2-((1R,5S,6S)-6-Benzoyloxy-5-bromo-3-methoxycarbonyl-cyclohex-2-enyloxy)-2-dimethylaminomethyl-malonic acid dimethyl ester

Base Information

Chemical Name:2-((1R,5S,6S)-6-Benzoyloxy-5-bromo-3-methoxycarbonyl-cyclohex-2-enyloxy)-2-dimethylaminomethyl-malonic acid dimethyl ester
CAS No.:80631-83-0
Molecular Formula:C₂₃H₂₈BrNO₉
Molecular Weight:542.381
Hs Code.:

Synonyms:2-((1R,5S,6S)-6-Benzoyloxy-5-bromo-3-methoxycarbonyl-cyclohex-2-enyloxy)-2-dimethylaminomethyl-malonic acid dimethyl ester

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Chemical Property of 2-((1R,5S,6S)-6-Benzoyloxy-5-bromo-3-methoxycarbonyl-cyclohex-2-enyloxy)-2-dimethylaminomethyl-malonic acid dimethyl ester

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Technology Process of 2-((1R,5S,6S)-6-Benzoyloxy-5-bromo-3-methoxycarbonyl-cyclohex-2-enyloxy)-2-dimethylaminomethyl-malonic acid dimethyl ester

There total 11 articles about 2-((1R,5S,6S)-6-Benzoyloxy-5-bromo-3-methoxycarbonyl-cyclohex-2-enyloxy)-2-dimethylaminomethyl-malonic acid dimethyl 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: 100.0%

: 33797-51-2
eschenmoser's salt

: 80631-82-9
methyl (3β,4α,5β)-3--4-(benzoyloxy)-5-bromo-1-cyclohexene-1-carboxylate

: 80631-83-0
2-((1R,5S,6S)-6-Benzoyloxy-5-bromo-3-methoxycarbonyl-cyclohex-2-enyloxy)-2-dimethylaminomethyl-malonic acid dimethyl ester

Guidance literature:: With triethylamine; In dichloromethane; for 3h;
DOI:10.1021/ja00389a025

Reference yield:

: 3298-40-6
mesoxalate de methyle

: 80631-83-0
2-((1R,5S,6S)-6-Benzoyloxy-5-bromo-3-methoxycarbonyl-cyclohex-2-enyloxy)-2-dimethylaminomethyl-malonic acid dimethyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: 83 percent / toluene / 1.) 40 deg C, 12 h, 2.) 80 deg C 3 h

2: 50 percent / SOCl₂, pyridine / tetrahydrofuran / 1.) -20 deg C , 0.5 h, 2.) 0 deg C, 1 h

3: 66 percent / N-bromosuccinimide / benzene / Ambient temperature

4: Et₃N / CH₂Cl₂ / 72 h

With pyridine; N-Bromosuccinimide; thionyl chloride; triethylamine; In tetrahydrofuran; dichloromethane; toluene; benzene;
DOI:10.1021/ja00389a025

Reference yield:

: 4372-89-8,4372-91-2,14671-74-0,16613-43-7,16613-44-8,40983-58-2,121468-33-5,141781-68-2
methyl 4-epi-shikimate

: 80631-83-0
2-((1R,5S,6S)-6-Benzoyloxy-5-bromo-3-methoxycarbonyl-cyclohex-2-enyloxy)-2-dimethylaminomethyl-malonic acid dimethyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: 72 percent / p-toluenesulfonic acid / toluene / Heating

2: 83 percent / toluene / 1.) 40 deg C, 12 h, 2.) 80 deg C 3 h

3: 50 percent / SOCl₂, pyridine / tetrahydrofuran / 1.) -20 deg C , 0.5 h, 2.) 0 deg C, 1 h

4: 66 percent / N-bromosuccinimide / benzene / Ambient temperature

5: Et₃N / CH₂Cl₂ / 72 h

With pyridine; N-Bromosuccinimide; thionyl chloride; toluene-4-sulfonic acid; triethylamine; In tetrahydrofuran; dichloromethane; toluene; benzene;
DOI:10.1021/ja00389a025