(3S,5S,6S)-[(S)-1-hydroxy-3-methylbutyl]-5,6-bis-(4-methoxyphenyl)-1,4-dioxan-2-one

Base Information

• Chemical Name: (3S,5S,6S)-[(S)-1-hydroxy-3-methylbutyl]-5,6-bis-(4-methoxyphenyl)-1,4-dioxan-2-one
• CAS No.: 448293-78-5
• Molecular Formula: C₂₃H₂₈O₆
• Molecular Weight: 400.472
• Mol file: 448293-78-5.mol

Synonyms:(3S,5S,6S)-[(S)-1-hydroxy-3-methylbutyl]-5,6-bis-(4-methoxyphenyl)-1,4-dioxan-2-one

Chemical Property of (3S,5S,6S)-[(S)-1-hydroxy-3-methylbutyl]-5,6-bis-(4-methoxyphenyl)-1,4-dioxan-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S,5S,6S)-[(S)-1-hydroxy-3-methylbutyl]-5,6-bis-(4-methoxyphenyl)-1,4-dioxan-2-one

There total 5 articles about (3S,5S,6S)-[(S)-1-hydroxy-3-methylbutyl]-5,6-bis-(4-methoxyphenyl)-1,4-dioxan-2-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: 86.0%

isovaleraldehyde (590-86-3) + (S,S)-5,6-bis-(4-methoxyphenyl)-[1,4]-dioxan-2-one (326606-11-5) → (3R,5S,6S)-[(R)-1-hydroxy-3-methylbutyl]-5,6-bis-(4-methoxyphenyl)-1,4-dioxan-2-one + (3R,5S,6S)-3-((S)-1-Hydroxy-3-methyl-butyl)-5,6-bis-(4-methoxy-phenyl)-[1,4]dioxan-2-one + (3S,5S,6S)-3-((R)-1-Hydroxy-3-methyl-butyl)-5,6-bis-(4-methoxy-phenyl)-[1,4]dioxan-2-one + (3S,5S,6S)-[(S)-1-hydroxy-3-methylbutyl]-5,6-bis-(4-methoxyphenyl)-1,4-dioxan-2-one (448293-78-5)

Guidance literature:

(S,S)-5,6-bis-(4-methoxyphenyl)-[1,4]-dioxan-2-one; With triethylamine; dicyclohexyl(((trifluoromethyl)sulfonyl)oxy)borane; In hexane; dichloromethane; at -78 ℃; for 3h;

isovaleraldehyde; In hexane; dichloromethane; for 0.5h;

DOI:10.1016/S0040-4039(02)00152-1

Reference yield:

1,2-bis(4-methoxyphenyl)ethene (4705-34-4,15638-14-9,34480-01-8,112246-67-0,2510-75-0) → (3S,5S,6S)-[(S)-1-hydroxy-3-methylbutyl]-5,6-bis-(4-methoxyphenyl)-1,4-dioxan-2-one (448293-78-5)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 84 percent / AD-mix-α / 2-methyl-propan-2-ol; H2O

2.1: n-Bu₂SnO; Bu₄NI / benzene / Heating

2.2: 81 percent / benzene

3.1: Et₃N; c-Hex₂BOTf / CH₂Cl₂; hexane / 3 h / -78 °C

3.2: 86 percent / CH₂Cl₂; hexane / 0.5 h

With AD-mix-α; tetra-(n-butyl)ammonium iodide; di(n-butyl)tin oxide; triethylamine; dicyclohexyl(((trifluoromethyl)sulfonyl)oxy)borane; In hexane; dichloromethane; water; tert-butyl alcohol; benzene;

DOI:10.1016/S0040-4039(02)00152-1

Reference yield:

diethyl 4-methoxybenzylphosphonate (1145-93-3) → (3S,5S,6S)-[(S)-1-hydroxy-3-methylbutyl]-5,6-bis-(4-methoxyphenyl)-1,4-dioxan-2-one (448293-78-5)

Guidance literature:

Multi-step reaction with 4 steps

1.1: NaOMe / dimethylformamide / 0.33 h / 20 °C

1.2: 93 percent / dimethylformamide / 7 h / 100 °C

2.1: 84 percent / AD-mix-α / 2-methyl-propan-2-ol; H2O

3.1: n-Bu₂SnO; Bu₄NI / benzene / Heating

3.2: 81 percent / benzene

4.1: Et₃N; c-Hex₂BOTf / CH₂Cl₂; hexane / 3 h / -78 °C

4.2: 86 percent / CH₂Cl₂; hexane / 0.5 h

With AD-mix-α; sodium methylate; tetra-(n-butyl)ammonium iodide; di(n-butyl)tin oxide; triethylamine; dicyclohexyl(((trifluoromethyl)sulfonyl)oxy)borane; In hexane; dichloromethane; water; N,N-dimethyl-formamide; tert-butyl alcohol; benzene;

DOI:10.1016/S0040-4039(02)00152-1

upstream raw materials:

isovaleraldehyde

(S,S)-5,6-bis-(4-methoxyphenyl)-[1,4]-dioxan-2-one

1,2-bis(4-methoxyphenyl)ethene

diethyl 4-methoxybenzylphosphonate

Downstream raw materials:

(3S,5S,6S)-3-((S)-1-Methoxy-3-methyl-butyl)-5,6-bis-(4-methoxy-phenyl)-[1,4]dioxan-2-one

(2S,3S)-2-[(1S,2S)-2-Hydroxy-1,2-bis-(4-methoxy-phenyl)-ethoxy]-3-methoxy-5-methyl-hexanoic acid methyl ester