Benzoic acid (1S,3S)-1-((R)-1,2-dihydroxy-ethyl)-3,7-dimethyl-oct-6-enyl ester

Base Information

• Chemical Name: Benzoic acid (1S,3S)-1-((R)-1,2-dihydroxy-ethyl)-3,7-dimethyl-oct-6-enyl ester
• CAS No.: 342901-76-2
• Molecular Formula: C₁₉H₂₈O₄
• Molecular Weight: 320.429
• Mol file: 342901-76-2.mol

Synonyms:Benzoic acid (1S,3S)-1-((R)-1,2-dihydroxy-ethyl)-3,7-dimethyl-oct-6-enyl ester

Chemical Property of Benzoic acid (1S,3S)-1-((R)-1,2-dihydroxy-ethyl)-3,7-dimethyl-oct-6-enyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Benzoic acid (1S,3S)-1-((R)-1,2-dihydroxy-ethyl)-3,7-dimethyl-oct-6-enyl ester

There total 1 articles about Benzoic acid (1S,3S)-1-((R)-1,2-dihydroxy-ethyl)-3,7-dimethyl-oct-6-enyl 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:

ammonium benzoate (1863-63-4,21292-26-2,28271-83-2,143502-10-7) + [(2S,3R)-3-((S)-2,6-Dimethyl-hept-5-enyl)-oxiranyl]-methanol → Benzoic acid (1S,3S)-1-((R)-1,2-dihydroxy-ethyl)-3,7-dimethyl-oct-6-enyl ester (342901-76-2)

Guidance literature:

With titanium(IV) isopropylate; In dichloromethane; at 20 ℃;

DOI:10.1002/1521-3773(20010316)40:6<1090::AID-ANIE10900>3.0.CO;2-W

Reference yield:

Benzoic acid (1S,3S)-1-((R)-1,2-dihydroxy-ethyl)-3,7-dimethyl-oct-6-enyl ester (342901-76-2) → (2S,3R,5R,5aS,6aR,8R,10S,11R,12aS,13aR)-3,5-Bis-benzyloxy-2-(2-benzyloxy-ethyl)-11-hydroxymethyl-5a,8-dimethyl-tetradecahydro-1,6,12-trioxa-cyclohepta[4,5]benzo[1,2]cycloocten-10-ol (342901-89-7)

Guidance literature:

Multi-step reaction with 16 steps

1.1: 81 percent / KOH / methanol / 20 °C

2.1: 61 percent / camphorsulfonic acid / CH₂Cl₂ / 20 °C

3.1: OsO₄; N-methylmorpholine N-oxide / acetone; H₂O / 20 °C

3.2: 70 percent / NaIO₄ / acetone; H₂O

4.1: 95 percent / NaClO₂; KH₂PO₄; 2-methyl-2-butene / 2-methyl-propan-2-ol; H₂O / 20 °C

5.1: 2,4,6-trichlorobenzoyl chloride; Et₃N / tetrahydrofuran

5.2: 83 percent / DMAP / benzene / Heating

6.1: 95 percent / KHMDS / tetrahydrofuran; hexamethylphosphoric acid triamide / -78 °C

7.1: 9-BBN / tetrahydrofuran / 20 °C

7.2: 85 percent / 1 M aq. NaHCO₃ / [Pd(PPh₃)4] / dimethylformamide / 50 °C

8.1: 3,3-dimethyldioxirane / acetone / -78 - -20 °C

8.2: 60 percent / Et₃SiH; BH₃*THF / CH₂Cl₂ / -20 °C

9.1: 80 percent / t-BuOK; n-Bu₄NI / tetrahydrofuran / 20 °C

10.1: 97 percent / TBAF / tetrahydrofuran / 20 °C

11.1: 100 percent / tetrapropylammonium perruthenate; N-methylmorpholine N-oxide; 4 Angstroem molecular sieves / CH₂Cl₂ / 20 °C

12.1: DDQ / CH₂Cl₂; H₂O; various solvent(s) / 20 °C

13.1: Zn(OTf)2 / CH₂Cl₂ / 20 °C

14.1: DMAP; Et₃N / CH₂Cl₂ / 0 °C

15.1: 96 percent / mCPBA / CH₂Cl₂ / 20 °C

16.1: CH₂Cl₂ / -78 - 0 °C

16.2: 83 percent / K₂CO₃ / methanol / 20 °C

With dmap; potassium hydroxide; sodium chlorite; potassium dihydrogenphosphate; osmium(VIII) oxide; 9-borabicyclo[3.3.1]nonane dimer; tetrapropylammonium perruthennate; 2-methyl-but-2-ene; 4 A molecular sieve; 2,4,6-trichlorobenzoyl chloride; camphor-10-sulfonic acid; potassium tert-butylate; tetrabutyl ammonium fluoride; 3,3-dimethyldioxirane; tetra-(n-butyl)ammonium iodide; potassium hexamethylsilazane; zinc trifluoromethanesulfonate; 4-methylmorpholine N-oxide; triethylamine; 3-chloro-benzenecarboperoxoic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane; water; acetone; tert-butyl alcohol; 7.2: B-alkyl Suzuki coupling reaction;

