Benzoic acid (1S,2S,9R,10R,13S)-9,10-diacetoxy-1,13-dihydroxy-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 (1S,2S,9R,10R,13S)-9,10-diacetoxy-1,13-dihydroxy-12,15,15-trimethyl-tricyclo[9.3.1.0^3,8]pentadeca-3⁽⁸⁾,4,6,11-tetraen-2-yl ester
• CAS No.: 155192-70-4
• Molecular Formula: C₂₉H₃₂O₈
• Molecular Weight: 508.568
• Mol file: 155192-70-4.mol

Synonyms:Benzoic acid (1S,2S,9R,10R,13S)-9,10-diacetoxy-1,13-dihydroxy-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 (1S,2S,9R,10R,13S)-9,10-diacetoxy-1,13-dihydroxy-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 (1S,2S,9R,10R,13S)-9,10-diacetoxy-1,13-dihydroxy-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 (1S,2S,9R,10R,13S)-9,10-diacetoxy-1,13-dihydroxy-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:

Benzoic acid (1S,2S,9R,10R)-9,10-diacetoxy-1-hydroxy-12,15,15-trimethyl-13-oxo-tricyclo[9.3.1.03,8]pentadeca-3(8),4,6,11-tetraen-2-yl ester (155192-69-1) → Benzoic acid (1S,2S,9R,10R,13S)-9,10-diacetoxy-1,13-dihydroxy-12,15,15-trimethyl-tricyclo[9.3.1.03,8]pentadeca-3(8),4,6,11-tetraen-2-yl ester (155192-70-4) + Benzoic acid (1S,2S,9R,10R,13R)-9,10-diacetoxy-1,13-dihydroxy-12,15,15-trimethyl-tricyclo[9.3.1.03,8]pentadeca-3(8),4,6,11-tetraen-2-yl ester

Guidance literature:

With sodium tetrahydroborate; In methanol; at 0 ℃; for 0.333333h;

DOI:10.1021/ja00083a063

Reference yield:

phenyllithium (591-51-5) → Benzoic acid (1S,2S,9R,10R,13S)-9,10-diacetoxy-1,13-dihydroxy-12,15,15-trimethyl-tricyclo[9.3.1.03,8]pentadeca-3(8),4,6,11-tetraen-2-yl ester (155192-70-4)

Guidance literature:

Multi-step reaction with 4 steps

1: tetrahydrofuran / 0.5 h / -78 °C

2: Et₃N, DMAP / CH₂Cl₂ / 1 h / 25 °C

3: PCC, celite, NaOAc / benzene / 2 h / Heating

4: NaBH₄ / methanol / 0.33 h / 0 °C

With dmap; sodium tetrahydroborate; Celite; sodium acetate; triethylamine; pyridinium chlorochromate; In tetrahydrofuran; methanol; dichloromethane; benzene;

DOI:10.1021/ja00083a063

Reference yield:

2-(tert-butyldimethylsiloxymethyl)-4-(2,4,6-triisoporpyl-benzenesulfonyl-hydrazono)-1,3,3-trimethyl-cyclohex-1-ene (150966-64-6) → Benzoic acid (1S,2S,9R,10R,13S)-9,10-diacetoxy-1,13-dihydroxy-12,15,15-trimethyl-tricyclo[9.3.1.03,8]pentadeca-3(8),4,6,11-tetraen-2-yl ester (155192-70-4)

Guidance literature:

Multi-step reaction with 13 steps

1: 1.) n-BuLi / 1.) THF, from -78 deg C to 25 deg C, 2.) THF, 0 deg C, 30 min

2: 90 percent / t-BuOOH, VO(acac)2 / benzene / 5 h / 25 °C

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

4: 100 percent / imidazole / CH₂Cl₂ / 1 h / 25 °C

5: 95 percent / acetonitrile / 2 h / Heating

6: 100 percent / TBAF / tetrahydrofuran / 2 h / 25 °C

7: 89 percent / tetrapropylammonium perruthenate, N-methylmorpholine N-oxide monohydrate / CH₂Cl₂ / 25 °C

8: 53 percent / TiCl₃, Zn-Cu / 1,2-dimethoxy-ethane / 2 h / 5 °C / Heating

10: tetrahydrofuran / 0.5 h / -78 °C

11: Et₃N, DMAP / CH₂Cl₂ / 1 h / 25 °C

12: PCC, celite, NaOAc / benzene / 2 h / Heating

13: NaBH₄ / methanol / 0.33 h / 0 °C

With 1H-imidazole; tert.-butylhydroperoxide; dmap; sodium tetrahydroborate; lithium aluminium tetrahydride; n-butyllithium; titanium(III) chloride; tetrapropylammonium perruthennate; bis(acetylacetonate)oxovanadium; Celite; tetrabutyl ammonium fluoride; sodium acetate; copper; 4-methylmorpholine N-oxide; triethylamine; pyridinium chlorochromate; zinc; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; diethyl ether; dichloromethane; acetonitrile; benzene;

DOI:10.1021/ja00083a063

upstream raw materials:

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

phenyllithium

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

C₁₉H₂₂O₅

Downstream raw materials:

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