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

Base Information

• Chemical Name: 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
• CAS No.: 344550-02-3
• Molecular Formula: C₅₅H₆₅NO₁₅Si
• Molecular Weight: 1008.2

Synonyms: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

Chemical Property of 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

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Technology Process of 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

There total 1 articles about 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 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: 38.0%

acetic anhydride (108-24-7) + 20-acetyl-2'-O-(tert-butyldimethylsilyl)-4-deacetyl-5,6-dehydro-7-oxo-5-O-secopaclitaxel (344549-99-1) → Benzoic acid (1S,2S,3R,4S,8S,10R,13S)-2,10-diacetoxy-4-acetoxymethyl-13-[(2R,3S)-3-benzoylamino-2-(tert-butyl-dimethyl-silanyloxy)-3-phenyl-propionyloxy]-4-hydroxy-8,12,15,15-tetramethyl-7,9-dioxo-tricyclo[9.3.1.03,8]pentadeca-5,11-dien-1-yl ester + 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 4,9,10-triacetoxy-4-acetoxymethyl-13-[3-benzoylamino-2-(tert-butyl-dimethyl-silanyloxy)-3-phenyl-propionyloxy]-1-hydroxy-8,12,15,15-tetramethyl-7-oxo-tricyclo[9.3.1.03,8]pentadeca-5,9,11-trien-2-yl ester

Guidance literature:

With dmap; In toluene; at 80 ℃; for 17h;

DOI:10.1021/jo0015467

Reference yield: 71.0%

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 (1S,2S,3R,4S,8S,10R,13S)-4,10-diacetoxy-4-acetoxymethyl-13-((2R,3S)-3-benzoylamino-2-hydroxy-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

Guidance literature:

With pyridine hydrogenfluoride; In pyridine; at 20 ℃; for 3h;

DOI:10.1021/jo0015467

Reference yield: 28.0%

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]-1,7-dihydroxy-8,12,15,15-tetramethyl-9-oxo-tricyclo[9.3.1.03,8]pentadeca-5,11-dien-2-yl ester + 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)

Guidance literature:

With sodium tetrahydroborate; In tetrahydrofuran; methanol; at 0 ℃; for 0.416667h;

DOI:10.1021/jo0015467

upstream raw materials:

acetic anhydride

20-acetyl-2'-O-(tert-butyldimethylsilyl)-4-deacetyl-5,6-dehydro-7-oxo-5-O-secopaclitaxel

Downstream raw materials:

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

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

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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