methyl <1(R)-(1α,4α,5β)>-4-(benzoyloxy)-1-hydroxy-5-<<1-(methoxycarbonyl)ethenyl>oxy>-2-cyclohexane-1-carboxylate

Base Information

Chemical Name:methyl <1(R)-(1α,4α,5β)>-4-(benzoyloxy)-1-hydroxy-5-<<1-(methoxycarbonyl)ethenyl>oxy>-2-cyclohexane-1-carboxylate
CAS No.:105539-82-0
Molecular Formula:C₁₉H₂₀O₈
Molecular Weight:376.363
Hs Code.:

Synonyms:methyl <1(R)-(1α,4α,5β)>-4-(benzoyloxy)-1-hydroxy-5-<<1-(methoxycarbonyl)ethenyl>oxy>-2-cyclohexane-1-carboxylate

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Chemical Property of methyl <1(R)-(1α,4α,5β)>-4-(benzoyloxy)-1-hydroxy-5-<<1-(methoxycarbonyl)ethenyl>oxy>-2-cyclohexane-1-carboxylate

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Technology Process of methyl <1(R)-(1α,4α,5β)>-4-(benzoyloxy)-1-hydroxy-5-<<1-(methoxycarbonyl)ethenyl>oxy>-2-cyclohexane-1-carboxylate

There total 6 articles about methyl <1(R)-(1α,4α,5β)>-4-(benzoyloxy)-1-hydroxy-5-<<1-(methoxycarbonyl)ethenyl>oxy>-2-cyclohexane-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: 74.0%

: 105539-81-9
methyl<1(R)-(1α,4α,5β)>-4-(benzoyloxy)-1-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-5-<<1-(methoxycarbonyl)ethenyl>oxy>-2-cyclohexene-1-carboxylate

: 105539-82-0
methyl <1(R)-(1α,4α,5β)>-4-(benzoyloxy)-1-hydroxy-5-<<1-(methoxycarbonyl)ethenyl>oxy>-2-cyclohexane-1-carboxylate

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 0 ℃; for 1h;
DOI:10.1021/ja00285a031

Reference yield:

: 216662-57-6
(1S,3R,4R,5R)-3,4-O-Benzylidene-1,3,4-trihydroxy-6-oxabicyclo<3.2.1>octan-7-one

: 105539-82-0
methyl <1(R)-(1α,4α,5β)>-4-(benzoyloxy)-1-hydroxy-5-<<1-(methoxycarbonyl)ethenyl>oxy>-2-cyclohexane-1-carboxylate

Guidance literature:: Multi-step reaction with 6 steps

1: 86 percent / N-bromosuccinimide, AIBN / benzene / 1 h / Heating

2: 79 percent / diazabicycloundecane / acetonitrile / 16 h / Heating

3: 90 percent / p-toluenesulfonic acid / methanol / 6 h / 53 °C

4: 75 percent / rhodium acethate / benzene / 2.5 h / Heating

5: 1.)triethylamine, N,N-dimethylmethyleneammonium iodide 2.) iodomethane / 1.) CH₂Cl₂, 21 deg C, 21h; 2.) reflux, 6h

6: 74 percent / tetrabuthylammonium fluoride / tetrahydrofuran / 1 h / 0 °C

With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); diazabicycloundecane; rhodium acethate; tetrabutyl ammonium fluoride; eschenmoser's salt; triethylamine; methyl iodide; toluene-4-sulfonic acid; In tetrahydrofuran; methanol; acetonitrile; benzene;
DOI:10.1021/ja00285a031

Reference yield:

: 105539-78-4
(1R,3S,4S,5R)-3-bromo-1-hydroxy-7-oxo-6-oxabicyclo[3.2.1]oct-4-yl benzoate

: 105539-82-0
methyl <1(R)-(1α,4α,5β)>-4-(benzoyloxy)-1-hydroxy-5-<<1-(methoxycarbonyl)ethenyl>oxy>-2-cyclohexane-1-carboxylate

Guidance literature:: Multi-step reaction with 5 steps

1: 79 percent / diazabicycloundecane / acetonitrile / 16 h / Heating

2: 90 percent / p-toluenesulfonic acid / methanol / 6 h / 53 °C

3: 75 percent / rhodium acethate / benzene / 2.5 h / Heating

4: 1.)triethylamine, N,N-dimethylmethyleneammonium iodide 2.) iodomethane / 1.) CH₂Cl₂, 21 deg C, 21h; 2.) reflux, 6h

5: 74 percent / tetrabuthylammonium fluoride / tetrahydrofuran / 1 h / 0 °C

With diazabicycloundecane; rhodium acethate; tetrabutyl ammonium fluoride; eschenmoser's salt; triethylamine; methyl iodide; toluene-4-sulfonic acid; In tetrahydrofuran; methanol; acetonitrile; benzene;
DOI:10.1021/ja00285a031