(R)-2-[(4S,5S)-2-(4-methoxyphenyl)-5-methyl-1,3-dioxinan-4-yl]propionaldehyde

Base Information

• Chemical Name: (R)-2-[(4S,5S)-2-(4-methoxyphenyl)-5-methyl-1,3-dioxinan-4-yl]propionaldehyde
• CAS No.: 303727-85-7
• Molecular Formula: C₁₅H₂₀O₄
• Molecular Weight: 264.321

Synonyms:(R)-2-[(4S,5S)-2-(4-methoxyphenyl)-5-methyl-1,3-dioxinan-4-yl]propionaldehyde

Chemical Property of (R)-2-[(4S,5S)-2-(4-methoxyphenyl)-5-methyl-1,3-dioxinan-4-yl]propionaldehyde

Chemical Property:

Purity/Quality:

Safty Information:

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Useful:

Technology Process of (R)-2-[(4S,5S)-2-(4-methoxyphenyl)-5-methyl-1,3-dioxinan-4-yl]propionaldehyde

There total 2 articles about (R)-2-[(4S,5S)-2-(4-methoxyphenyl)-5-methyl-1,3-dioxinan-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:

(R)-N-methoxy-2-[(2S,4S,5S)-2-(4-methoxyphenyl)-5-methyl-1,3-dioxinan-4-yl]-N-methylpropionamide (303727-84-6) → (R)-2-[(4S,5S)-2-(4-methoxyphenyl)-5-methyl-1,3-dioxinan-4-yl]propionaldehyde (303727-85-7)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; at -60 - 0 ℃; for 3h;

DOI:10.1021/ja0015287

Reference yield:

(2'R,3'S,4'S,4R,5S)-3-[3'-hydroxy-5'-(4-methoxyphenyl)methoxy-2',4'-dimethylpentanoyl]-5-phenyl-4-methyl-2-oxazolidinone (132969-62-1) → (R)-2-[(4S,5S)-2-(4-methoxyphenyl)-5-methyl-1,3-dioxinan-4-yl]propionaldehyde (303727-85-7)

Guidance literature:

Multi-step reaction with 3 steps

1: Me₃Al / -78 °C

2: DDQ; 4 Angstroem MS

3: LAH / tetrahydrofuran

With lithium aluminium tetrahydride; 4 Angstroem MS; trimethylaluminum; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran;

DOI:10.1021/ol9910870

Reference yield: 96.0%

((S)-2-methyl-but-3-ynyloxymethyl)-benzene (934165-89-6) + (R)-2-[(4S,5S)-2-(4-methoxyphenyl)-5-methyl-1,3-dioxinan-4-yl]propionaldehyde (303727-85-7) → (2S,3S,6S)-7-benzyloxy-2-[(2S,4S,5S)-2-(4-methoxy-phenyl)-5-methyl-[1,3]dioxan-4-yl]-6-methyl-hept-4-yn-3-ol (944415-98-9)

Guidance literature:

With zinc trifluoromethanesulfonate; triethylamine; In toluene; at 20 ℃; for 24h;

DOI:10.1016/j.tet.2007.01.067

upstream raw materials:

(R)-N-methoxy-2-[(2S,4S,5S)-2-(4-methoxyphenyl)-5-methyl-1,3-dioxinan-4-yl]-N-methylpropionamide

(2'R,3'S,4'S,4R,5S)-3-[3'-hydroxy-5'-(4-methoxyphenyl)methoxy-2',4'-dimethylpentanoyl]-5-phenyl-4-methyl-2-oxazolidinone

Downstream raw materials:

(R)-4-Benzyl-3-{(2R,3S,4S)-3-hydroxy-4-[(2S,4S,5S)-2-(4-methoxy-phenyl)-5-methyl-[1,3]dioxan-4-yl]-2-methyl-pentanoyl}-oxazolidin-2-one

(2S,3S,6S)-7-benzyloxy-2-[(2S,4S,5S)-2-(4-methoxy-phenyl)-5-methyl-[1,3]dioxan-4-yl]-6-methyl-hept-4-yn-3-ol

(2S,3R,4R)-3-(tert-Butyl-dimethyl-silanyloxy)-4-[(2S,4S,5S)-2-(4-methoxy-phenyl)-5-methyl-[1,3]dioxan-4-yl]-2-methyl-pentan-1-ol

tert-Butyl-((1S,2R)-3-iodo-1-{(R)-1-[(2S,4S,5S)-2-(4-methoxy-phenyl)-5-methyl-[1,3]dioxan-4-yl]-ethyl}-2-methyl-propoxy)-dimethyl-silane

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