Benzoic acid (2R,4aR,5R,8R,8aS)-5-((R)-1-carboxy-ethyl)-3,8-dimethyl-1,2,4a,5,6,7,8,8a-octahydro-naphthalen-2-yl ester

Base Information

• Chemical Name: Benzoic acid (2R,4aR,5R,8R,8aS)-5-((R)-1-carboxy-ethyl)-3,8-dimethyl-1,2,4a,5,6,7,8,8a-octahydro-naphthalen-2-yl ester
• CAS No.: 174626-86-9
• Molecular Formula: C₂₂H₂₈O₄
• Molecular Weight: 356.462
• Mol file: 174626-86-9.mol

Synonyms:Benzoic acid (2R,4aR,5R,8R,8aS)-5-((R)-1-carboxy-ethyl)-3,8-dimethyl-1,2,4a,5,6,7,8,8a-octahydro-naphthalen-2-yl ester

Chemical Property of Benzoic acid (2R,4aR,5R,8R,8aS)-5-((R)-1-carboxy-ethyl)-3,8-dimethyl-1,2,4a,5,6,7,8,8a-octahydro-naphthalen-2-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Benzoic acid (2R,4aR,5R,8R,8aS)-5-((R)-1-carboxy-ethyl)-3,8-dimethyl-1,2,4a,5,6,7,8,8a-octahydro-naphthalen-2-yl ester

There total 14 articles about Benzoic acid (2R,4aR,5R,8R,8aS)-5-((R)-1-carboxy-ethyl)-3,8-dimethyl-1,2,4a,5,6,7,8,8a-octahydro-naphthalen-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:

(1R,3R,8S,9R)-(+)-3-carbomethoxy-6,10,10-trimethyltricyclo<7.1.1.o3,8>undec-5-en-2-one (135260-67-2) → Benzoic acid (2R,4aR,5R,8R,8aS)-5-((R)-1-carboxy-ethyl)-3,8-dimethyl-1,2,4a,5,6,7,8,8a-octahydro-naphthalen-2-yl ester (174626-86-9)

Guidance literature:

Multi-step reaction with 14 steps

1: 90 percent / O₂, 5,10,15,20-tetraphenyl-21H,23H-porphine, Ac₂O, DMAP, pyridine / CH₂Cl₂ / 20 °C / Irradiation

2: 98 percent / boron trifluoride etherate / CH₂Cl₂ / -10 °C

3: 91 percent / lithium iodide monohydrate / various solvent(s) / Heating

4: p-toluenesulfonic acid / benzene / Heating

5: 1) p-toluenesulfonic acid, 2) aq. NaOH / 1) aq. acetone, reflux, 2) MeOH, reflux

6: 94 percent / potassium hydride, DMSO / benzene / 20 °C

7: 1) p-toluenesulfonic acid, 2) sodium hydroxide / 1) acetone, water, reflux, 2) methanol, water, 25 deg C

8: lithium aluminum hydride / tetrahydrofuran / Heating

9: Et₃N / CH₂Cl₂ / 0 °C

10: 92 percent / lithium aluminum hydride / tetrahydrofuran / Heating

11: 89 percent / HgCl₂ / acetonitrile; H₂O / 20 °C

12: 100 percent / sodium borohydride, cerium(III) chloride / methanol / -78 °C

13: 92 percent / triphenylphosphine, diethyl azodicarboxylate / tetrahydrofuran / 20 °C

14: 1) 9-borabicyclo<3.3.1>nonane, 2) H₂CrO₄ / 1) THF, 20 deg C, 2) ether, 0 -> 20 deg C

With pyridine; dmap; sodium hydroxide; sodium tetrahydroborate; lithium aluminium tetrahydride; 9-borabicyclo[3.3.1]nonane dimer; cerium(III) chloride; boron trifluoride diethyl etherate; oxygen; 5,15,10,20-tetraphenylporphyrin; acetic anhydride; chromic acid; potassium hydride; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; triphenylphosphine; mercury dichloride; lithium iodide; diethylazodicarboxylate; In tetrahydrofuran; methanol; dichloromethane; water; acetonitrile; benzene;

DOI:10.1016/0040-4039(93)88052-K

Reference yield:

(4aS,5R,8R,8aS)-5-Isopropenyl-3,8-dimethyl-4a,5,6,7,8,8a-hexahydro-1H-naphthalen-2-one (152451-90-6) → Benzoic acid (2R,4aR,5R,8R,8aS)-5-((R)-1-carboxy-ethyl)-3,8-dimethyl-1,2,4a,5,6,7,8,8a-octahydro-naphthalen-2-yl ester (174626-86-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 100 percent / sodium borohydride, cerium(III) chloride / methanol / -78 °C

2: 92 percent / triphenylphosphine, diethyl azodicarboxylate / tetrahydrofuran / 20 °C

3: 1) 9-borabicyclo<3.3.1>nonane, 2) H₂CrO₄ / 1) THF, 20 deg C, 2) ether, 0 -> 20 deg C

With sodium tetrahydroborate; 9-borabicyclo[3.3.1]nonane dimer; cerium(III) chloride; chromic acid; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; methanol;

DOI:10.1016/0040-4039(93)88052-K

Reference yield:

(2S,4aS,5R,8R,8aS)-5-Isopropenyl-3,8-dimethyl-1,2,4a,5,6,7,8,8a-octahydro-naphthalen-2-ol (152451-91-7) → Benzoic acid (2R,4aR,5R,8R,8aS)-5-((R)-1-carboxy-ethyl)-3,8-dimethyl-1,2,4a,5,6,7,8,8a-octahydro-naphthalen-2-yl ester (174626-86-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 92 percent / triphenylphosphine, diethyl azodicarboxylate / tetrahydrofuran / 20 °C

2: 1) 9-borabicyclo<3.3.1>nonane, 2) H₂CrO₄ / 1) THF, 20 deg C, 2) ether, 0 -> 20 deg C

With 9-borabicyclo[3.3.1]nonane dimer; chromic acid; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran;

DOI:10.1016/0040-4039(93)88052-K

upstream raw materials:

(1R,3R,8S,9R)-(+)-3-carbomethoxy-6,10,10-trimethyltricyclo<7.1.1.o^3,8>undec-5-en-2-one

(2S,4aS,5R,8R,8aS)-5-Isopropenyl-3,8-dimethyl-1,2,4a,5,6,7,8,8a-octahydro-naphthalen-2-ol

(4aS,5R,8R,8aS)-5-Isopropenyl-3,8-dimethyl-4a,5,6,7,8,8a-hexahydro-1H-naphthalen-2-one

C₁₇H₂₆S₂

Downstream raw materials:

C₁₂H₁₃O₂(CH₃)3(O)(OO)

C₂₂H₂₆O₆

Benzoic acid (R)-1-((1S,4R,4aS,7R,8S,8aR)-1-hydroxy-4,7-dimethyl-octahydro-isochromen-8-ylmethyl)-2-oxo-propyl ester

C₂₂H₂₈O₅