methyl (1'R,4'S)-2-(4'-benzoyloxy-2'-cyclohexen-1'-yl)-2-N-[6''-bromo-3'',4''-(methylene-dioxy)benzyl]carbamoylacetate

Base Information

Chemical Name:methyl (1'R,4'S)-2-(4'-benzoyloxy-2'-cyclohexen-1'-yl)-2-N-[6''-bromo-3'',4''-(methylene-dioxy)benzyl]carbamoylacetate
CAS No.:888316-54-9
Molecular Formula:C₂₅H₂₄BrNO₇
Molecular Weight:530.372
Hs Code.:

Synonyms:methyl (1'R,4'S)-2-(4'-benzoyloxy-2'-cyclohexen-1'-yl)-2-N-[6''-bromo-3'',4''-(methylene-dioxy)benzyl]carbamoylacetate

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Chemical Property of methyl (1'R,4'S)-2-(4'-benzoyloxy-2'-cyclohexen-1'-yl)-2-N-[6''-bromo-3'',4''-(methylene-dioxy)benzyl]carbamoylacetate

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Technology Process of methyl (1'R,4'S)-2-(4'-benzoyloxy-2'-cyclohexen-1'-yl)-2-N-[6''-bromo-3'',4''-(methylene-dioxy)benzyl]carbamoylacetate

There total 8 articles about methyl (1'R,4'S)-2-(4'-benzoyloxy-2'-cyclohexen-1'-yl)-2-N-[6''-bromo-3'',4''-(methylene-dioxy)benzyl]carbamoylacetate 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: 83.0%

: 885603-45-2
methyl N-[6-bromo-3,4-(methylenedioxy)-benzyl]carbamoylacetate

: 77300-23-3,881832-47-9
cyclohex-(±)-(1R*,4S*)-2-ene-1,4-diyl dibenzoate

: 888316-54-9
methyl (1'R,4'S)-2-(4'-benzoyloxy-2'-cyclohexen-1'-yl)-2-N-[6''-bromo-3'',4''-(methylene-dioxy)benzyl]carbamoylacetate

Guidance literature:: methyl N-[6-bromo-3,4-(methylenedioxy)-benzyl]carbamoylacetate; With lithium diisopropyl amide; In tetrahydrofuran; at -78 ℃;

cyclohex-(±)-(1R*,4S*)-2-ene-1,4-diyl dibenzoate; With chiral biphenol-based monodentate phosphoramidite ligand; bis(η3-allyl-μ-chloropalladium(II)); In tetrahydrofuran; at -60 ℃; for 8h;
DOI:10.1021/ol060181v

Reference yield: 19.0%

: 885603-45-2
methyl N-[6-bromo-3,4-(methylenedioxy)-benzyl]carbamoylacetate

: 77300-23-3,881832-47-9
cyclohex-(±)-(1R*,4S*)-2-ene-1,4-diyl dibenzoate

: 888316-54-9
methyl (1'R,4'S)-2-(4'-benzoyloxy-2'-cyclohexen-1'-yl)-2-N-[6''-bromo-3'',4''-(methylene-dioxy)benzyl]carbamoylacetate

: 1,4-bis[{2-bromo-4,5-(methylenedioxy)benzyl}carbamoyl(methoxycarbonyl)methyl]cyclohex-2-ene

Guidance literature:: With chiral biphenyl-based reagent; lithium diisopropyl amide; bis(η3-allyl-μ-chloropalladium(II)); In tetrahydrofuran; at -60 ℃; for 8h;
DOI:10.1016/j.tetasy.2005.12.035

Reference yield:

: 120-57-0,30024-74-9
piperonal

: 888316-54-9
methyl (1'R,4'S)-2-(4'-benzoyloxy-2'-cyclohexen-1'-yl)-2-N-[6''-bromo-3'',4''-(methylene-dioxy)benzyl]carbamoylacetate

Guidance literature:: Multi-step reaction with 5 steps

1: 70 percent / Br₂; acetic acid; I₂ / CS₂ / 48 h / 20 °C

2: 93 percent / hydroxylamine hydrochloride; NaHCO₃ / H₂O; ethanol / -20 - 20 °C

3: 91 percent / HCl; zinc / tetrahydrofuran / 2.5 h / Heating

4: 86 percent / triethylamine / CH₂Cl₂ / 0 - 20 °C

5: LDA; chiral biphenyl-based reagent / [Pd(allyl)Cl]2 / tetrahydrofuran / 12 h / -78 - 0 °C

With hydrogenchloride; chiral biphenyl-based reagent; hydroxylamine hydrochloride; bromine; iodine; sodium hydrogencarbonate; acetic acid; triethylamine; zinc; lithium diisopropyl amide; bis(η3-allyl-μ-chloropalladium(II)); In tetrahydrofuran; carbon disulfide; ethanol; dichloromethane; water;
DOI:10.1016/j.tetasy.2005.12.035