Octanoic acid, 6,8-bis(phenylmethoxy)-, methyl ester, (S)-

Base Information

• Chemical Name: Octanoic acid, 6,8-bis(phenylmethoxy)-, methyl ester, (S)-
• CAS No.: 116315-79-8
• Molecular Formula: C23H30O4
• Molecular Weight: 370.489
• Mol file: 116315-79-8.mol

Synonyms:

Chemical Property of Octanoic acid, 6,8-bis(phenylmethoxy)-, methyl ester, (S)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Octanoic acid, 6,8-bis(phenylmethoxy)-, methyl ester, (S)-

There total 13 articles about Octanoic acid, 6,8-bis(phenylmethoxy)-, methyl ester, (S)- 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:

(S)-4-benzyloxy-1,2-butanediol (71998-69-1,86990-91-2,104973-80-0,69985-32-6) → (S)-methyl 6,8-diphenylmethoxyoctanoate (116315-79-8)

Guidance literature:

Multi-step reaction with 6 steps

1.1: Ph₃P; DIAD / benzene / 20 h / Heating

2.1: Mg; CH₂BrCH₂Br / tetrahydrofuran / 1 h / 20 °C

2.2: LiCuCl₄ / tetrahydrofuran / 1 h / -78 °C

2.3: 90 percent / tetrahydrofuran / -78 - 20 °C

3.1: 85 percent / TBAI; NaH / dimethylformamide / 2 h / 20 °C

4.1: BH₃*DMS / tetrahydrofuran / 2 h / 20 °C

4.2: 88 percent / aq. NaOEt; H₂O₂ / tetrahydrofuran / 2 h / 20 °C

5.1: aq. NaCl₂O; NaOCl; TEMPO / acetonitrile; aq. phosphate buffer / 35 °C / pH 6.7

6.1: 1.75 g / diethyl ether

With 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hypochlorite; di-isopropyl azodicarboxylate; dimethylsulfide borane complex; tetra-(n-butyl)ammonium iodide; sodium hydride; magnesium; ethylene dibromide; triphenylphosphine; In tetrahydrofuran; phosphate buffer; diethyl ether; N,N-dimethyl-formamide; acetonitrile; benzene; 1.1: Mitsunobu reaction;

DOI:10.1055/s-2006-942363

Reference yield:

(2R)-2-(2-benzyloxyethyl)oxirane (115114-87-9) → (S)-methyl 6,8-diphenylmethoxyoctanoate (116315-79-8)

Guidance literature:

Multi-step reaction with 5 steps

1.1: Mg; CH₂BrCH₂Br / tetrahydrofuran / 1 h / 20 °C

1.2: LiCuCl₄ / tetrahydrofuran / 1 h / -78 °C

1.3: 90 percent / tetrahydrofuran / -78 - 20 °C

2.1: 85 percent / TBAI; NaH / dimethylformamide / 2 h / 20 °C

3.1: BH₃*DMS / tetrahydrofuran / 2 h / 20 °C

3.2: 88 percent / aq. NaOEt; H₂O₂ / tetrahydrofuran / 2 h / 20 °C

4.1: aq. NaCl₂O; NaOCl; TEMPO / acetonitrile; aq. phosphate buffer / 35 °C / pH 6.7

5.1: 1.75 g / diethyl ether

With 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hypochlorite; dimethylsulfide borane complex; tetra-(n-butyl)ammonium iodide; sodium hydride; magnesium; ethylene dibromide; In tetrahydrofuran; phosphate buffer; diethyl ether; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1055/s-2006-942363

Reference yield:

(R)-4-phenylmethoxy-1,2-butanediol (69985-32-6,71998-69-1,104973-80-0,86990-91-2) → (S)-methyl 6,8-diphenylmethoxyoctanoate (116315-79-8)

Guidance literature:

Multi-step reaction with 6 steps

2: 1.) Mg, 1,2-dibromoethane / 2.) Li₂CuCl₄ / 1.) THF, reflux, 2.) THF, -78 deg C, 5 h, then RT

3: 95 percent

4: 89 percent / diisopentylborane / tetrahydrofuran / 0 °C

5: pyridinium dichromate / dimethylformamide / 0 deg C, then RT, 24 h

6: 3percent HCl

With hydrogenchloride; dipyridinium dichromate; diisoamyl borane; magnesium; ethylene dibromide; dilithium tetrachlorocuprate; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1039/P19880000009

upstream raw materials:

methanol

(S)-6,8-diphenylmethoxyoctanoic acid

diazomethane

(S)-4-benzyloxy-1,2-butanediol

Downstream raw materials:

(6S)-(-)-methyl 6,8-dihydroxyoctanoate

(R)-1,2-dithiolane-3-pentanoic acid