2-{(4S,5S)-5-Benzyloxymethyl-4-[2-(4-methoxy-benzyloxy)-ethyl]-2-oxo-cyclohexyl}-malonic acid diethyl ester

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Chemical Name:2-{(4S,5S)-5-Benzyloxymethyl-4-[2-(4-methoxy-benzyloxy)-ethyl]-2-oxo-cyclohexyl}-malonic acid diethyl ester
CAS No.:565436-07-9
Molecular Formula:C₃₁H₄₀O₈
Molecular Weight:540.654
Hs Code.:

Synonyms:2-{(4S,5S)-5-Benzyloxymethyl-4-[2-(4-methoxy-benzyloxy)-ethyl]-2-oxo-cyclohexyl}-malonic acid diethyl ester

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Chemical Property of 2-{(4S,5S)-5-Benzyloxymethyl-4-[2-(4-methoxy-benzyloxy)-ethyl]-2-oxo-cyclohexyl}-malonic acid diethyl ester

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Technology Process of 2-{(4S,5S)-5-Benzyloxymethyl-4-[2-(4-methoxy-benzyloxy)-ethyl]-2-oxo-cyclohexyl}-malonic acid diethyl ester

There total 5 articles about 2-{(4S,5S)-5-Benzyloxymethyl-4-[2-(4-methoxy-benzyloxy)-ethyl]-2-oxo-cyclohexyl}-malonic acid diethyl ester 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: 73.0%

: 541-41-3
chloroformic acid ethyl ester

: 566163-71-1
(3S,4S)-4-Benzyloxymethyl-1-(tert-butyl-dimethyl-silanyloxy)-3-[2-(4-methoxy-benzyloxy)-ethyl]-bicyclo[4.1.0]heptane-7-carboxylic acid ethyl ester

: 565436-07-9
2-{(4S,5S)-5-Benzyloxymethyl-4-[2-(4-methoxy-benzyloxy)-ethyl]-2-oxo-cyclohexyl}-malonic acid diethyl ester

Guidance literature:: (3S,4S)-4-Benzyloxymethyl-1-(tert-butyl-dimethyl-silanyloxy)-3-[2-(4-methoxy-benzyloxy)-ethyl]-bicyclo[4.1.0]heptane-7-carboxylic acid ethyl ester; With lithium diisopropyl amide; In tetrahydrofuran; at -78 ℃; for 0.5h;

chloroformic acid ethyl ester; In tetrahydrofuran; at -78 - 20 ℃; for 12h;

With tetrabutyl ammonium fluoride; In tetrahydrofuran;
DOI:10.1016/S0040-4039(03)00835-9

Reference yield:

: (S)-4-Benzyl-3-[(E)-5-(4-methoxy-benzyloxy)-pent-2-enoyl]-oxazolidin-2-one

: 565436-07-9
2-{(4S,5S)-5-Benzyloxymethyl-4-[2-(4-methoxy-benzyloxy)-ethyl]-2-oxo-cyclohexyl}-malonic acid diethyl ester

Guidance literature:: Multi-step reaction with 5 steps

1.1: 81 percent / Et₂AlCl / CH₂Cl₂ / -78 - -20 °C

2.1: 51 percent / LiBH₄; EtOH / tetrahydrofuran / 0 - 20 °C

3.1: 60 percent / NaH; nBu₄NBr / tetrahydrofuran

4.1: 96 percent / Cu(acac)2 / ethyl acetate / 110 °C

5.1: LDA / tetrahydrofuran / 0.5 h / -78 °C

5.2: tetrahydrofuran / 12 h / -78 - 20 °C

5.3: 73 percent / TBAF / tetrahydrofuran

With lithium borohydride; ethanol; tetrabutylammomium bromide; diethylaluminium chloride; sodium hydride; lithium diisopropyl amide; copper acetylacetonate; In tetrahydrofuran; dichloromethane; ethyl acetate; 1.1: Diels-Alder reaction;
DOI:10.1016/S0040-4039(03)00835-9

Reference yield:

: {(1S,6S)-4-(tert-Butyl-dimethyl-silanyloxy)-6-[2-(4-methoxy-benzyloxy)-ethyl]-cyclohex-3-enyl}-methanol

: 565436-07-9
2-{(4S,5S)-5-Benzyloxymethyl-4-[2-(4-methoxy-benzyloxy)-ethyl]-2-oxo-cyclohexyl}-malonic acid diethyl ester

Guidance literature:: Multi-step reaction with 3 steps

1.1: 60 percent / NaH; nBu₄NBr / tetrahydrofuran

2.1: 96 percent / Cu(acac)2 / ethyl acetate / 110 °C

3.1: LDA / tetrahydrofuran / 0.5 h / -78 °C

3.2: tetrahydrofuran / 12 h / -78 - 20 °C

3.3: 73 percent / TBAF / tetrahydrofuran

With tetrabutylammomium bromide; sodium hydride; lithium diisopropyl amide; copper acetylacetonate; In tetrahydrofuran; ethyl acetate;
DOI:10.1016/S0040-4039(03)00835-9