benzoic acid 4,10-diacetoxy-4-acetoxymethyl-13-[3-benzoylamino-2-(tert-butyl-dimethyl-silanyloxy)-3-phenyl-propionyloxy]-1-hydroxy-8,12,15,15-tetramethyl-7-methylsulfanylthiocarboxyoxy-9-oxo-tricyclo[9.3.1.0^3,8]pentadec-11-en-2-yl ester

Base Information

• Chemical Name: benzoic acid 4,10-diacetoxy-4-acetoxymethyl-13-[3-benzoylamino-2-(tert-butyl-dimethyl-silanyloxy)-3-phenyl-propionyloxy]-1-hydroxy-8,12,15,15-tetramethyl-7-methylsulfanylthiocarboxyoxy-9-oxo-tricyclo[9.3.1.0^3,8]pentadec-11-en-2-yl ester
• CAS No.: 344550-11-4
• Molecular Formula: C₅₇H₇₁NO₁₅S₂Si
• Molecular Weight: 1102.41

Synonyms:benzoic acid 4,10-diacetoxy-4-acetoxymethyl-13-[3-benzoylamino-2-(tert-butyl-dimethyl-silanyloxy)-3-phenyl-propionyloxy]-1-hydroxy-8,12,15,15-tetramethyl-7-methylsulfanylthiocarboxyoxy-9-oxo-tricyclo[9.3.1.0^3,8]pentadec-11-en-2-yl ester

Chemical Property of benzoic acid 4,10-diacetoxy-4-acetoxymethyl-13-[3-benzoylamino-2-(tert-butyl-dimethyl-silanyloxy)-3-phenyl-propionyloxy]-1-hydroxy-8,12,15,15-tetramethyl-7-methylsulfanylthiocarboxyoxy-9-oxo-tricyclo[9.3.1.0^3,8]pentadec-11-en-2-yl ester

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Technology Process of benzoic acid 4,10-diacetoxy-4-acetoxymethyl-13-[3-benzoylamino-2-(tert-butyl-dimethyl-silanyloxy)-3-phenyl-propionyloxy]-1-hydroxy-8,12,15,15-tetramethyl-7-methylsulfanylthiocarboxyoxy-9-oxo-tricyclo[9.3.1.0^3,8]pentadec-11-en-2-yl ester

There total 2 articles about benzoic acid 4,10-diacetoxy-4-acetoxymethyl-13-[3-benzoylamino-2-(tert-butyl-dimethyl-silanyloxy)-3-phenyl-propionyloxy]-1-hydroxy-8,12,15,15-tetramethyl-7-methylsulfanylthiocarboxyoxy-9-oxo-tricyclo[9.3.1.0^3,8]pentadec-11-en-2-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: 70.0%

carbon disulfide (75-15-0,12122-00-8) + Benzoic acid (1S,2S,3R,4S,7R,8S,10R,13S)-4,10-diacetoxy-4-acetoxymethyl-13-[(2R,3S)-3-benzoylamino-2-(tert-butyl-dimethyl-silanyloxy)-3-phenyl-propionyloxy]-1,7-dihydroxy-8,12,15,15-tetramethyl-9-oxo-tricyclo[9.3.1.03,8]pentadec-11-en-2-yl ester (344550-09-0) + methyl iodide (74-88-4) → benzoic acid 4,10-diacetoxy-4-acetoxymethyl-13-[3-benzoylamino-2-(tert-butyl-dimethyl-silanyloxy)-3-phenyl-propionyloxy]-1-hydroxy-8,12,15,15-tetramethyl-7-methylsulfanylthiocarboxyoxy-9-oxo-tricyclo[9.3.1.03,8]pentadec-11-en-2-yl ester (344550-11-4)

Guidance literature:

Benzoic acid (1S,2S,3R,4S,7R,8S,10R,13S)-4,10-diacetoxy-4-acetoxymethyl-13-[(2R,3S)-3-benzoylamino-2-(tert-butyl-dimethyl-silanyloxy)-3-phenyl-propionyloxy]-1,7-dihydroxy-8,12,15,15-tetramethyl-9-oxo-tricyclo[9.3.1.0^3,8]pentadec-11-en-2-yl ester; With sodium hydride; In tetrahydrofuran; at 20 ℃; for 0.0833333h;

carbon disulfide; methyl iodide; In tetrahydrofuran; at 20 ℃; for 0.25h; Further stages.;

