(+/-)-(1α,2α,4bβ,10α)-Ethyl 2-(benzoyloxy)-8,8-(ethylenedioxy)-1-(methoxycarbonyl)-7-<(methoxymethyl)oxy>-1-methylgibb-4a(10a)-ene-10-carboxylate

Base Information

Chemical Name:(+/-)-(1α,2α,4bβ,10α)-Ethyl 2-(benzoyloxy)-8,8-(ethylenedioxy)-1-(methoxycarbonyl)-7-<(methoxymethyl)oxy>-1-methylgibb-4a(10a)-ene-10-carboxylate
CAS No.:75758-97-3
Molecular Formula:C₃₂H₄₀O₁₀
Molecular Weight:584.664
Hs Code.:

Synonyms:(+/-)-(1α,2α,4bβ,10α)-Ethyl 2-(benzoyloxy)-8,8-(ethylenedioxy)-1-(methoxycarbonyl)-7-<(methoxymethyl)oxy>-1-methylgibb-4a(10a)-ene-10-carboxylate

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Chemical Property of (+/-)-(1α,2α,4bβ,10α)-Ethyl 2-(benzoyloxy)-8,8-(ethylenedioxy)-1-(methoxycarbonyl)-7-<(methoxymethyl)oxy>-1-methylgibb-4a(10a)-ene-10-carboxylate

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Technology Process of (+/-)-(1α,2α,4bβ,10α)-Ethyl 2-(benzoyloxy)-8,8-(ethylenedioxy)-1-(methoxycarbonyl)-7-<(methoxymethyl)oxy>-1-methylgibb-4a(10a)-ene-10-carboxylate

There total 15 articles about (+/-)-(1α,2α,4bβ,10α)-Ethyl 2-(benzoyloxy)-8,8-(ethylenedioxy)-1-(methoxycarbonyl)-7-<(methoxymethyl)oxy>-1-methylgibb-4a(10a)-ene-10-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:

: 75758-96-2
(+/-)-(1α,4bβ,10α)-8,8-(Ethylenedioxy)-2-methoxy-1-(methoxycarbonyl)-7-<(methoxymethyl)oxy>-1-methylgibba-2,4a(10a)-diene-10-carboxylic acid

: 75758-97-3
(+/-)-(1α,2α,4bβ,10α)-Ethyl 2-(benzoyloxy)-8,8-(ethylenedioxy)-1-(methoxycarbonyl)-7-<(methoxymethyl)oxy>-1-methylgibb-4a(10a)-ene-10-carboxylate

Guidance literature:: Multi-step reaction with 3 steps

1: 77 percent / aq. mercury(II) nitrate / acetonitrile / 18 h / 24 °C

2: 90 percent / NaBH₄ / ethanol / 1.5 h / 0 °C

With sodium tetrahydroborate; mercury(II) nitrate; In ethanol; acetonitrile;
DOI:10.1021/ja00541a072

Reference yield:

: 91156-88-6
(+/-)-(1α,4bβ,10α)-8,8-(Ethylenedioxy)-1-(methoxycarbonyl)-7-<(methoxymethyl)oxy>-1-methyl-2-oxogibb-4a(10a)-ene-10-carboxylic acid

: 75758-97-3
(+/-)-(1α,2α,4bβ,10α)-Ethyl 2-(benzoyloxy)-8,8-(ethylenedioxy)-1-(methoxycarbonyl)-7-<(methoxymethyl)oxy>-1-methylgibb-4a(10a)-ene-10-carboxylate

Guidance literature:: Multi-step reaction with 2 steps

1: 90 percent / NaBH₄ / ethanol / 1.5 h / 0 °C

With sodium tetrahydroborate; In ethanol;
DOI:10.1021/ja00541a072

Reference yield:

: 91127-20-7
7-Cyano-7-hydroxy-2-methoxy-6,7,8,9-tetrahydro-5H-fluorene-1-carboxylic acid methyl ester

: 75758-97-3
(+/-)-(1α,2α,4bβ,10α)-Ethyl 2-(benzoyloxy)-8,8-(ethylenedioxy)-1-(methoxycarbonyl)-7-<(methoxymethyl)oxy>-1-methylgibb-4a(10a)-ene-10-carboxylate

Guidance literature:: Multi-step reaction with 14 steps

1: HCl / 16 h / 25 °C

2: aq. KOH / 2 h / 25 °C

3: 90 percent / 1,2-dichloro-ethane / 3 h / Heating

4: oxalyl chloride, DMF / CH₂Cl₂ / 1.) 0 deg C, 2 h, 2.) 25 deg C, 3 h

5: diethyl ether / -20 °C

6: trifluoroacetic acid / CH₂Cl₂ / 0.17 h / -20 °C

7: aq. K₂CO₃ / methanol; tetrahydrofuran / 1.5 h / 24 °C

8: 95 percent / p-toluenesulfonic acid / 1,2-dichloro-ethane / 16 h / Heating

9: 98 percent / i-Pr₂NEt / CH₂Cl₂ / 16 h / 25 °C

10: 1.) lithium N-tert-butyl-N-cyclohexylamide, HMPA / 1.) THF, -20 deg C, 5 min, 2.) -78 -> 25 deg C

12: 77 percent / aq. mercury(II) nitrate / acetonitrile / 18 h / 24 °C

13: 90 percent / NaBH₄ / ethanol / 1.5 h / 0 °C

With hydrogenchloride; N,N,N,N,N,N-hexamethylphosphoric triamide; potassium hydroxide; sodium tetrahydroborate; oxalyl dichloride; lithium N-tert-butyl-N-cyclohexylamide; potassium carbonate; toluene-4-sulfonic acid; mercury(II) nitrate; N-ethyl-N,N-diisopropylamine; N,N-dimethyl-formamide; trifluoroacetic acid; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; 1,2-dichloro-ethane; acetonitrile;
DOI:10.1021/ja00541a072