(2R,5S)-5-hydroxy-2-[(2S,4S,5S)-2-(4-methoxyphenyl)-5-methyl-1,3-dioxan-4-yl]-4,4-dimethyloct-7-en-3-one

Base Information

• Chemical Name: (2R,5S)-5-hydroxy-2-[(2S,4S,5S)-2-(4-methoxyphenyl)-5-methyl-1,3-dioxan-4-yl]-4,4-dimethyloct-7-en-3-one
• CAS No.: 186417-90-3
• Molecular Formula: C₂₂H₃₂O₅
• Molecular Weight: 376.493

Synonyms:(2R,5S)-5-hydroxy-2-[(2S,4S,5S)-2-(4-methoxyphenyl)-5-methyl-1,3-dioxan-4-yl]-4,4-dimethyloct-7-en-3-one

Chemical Property of (2R,5S)-5-hydroxy-2-[(2S,4S,5S)-2-(4-methoxyphenyl)-5-methyl-1,3-dioxan-4-yl]-4,4-dimethyloct-7-en-3-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

Useful:

Technology Process of (2R,5S)-5-hydroxy-2-[(2S,4S,5S)-2-(4-methoxyphenyl)-5-methyl-1,3-dioxan-4-yl]-4,4-dimethyloct-7-en-3-one

There total 10 articles about (2R,5S)-5-hydroxy-2-[(2S,4S,5S)-2-(4-methoxyphenyl)-5-methyl-1,3-dioxan-4-yl]-4,4-dimethyloct-7-en-3-one 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)-4-[(2S,4S,5S)-2-(4-Methoxy-phenyl)-5-methyl-[1,3]dioxan-4-yl]-2,2-dimethyl-3-oxo-pentanal (186417-89-0) + allylmagnesium bromide (1730-25-2) → (+)-(2R,5R)-5-hydroxy-2-[(2S,4S,5S)-2-(4-methoxyphenyl)-5-methyl-1,3-dioxan-4-yl]-4,4-dimethyloct-7-en-3-one + (2R,5S)-5-hydroxy-2-[(2S,4S,5S)-2-(4-methoxyphenyl)-5-methyl-1,3-dioxan-4-yl]-4,4-dimethyloct-7-en-3-one (186417-90-3)

Guidance literature:

allylmagnesium bromide; With (-)-diisopinocamphenylborane chloride; In diethyl ether; at -78 ℃; for 0.5h;

(R)-4-[(2S,4S,5S)-2-(4-Methoxy-phenyl)-5-methyl-[1,3]dioxan-4-yl]-2,2-dimethyl-3-oxo-pentanal; In tetrahydrofuran; diethyl ether; at -78 ℃; for 3h; Further stages.;

DOI:10.1021/jo0007480

Reference yield:

3,3-dimethyl-4-oxohex-1-ene (78186-80-8) → (2R,5S)-5-hydroxy-2-[(2S,4S,5S)-2-(4-methoxyphenyl)-5-methyl-1,3-dioxan-4-yl]-4,4-dimethyloct-7-en-3-one (186417-90-3)

Guidance literature:

Multi-step reaction with 4 steps

1.1: LDA / tetrahydrofuran; various solvent(s) / 0.5 h / -90 °C

1.2: tetrahydrofuran; various solvent(s) / 0.17 h / -90 °C

2.1: 86 percent / DDQ; molecular sieves 4 Angstroem / CH₂Cl₂ / 3 h / -15 - 0 °C

3.1: O₃ / CH₂Cl₂; methanol / -78 °C

3.2: 93 percent / Me₂S / CH₂Cl₂; methanol / -78 - 20 °C

4.1: (-)DIPCl / diethyl ether / 0.5 h / -78 °C

4.2: diethyl ether; tetrahydrofuran / 3 h / -78 °C

With 4 A molecular sieve; ozone; (-)-diisopinocamphenylborane chloride; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium diisopropyl amide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; 4.2: Brown allylation;

DOI:10.1021/jo0007480

Reference yield:

(2S)-3-[(4-methoxybenzyl)oxy]-2-methylpropanal (132969-60-9) → (2R,5S)-5-hydroxy-2-[(2S,4S,5S)-2-(4-methoxyphenyl)-5-methyl-1,3-dioxan-4-yl]-4,4-dimethyloct-7-en-3-one (186417-90-3)

Guidance literature:

Multi-step reaction with 4 steps

1.1: LDA / tetrahydrofuran; various solvent(s) / 0.5 h / -90 °C

1.2: tetrahydrofuran; various solvent(s) / 0.17 h / -90 °C

2.1: 86 percent / DDQ; molecular sieves 4 Angstroem / CH₂Cl₂ / 3 h / -15 - 0 °C

3.1: O₃ / CH₂Cl₂; methanol / -78 °C

3.2: 93 percent / Me₂S / CH₂Cl₂; methanol / -78 - 20 °C

4.1: (-)DIPCl / diethyl ether / 0.5 h / -78 °C

4.2: diethyl ether; tetrahydrofuran / 3 h / -78 °C

With 4 A molecular sieve; ozone; (-)-diisopinocamphenylborane chloride; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium diisopropyl amide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; 4.2: Brown allylation;

DOI:10.1021/jo0007480

upstream raw materials:

B-allyldiisopinocampheylborane

(R)-4-[(2S,4S,5S)-2-(4-Methoxy-phenyl)-5-methyl-[1,3]dioxan-4-yl]-2,2-dimethyl-3-oxo-pentanal

allylmagnesium bromide

3,3-dimethyl-4-oxohex-1-ene

Downstream raw materials:

(2S,3S,4R,7S)-7-(tert-Butyl-dimethyl-silanyloxy)-3-hydroxy-1-(4-methoxy-benzyloxy)-2,4,6,6-tetramethyl-dec-9-en-5-one

(-)-(2R,5S)-5-{[tert-butyl(dimethyl)silyl]oxy}-2-[(2S,4S,5S)-2-(4-methoxyphenyl)-5-methyl-1,3-dioxan-4-yl]-4,4-dimethyloct-7-en-3-one

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