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

Base Information

• Chemical Name: Octanoic acid, 6,8-bis(phenylmethoxy)-, (S)-
• CAS No.: 116315-78-7
• Molecular Formula: C22H28O4
• Molecular Weight: 356.462
• Mol file: 116315-78-7.mol

Synonyms:

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 10 articles about Octanoic acid, 6,8-bis(phenylmethoxy)-, (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)-6,8-diphenylmethoxyoctanoic acid (116315-78-7)

Guidance literature:

Multi-step reaction with 5 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

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; 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)-6,8-diphenylmethoxyoctanoic acid (116315-78-7)

Guidance literature:

Multi-step reaction with 4 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

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; 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)-6,8-diphenylmethoxyoctanoic acid (116315-78-7)

Guidance literature:

Multi-step reaction with 5 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

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

DOI:10.1039/P19880000009

upstream raw materials:

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

benzyl bromide

4-benzyloxybut-1-ene

2-(2-(benzyloxy)ethyl)oxirane

Downstream raw materials:

(S)-methyl 6,8-diphenylmethoxyoctanoate

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

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