DOI:10.1021/jo0015467

Reference yield:

Benzoic acid (1S,2S,3R,4S,8S,10R,13S)-4,10-diacetoxy-4-acetoxymethyl-13-[(2R,3S)-3-benzoylamino-2-(tert-butyl-dimethyl-silanyloxy)-3-phenyl-propionyloxy]-1-hydroxy-8,12,15,15-tetramethyl-7,9-dioxo-tricyclo[9.3.1.03,8]pentadeca-5,11-dien-2-yl ester (344550-02-3) → benzoic acid 4,10-diacetoxy-4-acetoxymethyl-13-[3-benzoylamino-2-(tert-butyl-dimethyl-silanyloxy)-3-phenyl-propionyloxy]-1-hydroxy-8,12,15,15-tetramethyl-7-methylsulfanylthiocarboxyoxy-9-oxo-tricyclo[9.3.1.03,8]pentadec-11-en-2-yl ester (344550-11-4)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 38 percent / NaBH₄ / methanol; tetrahydrofuran / 0.42 h / 0 °C

2.1: NaH / tetrahydrofuran / 0.08 h / 20 °C

2.2: 70 percent / tetrahydrofuran / 0.25 h / 20 °C

With sodium tetrahydroborate; sodium hydride; In tetrahydrofuran; methanol;

DOI:10.1021/jo0015467

Reference yield: 71.0%

benzoic acid 4,10-diacetoxy-4-acetoxymethyl-13-[3-benzoylamino-2-(tert-butyl-dimethyl-silanyloxy)-3-phenyl-propionyloxy]-1-hydroxy-8,12,15,15-tetramethyl-7-methylsulfanylthiocarboxyoxy-9-oxo-tricyclo[9.3.1.03,8]pentadec-11-en-2-yl ester (344550-11-4) → Benzoic acid (1S,2S,3R,4S,7S,8S,10R,13S)-4,10-diacetoxy-4-acetoxymethyl-13-[(2R,3S)-3-benzoylamino-2-(tert-butyl-dimethyl-silanyloxy)-3-phenyl-propionyloxy]-1,7-dihydroxy-8,12,15,15-tetramethyl-9-oxo-tricyclo[9.3.1.03,8]pentadec-11-en-2-yl ester (344550-12-5)

Guidance literature:

With 2,2'-azobis(isobutyronitrile); water; tri-n-butyl-tin hydride; In toluene; at 75 ℃; for 1h;

DOI:10.1021/jo0015467

upstream raw materials:

carbon disulfide

Benzoic acid (1S,2S,3R,4S,7R,8S,10R,13S)-4,10-diacetoxy-4-acetoxymethyl-13-[(2R,3S)-3-benzoylamino-2-(tert-butyl-dimethyl-silanyloxy)-3-phenyl-propionyloxy]-1,7-dihydroxy-8,12,15,15-tetramethyl-9-oxo-tricyclo[9.3.1.0^3,8]pentadec-11-en-2-yl ester

methyl iodide

Benzoic acid (1S,2S,3R,4S,8S,10R,13S)-4,10-diacetoxy-4-acetoxymethyl-13-[(2R,3S)-3-benzoylamino-2-(tert-butyl-dimethyl-silanyloxy)-3-phenyl-propionyloxy]-1-hydroxy-8,12,15,15-tetramethyl-7,9-dioxo-tricyclo[9.3.1.0^3,8]pentadeca-5,11-dien-2-yl ester

Downstream raw materials:

Benzoic acid (1S,2S,3R,4S,7S,8S,10R,13S)-4,10-diacetoxy-4-acetoxymethyl-13-[(2R,3S)-3-benzoylamino-2-(tert-butyl-dimethyl-silanyloxy)-3-phenyl-propionyloxy]-1,7-dihydroxy-8,12,15,15-tetramethyl-9-oxo-tricyclo[9.3.1.0^3,8]pentadec-11-en-2-yl ester

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