DOI:10.1002/1521-3773(20010316)40:6<1090::AID-ANIE10900>3.0.CO;2-W

Reference yield:

Benzoic acid (1S,3S)-1-((R)-1,2-dihydroxy-ethyl)-3,7-dimethyl-oct-6-enyl ester (342901-76-2) → (2S,3R,5R,5aR,6aR,8R,10S,11R,12aS,13aR)-3,5-Bis-benzyloxy-2-(2-benzyloxy-ethyl)-5a-ethylsulfanyl-11-hydroxymethyl-8-methyl-tetradecahydro-1,6,12-trioxa-cyclohepta[4,5]benzo[1,2]cycloocten-10-ol

Guidance literature:

Multi-step reaction with 13 steps

1.1: 81 percent / KOH / methanol / 20 °C

2.1: 61 percent / camphorsulfonic acid / CH₂Cl₂ / 20 °C

3.1: OsO₄; N-methylmorpholine N-oxide / acetone; H₂O / 20 °C

3.2: 70 percent / NaIO₄ / acetone; H₂O

4.1: 95 percent / NaClO₂; KH₂PO₄; 2-methyl-2-butene / 2-methyl-propan-2-ol; H₂O / 20 °C

5.1: 2,4,6-trichlorobenzoyl chloride; Et₃N / tetrahydrofuran

5.2: 83 percent / DMAP / benzene / Heating

6.1: 95 percent / KHMDS / tetrahydrofuran; hexamethylphosphoric acid triamide / -78 °C

7.1: 9-BBN / tetrahydrofuran / 20 °C

7.2: 85 percent / 1 M aq. NaHCO₃ / [Pd(PPh₃)4] / dimethylformamide / 50 °C

8.1: 3,3-dimethyldioxirane / acetone / -78 - -20 °C

8.2: 60 percent / Et₃SiH; BH₃*THF / CH₂Cl₂ / -20 °C

9.1: 80 percent / t-BuOK; n-Bu₄NI / tetrahydrofuran / 20 °C

10.1: 97 percent / TBAF / tetrahydrofuran / 20 °C

11.1: 100 percent / tetrapropylammonium perruthenate; N-methylmorpholine N-oxide; 4 Angstroem molecular sieves / CH₂Cl₂ / 20 °C

12.1: DDQ / CH₂Cl₂; H₂O; various solvent(s) / 20 °C

13.1: Zn(OTf)2 / CH₂Cl₂ / 20 °C

With potassium hydroxide; sodium chlorite; potassium dihydrogenphosphate; osmium(VIII) oxide; 9-borabicyclo[3.3.1]nonane dimer; tetrapropylammonium perruthennate; 2-methyl-but-2-ene; 4 A molecular sieve; 2,4,6-trichlorobenzoyl chloride; camphor-10-sulfonic acid; potassium tert-butylate; tetrabutyl ammonium fluoride; 3,3-dimethyldioxirane; tetra-(n-butyl)ammonium iodide; potassium hexamethylsilazane; zinc trifluoromethanesulfonate; 4-methylmorpholine N-oxide; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane; water; acetone; tert-butyl alcohol; 7.2: B-alkyl Suzuki coupling reaction;

DOI:10.1002/1521-3773(20010316)40:6<1090::AID-ANIE10900>3.0.CO;2-W

upstream raw materials:

ammonium benzoate

Downstream raw materials:

(S)-5-((2R,4S,5R)-5-Hydroxy-2-phenyl-[1,3]dioxan-4-yl)-4-methyl-pentanal

(2R,4aR,9S,10aS)-9-Methyl-2-phenyl-hexahydro-1,3,5-trioxa-benzocycloocten-6-one

(S)-5-((2R,4S,5R)-5-Hydroxy-2-phenyl-[1,3]dioxan-4-yl)-4-methyl-pentanoic acid

(2R,4S,5R)-4-((S)-2,6-Dimethyl-hept-5-enyl)-2-phenyl-[1,3]dioxan-5-ol