ethyl 2-(1S,4S,5R)-1,5-di[(methoxymethoxy)methyl]-4,5-dimethyl-6-oxo-2-cyclohexenylacetate

Base Information

Chemical Name:ethyl 2-(1S,4S,5R)-1,5-di[(methoxymethoxy)methyl]-4,5-dimethyl-6-oxo-2-cyclohexenylacetate
CAS No.:1395878-49-5
Molecular Formula:C₁₈H₃₀O₇
Molecular Weight:358.432
Hs Code.:

Synonyms:ethyl 2-(1S,4S,5R)-1,5-di[(methoxymethoxy)methyl]-4,5-dimethyl-6-oxo-2-cyclohexenylacetate

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Chemical Property of ethyl 2-(1S,4S,5R)-1,5-di[(methoxymethoxy)methyl]-4,5-dimethyl-6-oxo-2-cyclohexenylacetate

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Technology Process of ethyl 2-(1S,4S,5R)-1,5-di[(methoxymethoxy)methyl]-4,5-dimethyl-6-oxo-2-cyclohexenylacetate

There total 6 articles about ethyl 2-(1S,4S,5R)-1,5-di[(methoxymethoxy)methyl]-4,5-dimethyl-6-oxo-2-cyclohexenylacetate 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: 27.0%

: 1395878-47-3
(4R,5R,6R)-4-hydroxy-2,6-di[(methoxymethoxy)methyl]-5,6-dimethyl-2-cyclohexen-1-one

: 78-39-7
Triethyl orthoacetate

: 1395878-48-4
(6R)-2,6-di[(methoxymethoxy)methyl]-5,6-dimethyl-2,4-cyclohexadien-1-one

: 1395878-49-5
ethyl 2-(1S,4S,5R)-1,5-di[(methoxymethoxy)methyl]-4,5-dimethyl-6-oxo-2-cyclohexenylacetate

Guidance literature:: With propionic acid; Overall yield = 97 %; stereoselective reaction; Sealed tube; Inert atmosphere; Heating;
DOI:10.1021/jo301258g

Reference yield:

: 1395878-42-8
(2S,5R,6S,7R)-6-[1-(tert-butyl)-1,1-dimethylsilyl]oxy-5-methyltricyclo[6.2.1.0^2,7]undec-9-en-3-one

: 1395878-49-5
ethyl 2-(1S,4S,5R)-1,5-di[(methoxymethoxy)methyl]-4,5-dimethyl-6-oxo-2-cyclohexenylacetate

Guidance literature:: Multi-step reaction with 6 steps

1.1: lithium hexamethyldisilazane / tetrahydrofuran / 1.25 h / -78 - -20 °C / Inert atmosphere

1.2: 1 h / -78 - 0 °C / Inert atmosphere

2.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran; water / 12 h / 25 °C / Cooling with ice

3.1: dmap; N-ethyl-N,N-diisopropylamine / dichloromethane / 6 h / 25 °C / Cooling with ice

4.1: diphenylether / 0.25 h / Heating; Inert atmosphere

5.1: tetrabutyl ammonium fluoride; acetic acid / tetrahydrofuran / 10 h / 25 °C / Inert atmosphere

6.1: propionic acid / Sealed tube; Inert atmosphere; Heating

With dmap; tetrabutyl ammonium fluoride; acetic acid; propionic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; N-ethyl-N,N-diisopropylamine; lithium hexamethyldisilazane; In tetrahydrofuran; diphenylether; dichloromethane; water; 6.1: |Johnson-Claisen Rearrangement;
DOI:10.1021/jo301258g

Reference yield:

: 1395878-43-9
(2S,4S,5R,6S,7R)-6-[1-(tert-butyl)-1,1-dimethylsilyl]oxy-4,5-dimethyltricyclo[6.2.1.0^2,7]undec-9-en-3-one

: 1395878-49-5
ethyl 2-(1S,4S,5R)-1,5-di[(methoxymethoxy)methyl]-4,5-dimethyl-6-oxo-2-cyclohexenylacetate

Guidance literature:: Multi-step reaction with 5 steps

1: 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran; water / 12 h / 25 °C / Cooling with ice

2: dmap; N-ethyl-N,N-diisopropylamine / dichloromethane / 6 h / 25 °C / Cooling with ice

3: diphenylether / 0.25 h / Heating; Inert atmosphere

4: tetrabutyl ammonium fluoride; acetic acid / tetrahydrofuran / 10 h / 25 °C / Inert atmosphere

5: propionic acid / Sealed tube; Inert atmosphere; Heating

With dmap; tetrabutyl ammonium fluoride; acetic acid; propionic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; diphenylether; dichloromethane; water; 5: |Johnson-Claisen Rearrangement;
DOI:10.1021/jo301258g