methyl (3β,4α,5β)-3--4-(benzoyloxy)-5-bromo-1-cyclohexene-1-carboxylate

Base Information

• Chemical Name: methyl (3β,4α,5β)-3--4-(benzoyloxy)-5-bromo-1-cyclohexene-1-carboxylate
• CAS No.: 83604-12-0
• Molecular Formula: C₂₀H₂₀BrClO₉
• Molecular Weight: 519.73
• Mol file: 83604-12-0.mol

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

Chemical Property of methyl (3β,4α,5β)-3--4-(benzoyloxy)-5-bromo-1-cyclohexene-1-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl (3β,4α,5β)-3--4-(benzoyloxy)-5-bromo-1-cyclohexene-1-carboxylate

There total 7 articles about methyl (3β,4α,5β)-3--4-(benzoyloxy)-5-bromo-1-cyclohexene-1-carboxylate 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: 7.0%

methyl (1α,5α,6α)-5--8-phenyl-7,9-dioxabicyclo<4.3.0>non-3-ene-3-carboxylate (80631-80-7,83889-53-6,83889-54-7) → 2-((1R,5R,6S)-5-Benzoyloxy-6-bromo-3-methoxycarbonyl-cyclohex-2-enyloxy)-2-chloro-malonic acid dimethyl ester + methyl (3β,4α,5β)-3--4-(benzoyloxy)-5-bromo-1-cyclohexene-1-carboxylate (83604-12-0)

Guidance literature:

With N-Bromosuccinimide; In benzene; Ambient temperature;

DOI:10.1021/ja00389a025

Reference yield:

mesoxalate de methyle (3298-40-6) → methyl (3β,4α,5β)-3--4-(benzoyloxy)-5-bromo-1-cyclohexene-1-carboxylate (83604-12-0)

Guidance literature:

Multi-step reaction with 3 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

With pyridine; N-Bromosuccinimide; thionyl chloride; In tetrahydrofuran; toluene; benzene;

DOI:10.1021/ja00389a025

Reference yield:

methyl 4-epi-shikimate (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 (3β,4α,5β)-3--4-(benzoyloxy)-5-bromo-1-cyclohexene-1-carboxylate (83604-12-0)

Guidance literature:

Multi-step reaction with 4 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

With pyridine; N-Bromosuccinimide; thionyl chloride; toluene-4-sulfonic acid; In tetrahydrofuran; toluene; benzene;

DOI:10.1021/ja00389a025

upstream raw materials:

methyl (1α,5α,6α)-5--8-phenyl-7,9-dioxabicyclo<4.3.0>non-3-ene-3-carboxylate

mesoxalate de methyle

methyl 4-epi-shikimate

benzaldehyde

Downstream raw materials:

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

methyl (3β,4α,5β)-3-<<1-(methoxycarbonyl)ethenyl>oxy>-4-(benzoyloxy)-5-bromo-1-cyclohexene-1-carboxylate

(3S,4R,5R)-4-Hydroxy-3-(1-methoxycarbonyl-vinyloxy)-5-phenylselanyl-cyclohex-1-enecarboxylic acid methyl ester

dimethyl chlorismate