(S)-3-(4-Methoxy-benzyloxy)-4,4-dimethyl-6,6-diphenyl-hex-5-enal

Base Information

• Chemical Name: (S)-3-(4-Methoxy-benzyloxy)-4,4-dimethyl-6,6-diphenyl-hex-5-enal
• CAS No.: 215876-04-3
• Molecular Formula: C₂₈H₃₀O₃
• Molecular Weight: 414.544
• Mol file: 215876-04-3.mol

Synonyms:(S)-3-(4-Methoxy-benzyloxy)-4,4-dimethyl-6,6-diphenyl-hex-5-enal

Chemical Property of (S)-3-(4-Methoxy-benzyloxy)-4,4-dimethyl-6,6-diphenyl-hex-5-enal

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-3-(4-Methoxy-benzyloxy)-4,4-dimethyl-6,6-diphenyl-hex-5-enal

There total 6 articles about (S)-3-(4-Methoxy-benzyloxy)-4,4-dimethyl-6,6-diphenyl-hex-5-enal 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: 96.0%

(S)-3-(4-Methoxy-benzyloxy)-4,4-dimethyl-6,6-diphenyl-hex-5-en-1-ol (247146-14-1) → (S)-3-(4-Methoxy-benzyloxy)-4,4-dimethyl-6,6-diphenyl-hex-5-enal (215876-04-3)

Guidance literature:

With oxalyl dichloride; dimethyl sulfoxide; triethylamine; In dichloromethane; at -78 ℃;

DOI:10.1021/ja990860j

Reference yield:

2,2-dimethyl-4,4-diphenyl-but-3-enal (5820-02-0) → (S)-3-(4-Methoxy-benzyloxy)-4,4-dimethyl-6,6-diphenyl-hex-5-enal (215876-04-3)

Guidance literature:

Multi-step reaction with 6 steps

1: Bu₂BOTf; i-Pr₂NEt / CH₂Cl₂ / 20 h / -78 - 0 °C

2: Zn; AcOH / tetrahydrofuran

3: 67 percent / LiBH₄ / methanol; tetrahydrofuran / 0 °C

4: PPTS / CH₂Cl₂

5: 94 percent / DIBAL-H / CH₂Cl₂ / 0 °C

6: 96 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 °C

With lithium borohydride; oxalyl dichloride; di-n-butylboryl trifluoromethanesulfonate; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; acetic acid; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; zinc; In tetrahydrofuran; methanol; dichloromethane; 1: Condensation / 2: Dehalogenation / 3: Reduction / 4: acetalization / 5: reductive cleavage / 6: Oxidation;

DOI:10.1021/ja990860j

Reference yield:

(S)-4,4-Dimethyl-6,6-diphenyl-hex-5-ene-1,3-diol (247146-13-0) → (S)-3-(4-Methoxy-benzyloxy)-4,4-dimethyl-6,6-diphenyl-hex-5-enal (215876-04-3)

Guidance literature:

Multi-step reaction with 3 steps

1: PPTS / CH₂Cl₂

2: 94 percent / DIBAL-H / CH₂Cl₂ / 0 °C

3: 96 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 °C

With oxalyl dichloride; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; In dichloromethane; 1: acetalization / 2: reductive cleavage / 3: Oxidation;

DOI:10.1021/ja990860j

upstream raw materials:

(S)-3-(4-Methoxy-benzyloxy)-4,4-dimethyl-6,6-diphenyl-hex-5-en-1-ol

2,2-dimethyl-4,4-diphenyl-but-3-enal

(S)-4,4-Dimethyl-6,6-diphenyl-hex-5-ene-1,3-diol

(S)-4-Benzyl-3-((S)-3-hydroxy-4,4-dimethyl-6,6-diphenyl-hex-5-enoyl)-oxazolidin-2-one

Downstream raw materials:

(R)-4-[(2S,4S,6R)-6-Benzenesulfonyl-4-(4-methoxy-benzyloxy)-5,5-dimethyl-tetrahydro-pyran-2-yl]-3-(tert-butyl-dimethyl-silanyloxy)-N-phenyl-butyramide

(4R,6R)-4-Hydroxy-6-[(S)-2-(4-methoxy-benzyloxy)-3,3-dimethyl-5,5-diphenyl-pent-4-enyl]-tetrahydro-pyran-2-one

(R)-4-((2S,4S)-4-(4-methoxybenzyloxy)-6-hydroxy-5,5-dimethyl-tetrahydro-2H-pyran-2-yl)-3-(tert-butyldimethylsilyloxy)-N-phenylbutanamide

(4R,6S)-4-(tert-Butyl-dimethyl-silanyloxy)-6-[(S)-2-(4-methoxy-benzyloxy)-3,3-dimethyl-5,5-diphenyl-pent-4-enyl]-tetrahydro-pyran-2-one