxy-1-hydroxy-10,14,17,17-tetramethyl-4-oxo-6-oxa-tricyclo[11.3.1.0^3,10]heptadec-13-en-15-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: 93.0%

Benzoic acid (1S,2S,3R,10R,11R,12R,15S)-11,12-diacetoxy-1,15-dihydroxy-10,14,17,17-tetramethyl-4-oxo-6-oxa-tricyclo[11.3.1.03,10]heptadec-13-en-2-yl ester (862251-87-4) + (2R,4S,5R)-3-benzoyl-2-(4-methoxyphenyl)-4-phenyl-1,3-oxazolidine-5-carboxylic acid (157826-10-3,949023-16-9) → (2R,4S,5R)-3-Benzoyl-2-(4-methoxy-phenyl)-4-phenyl-oxazolidine-5-carboxylic acid (1S,2S,3R,10R,11R,12R,15S)-11,12-diacetoxy-2-benzoyloxy-1-hydroxy-10,14,17,17-tetramethyl-4-oxo-6-oxa-tricyclo[11.3.1.03,10]heptadec-13-en-15-yl ester (911285-72-8)

Guidance literature:

With dmap; dicyclohexyl-carbodiimide; In toluene; at 75 ℃; for 0.5h;

DOI:10.1016/j.tetlet.2005.05.071

Reference yield:

C25H31BrO10 (862251-84-1) → (2R,4S,5R)-3-Benzoyl-2-(4-methoxy-phenyl)-4-phenyl-oxazolidine-5-carboxylic acid (1S,2S,3R,10R,11R,12R,15S)-11,12-diacetoxy-2-benzoyloxy-1-hydroxy-10,14,17,17-tetramethyl-4-oxo-6-oxa-tricyclo[11.3.1.03,10]heptadec-13-en-15-yl ester (911285-72-8)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 60 percent / Bu₃SnH; AIBN / benzene / 0.25 h / Irradiation

2.1: tetrahydrofuran / -80 °C

2.2: 62 percent / DMAP / CH₂Cl₂

3.1: 72 percent / NaBH₄ / methanol

4.1: 93 percent / DMAP; DCC / toluene / 0.5 h / 75 °C

With dmap; sodium tetrahydroborate; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; dicyclohexyl-carbodiimide; In tetrahydrofuran; methanol; toluene; benzene;

DOI:10.1016/j.tetlet.2005.05.071

Reference yield:

C25H32O10 (862251-86-3) → (2R,4S,5R)-3-Benzoyl-2-(4-methoxy-phenyl)-4-phenyl-oxazolidine-5-carboxylic acid (1S,2S,3R,10R,11R,12R,15S)-11,12-diacetoxy-2-benzoyloxy-1-hydroxy-10,14,17,17-tetramethyl-4-oxo-6-oxa-tricyclo[11.3.1.03,10]heptadec-13-en-15-yl ester (911285-72-8)

Guidance literature:

Multi-step reaction with 3 steps

1.1: tetrahydrofuran / -80 °C

1.2: 62 percent / DMAP / CH₂Cl₂

2.1: 72 percent / NaBH₄ / methanol

3.1: 93 percent / DMAP; DCC / toluene / 0.5 h / 75 °C

With dmap; sodium tetrahydroborate; dicyclohexyl-carbodiimide; In tetrahydrofuran; methanol; toluene;

DOI:10.1016/j.tetlet.2005.05.071

upstream raw materials:

Benzoic acid (1S,2S,3R,10R,11R,12R,15S)-11,12-diacetoxy-1,15-dihydroxy-10,14,17,17-tetramethyl-4-oxo-6-oxa-tricyclo[11.3.1.0^3,10]heptadec-13-en-2-yl ester

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

C₂₅H₃₂O₁₀

C₂₅H₃₁BrO₁₀

Downstream raw materials:

Benzoic acid (1S,2S,3R,10R,11R,12R,15S)-11,12-diacetoxy-15-((2R,3S)-3-benzoylamino-2-hydroxy-3-phenyl-propionyloxy)-1-hydroxy-10,14,17,17-tetramethyl-4-oxo-6-oxa-tricyclo[11.3.1.0^3,10]heptadec-13-en-2-yl ester

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