(S)-2-[(2S,4S,5S)-2-(4-Methoxy-phenyl)-5-methyl-[1,3]dioxan-4-yl]-propionaldehyde

Base Information

• Chemical Name: (S)-2-[(2S,4S,5S)-2-(4-Methoxy-phenyl)-5-methyl-[1,3]dioxan-4-yl]-propionaldehyde
• CAS No.: 845780-55-4
• Molecular Formula: C₁₅H₂₀O₄
• Molecular Weight: 264.321
• Mol file: 845780-55-4.mol

Synonyms:(S)-2-[(2S,4S,5S)-2-(4-Methoxy-phenyl)-5-methyl-[1,3]dioxan-4-yl]-propionaldehyde

Chemical Property of (S)-2-[(2S,4S,5S)-2-(4-Methoxy-phenyl)-5-methyl-[1,3]dioxan-4-yl]-propionaldehyde

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-2-[(2S,4S,5S)-2-(4-Methoxy-phenyl)-5-methyl-[1,3]dioxan-4-yl]-propionaldehyde

There total 1 articles about (S)-2-[(2S,4S,5S)-2-(4-Methoxy-phenyl)-5-methyl-[1,3]dioxan-4-yl]-propionaldehyde 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:

(2R)-2-[(2S,4R,5S)-2-(4-methoxyphenyl)-5-methyl-1,3-dioxan-4-yl]propan-1-ol (845780-29-2) → (S)-2-[(2S,4S,5S)-2-(4-Methoxy-phenyl)-5-methyl-[1,3]dioxan-4-yl]-propionaldehyde (845780-55-4)

Guidance literature:

With Dess-Martin periodane; In dichloromethane;

DOI:10.1021/ol0478279

Reference yield: 83.0%

(3R)-3-propionyl-4-benzyloxazolidin-2-one (101711-78-8,131685-53-5) + (S)-2-[(2S,4S,5S)-2-(4-Methoxy-phenyl)-5-methyl-[1,3]dioxan-4-yl]-propionaldehyde (845780-55-4) → (4R)-4-benzyl-3-{(2R,3S,4R)-3-hydroxy-4-[(2S,4S,5S)-2-(4-methoxyphenyl)-5-methyl[1,3]dioxan-4-yl]-2-methylpentanoyl}-oxazolidin-2-one (845780-42-9)

Guidance literature:

With di-n-butylboryl trifluoromethanesulfonate; triethylamine; In dichloromethane; at -78 ℃; for 1.5h;

DOI:10.1021/ol0478279

Reference yield:

(S)-2-[(2S,4S,5S)-2-(4-Methoxy-phenyl)-5-methyl-[1,3]dioxan-4-yl]-propionaldehyde (845780-55-4) → (2R,4R)-4-[(2S,4R,5S)-2-(4-Methoxy-phenyl)-5-methyl-[1,3]dioxan-4-yl]-2-methyl-pentanal

Guidance literature:

Multi-step reaction with 5 steps

1: 83 percent / n-Bu₂BOTf; Et₃N / CH₂Cl₂ / 1.5 h / -78 °C

2: 89 percent / lithium borohydride / methanol; diethyl ether / 2.5 h / 0 - 20 °C

3: 79 percent / DMAP / tetrahydrofuran / 2.5 h / 20 - 60 °C

4: 75 percent / Bu₃SnH; AIBN / toluene / 2 h / Heating

5: NMO; molecular sieves 4 Angstroem; TPAP / CH₂Cl₂ / 2 h / 20 °C

With dmap; lithium borohydride; N-methyl-2-indolinone; tetrapropylammonium perruthennate; 2,2'-azobis(isobutyronitrile); 4 A molecular sieve; di-n-butylboryl trifluoromethanesulfonate; tri-n-butyl-tin hydride; triethylamine; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; toluene; 4: Barton-McCombie deoxygenation;

DOI:10.1021/ol0478279

upstream raw materials:

(2R)-2-[(2S,4R,5S)-2-(4-methoxyphenyl)-5-methyl-1,3-dioxan-4-yl]propan-1-ol

Downstream raw materials:

(4R)-4-benzyl-3-{(2R,3S,4R)-3-hydroxy-4-[(2S,4S,5S)-2-(4-methoxyphenyl)-5-methyl[1,3]dioxan-4-yl]-2-methylpentanoyl}-oxazolidin-2-one

(2R,4R)-4-[(2S,4S,5S)-2-(4-methoxyphenyl)-5-methyl[1,3]dioxan-4-yl]-2-methylpentan-1-ol

(2R,3R,4R)-4-[(2S,4S,5S)-2-(4-methoxyphenyl)-5-methyl[1,3]dioxan-4-yl]-2-methylpentane-1,3-diol

(4R,5S)-4-{(1S)-1-[(2S,4S,5S)-2-(4-methoxyphenyl)-5-methyl[1,3]dioxan-4-yl]ethyl}-5-methyl[1,3]dioxane-2-thione