Benzoic acid (1R,2R,9S,10S,13R)-9,10-diacetoxy-13-((2R,3S)-3-benzoylamino-3-phenyl-2-triethylsilanyloxy-propionyloxy)-1-hydroxy-4-methoxy-12,15,15-trimethyl-tricyclo[9.3.1.0^3,8]pentadeca-3⁽⁸⁾,4,6,11-tetraen-2-yl ester

Base Information

• Chemical Name: Benzoic acid (1R,2R,9S,10S,13R)-9,10-diacetoxy-13-((2R,3S)-3-benzoylamino-3-phenyl-2-triethylsilanyloxy-propionyloxy)-1-hydroxy-4-methoxy-12,15,15-trimethyl-tricyclo[9.3.1.0^3,8]pentadeca-3⁽⁸⁾,4,6,11-tetraen-2-yl ester
• CAS No.: 189166-82-3
• Molecular Formula: C₅₂H₆₁NO₁₂Si
• Molecular Weight: 920.141

Synonyms:Benzoic acid (1R,2R,9S,10S,13R)-9,10-diacetoxy-13-((2R,3S)-3-benzoylamino-3-phenyl-2-triethylsilanyloxy-propionyloxy)-1-hydroxy-4-methoxy-12,15,15-trimethyl-tricyclo[9.3.1.0^3,8]pentadeca-3⁽⁸⁾,4,6,11-tetraen-2-yl ester

Chemical Property of Benzoic acid (1R,2R,9S,10S,13R)-9,10-diacetoxy-13-((2R,3S)-3-benzoylamino-3-phenyl-2-triethylsilanyloxy-propionyloxy)-1-hydroxy-4-methoxy-12,15,15-trimethyl-tricyclo[9.3.1.0^3,8]pentadeca-3⁽⁸⁾,4,6,11-tetraen-2-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Benzoic acid (1R,2R,9S,10S,13R)-9,10-diacetoxy-13-((2R,3S)-3-benzoylamino-3-phenyl-2-triethylsilanyloxy-propionyloxy)-1-hydroxy-4-methoxy-12,15,15-trimethyl-tricyclo[9.3.1.0^3,8]pentadeca-3⁽⁸⁾,4,6,11-tetraen-2-yl ester

There total 15 articles about Benzoic acid (1R,2R,9S,10S,13R)-9,10-diacetoxy-13-((2R,3S)-3-benzoylamino-3-phenyl-2-triethylsilanyloxy-propionyloxy)-1-hydroxy-4-methoxy-12,15,15-trimethyl-tricyclo[9.3.1.0^3,8]pentadeca-3⁽⁸⁾,4,6,11-tetraen-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: 37.0%

(3R,4S)-1-benzoyl-4-phenyl-3-(triethylsilyl)oxy-2-azetidinone (149249-91-2) + Benzoic acid (1R,2R,9S,10S,13R)-9,10-diacetoxy-1,13-dihydroxy-4-methoxy-12,15,15-trimethyl-tricyclo[9.3.1.03,8]pentadeca-3(8),4,6,11-tetraen-2-yl ester → Benzoic acid (1R,2R,9S,10S,13R)-9,10-diacetoxy-13-((2R,3S)-3-benzoylamino-3-phenyl-2-triethylsilanyloxy-propionyloxy)-1-hydroxy-4-methoxy-12,15,15-trimethyl-tricyclo[9.3.1.03,8]pentadeca-3(8),4,6,11-tetraen-2-yl ester (189166-82-3) + Benzoic acid (1S,2S,9R,10R,13S)-9,10-diacetoxy-13-((2R,3S)-3-benzoylamino-3-phenyl-2-triethylsilanyloxy-propionyloxy)-1-hydroxy-4-methoxy-12,15,15-trimethyl-tricyclo[9.3.1.03,8]pentadeca-3(8),4,6,11-tetraen-2-yl ester (189166-81-2)

Guidance literature:

With sodium hexamethyldisilazane; In tetrahydrofuran; at -78 ℃; for 0.5h;

DOI:10.1002/chem.19970030311

Reference yield:

3-methoxy-o-xylene-α,α'-diol (90047-52-2) → Benzoic acid (1R,2R,9S,10S,13R)-9,10-diacetoxy-13-((2R,3S)-3-benzoylamino-3-phenyl-2-triethylsilanyloxy-propionyloxy)-1-hydroxy-4-methoxy-12,15,15-trimethyl-tricyclo[9.3.1.03,8]pentadeca-3(8),4,6,11-tetraen-2-yl ester (189166-82-3)

Guidance literature:

Multi-step reaction with 13 steps

1: 33 percent / imidazole / CH₂Cl₂ / 1 h / 0 °C

2: 86 percent / PDC, molecular sieves 4 Angstroem / CH₂Cl₂ / 1.) 0 deg C, 30 min, 2.) 25 deg C, 2 h

3: 85 percent / n-BuLi / tetrahydrofuran; hexane / 1.) -78 to 25 deg C, 2.) 0 deg C, 0.5 h

4: 86 percent / t-BuOOH / VO(acac)2 / benzene; 2,2,4-trimethyl-pentane / 5 h / 25 °C

5: 75 percent / LiAlH₄ / diethyl ether / 4 h / Heating

6: 73 percent / acetonitrile / 2 h / Heating

7: 69 percent / tetrapropylammonium perruthenate, NMO / CH₂Cl₂ / 1 h / 25 °C

8: 37 percent / 3(dme)1.5>, Zn/Cu, Et₃N / 1,2-dimethoxy-ethane / 1.) reflux, 3 h, 2.) 55 deg C, 3 h

9: 78 percent / cyclohexane; tetrahydrofuran; diethyl ether / 0.5 h / -78 °C

10: 97 percent / NEt₃, DMAP / CH₂Cl₂ / 1 h / 25 °C

11: 53 percent / PCC, Celite, AcONa / benzene / 70 °C

12: 43 percent / NaBH₄ / methanol / 0.33 h / 0 °C

13: NaN(SiMe₃)2 / tetrahydrofuran / 0.5 h / -78 °C

With 1H-imidazole; tert.-butylhydroperoxide; dmap; sodium tetrahydroborate; lithium aluminium tetrahydride; dipyridinium dichromate; n-butyllithium; N-methyl-2-indolinone; tetrapropylammonium perruthennate; ; 4 A molecular sieve; Celite; sodium acetate; sodium hexamethyldisilazane; copper; triethylamine; pyridinium chlorochromate; zinc; bis(acetylacetonate)oxovanadium; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; 2,2,4-trimethylpentane; diethyl ether; hexane; dichloromethane; cyclohexane; acetonitrile; benzene;

DOI:10.1002/chem.19970030311

Reference yield:

2-(tert-butyldimethylsiloxymethyl)-4-(2,4,6-triisoporpyl-benzenesulfonyl-hydrazono)-1,3,3-trimethyl-cyclohex-1-ene (150966-64-6) → Benzoic acid (1R,2R,9S,10S,13R)-9,10-diacetoxy-13-((2R,3S)-3-benzoylamino-3-phenyl-2-triethylsilanyloxy-propionyloxy)-1-hydroxy-4-methoxy-12,15,15-trimethyl-tricyclo[9.3.1.03,8]pentadeca-3(8),4,6,11-tetraen-2-yl ester (189166-82-3)

Guidance literature:

Multi-step reaction with 11 steps

1: 85 percent / n-BuLi / tetrahydrofuran; hexane / 1.) -78 to 25 deg C, 2.) 0 deg C, 0.5 h

2: 86 percent / t-BuOOH / VO(acac)2 / benzene; 2,2,4-trimethyl-pentane / 5 h / 25 °C

3: 75 percent / LiAlH₄ / diethyl ether / 4 h / Heating

4: 73 percent / acetonitrile / 2 h / Heating

5: 69 percent / tetrapropylammonium perruthenate, NMO / CH₂Cl₂ / 1 h / 25 °C

6: 37 percent / 3(dme)1.5>, Zn/Cu, Et₃N / 1,2-dimethoxy-ethane / 1.) reflux, 3 h, 2.) 55 deg C, 3 h

7: 78 percent / cyclohexane; tetrahydrofuran; diethyl ether / 0.5 h / -78 °C

8: 97 percent / NEt₃, DMAP / CH₂Cl₂ / 1 h / 25 °C

9: 53 percent / PCC, Celite, AcONa / benzene / 70 °C

10: 43 percent / NaBH₄ / methanol / 0.33 h / 0 °C

11: NaN(SiMe₃)2 / tetrahydrofuran / 0.5 h / -78 °C

With tert.-butylhydroperoxide; dmap; sodium tetrahydroborate; lithium aluminium tetrahydride; n-butyllithium; N-methyl-2-indolinone; tetrapropylammonium perruthennate; ; Celite; sodium acetate; sodium hexamethyldisilazane; copper; triethylamine; pyridinium chlorochromate; zinc; bis(acetylacetonate)oxovanadium; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; 2,2,4-trimethylpentane; diethyl ether; hexane; dichloromethane; cyclohexane; acetonitrile; benzene;

DOI:10.1002/chem.19970030311

upstream raw materials:

(3R,4S)-1-benzoyl-4-phenyl-3-(triethylsilyl)oxy-2-azetidinone

3-methoxy-o-xylene-α,α'-diol

phenyllithium

2-(tert-butyldimethylsiloxymethyl)-4-(2,4,6-triisoporpyl-benzenesulfonyl-hydrazono)-1,3,3-trimethyl-cyclohex-1-ene

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