(+/-)-(4bβ,10α)-Benzyl (8,8-ethylenedioxy)-2-methoxy-1-(methoxycarbonyl)-7-<(methoxymethyl)oxy>gibba-1,3,4a(10a)-triene-10-carboxylate

Base Information

Chemical Name:(+/-)-(4bβ,10α)-Benzyl (8,8-ethylenedioxy)-2-methoxy-1-(methoxycarbonyl)-7-<(methoxymethyl)oxy>gibba-1,3,4a(10a)-triene-10-carboxylate
CAS No.:91127-24-1
Molecular Formula:C₃₀H₃₄O₉
Molecular Weight:538.595
Hs Code.:

Synonyms:(+/-)-(4bβ,10α)-Benzyl (8,8-ethylenedioxy)-2-methoxy-1-(methoxycarbonyl)-7-<(methoxymethyl)oxy>gibba-1,3,4a(10a)-triene-10-carboxylate

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Chemical Property of (+/-)-(4bβ,10α)-Benzyl (8,8-ethylenedioxy)-2-methoxy-1-(methoxycarbonyl)-7-<(methoxymethyl)oxy>gibba-1,3,4a(10a)-triene-10-carboxylate

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Technology Process of (+/-)-(4bβ,10α)-Benzyl (8,8-ethylenedioxy)-2-methoxy-1-(methoxycarbonyl)-7-<(methoxymethyl)oxy>gibba-1,3,4a(10a)-triene-10-carboxylate

There total 17 articles about (+/-)-(4bβ,10α)-Benzyl (8,8-ethylenedioxy)-2-methoxy-1-(methoxycarbonyl)-7-<(methoxymethyl)oxy>gibba-1,3,4a(10a)-triene-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: 86.0%

: 100-39-0
benzyl bromide

: 91127-22-9
(+/-)-(4bβ,10α)-8,8-(Ethylenedioxy)-2-methoxy-1-(methoxycarbonyl)-7-<(methoxymethyl)oxy>gibba-1,3,4a(10a)-triene-10-carboxylic acid

: 91127-24-1
(+/-)-(4bβ,10α)-Benzyl (8,8-ethylenedioxy)-2-methoxy-1-(methoxycarbonyl)-7-<(methoxymethyl)oxy>gibba-1,3,4a(10a)-triene-10-carboxylate

Guidance literature:: With potassium carbonate; In N,N-dimethyl-formamide; for 16h;
DOI:10.1021/jo00192a002

Reference yield:

: 15184-99-3
N,N-dimethyl-3-methoxybenzylamine

: 91127-24-1
(+/-)-(4bβ,10α)-Benzyl (8,8-ethylenedioxy)-2-methoxy-1-(methoxycarbonyl)-7-<(methoxymethyl)oxy>gibba-1,3,4a(10a)-triene-10-carboxylate

Guidance literature:: Multi-step reaction with 17 steps

1: 1) n-BuLi / 1) Et₂O, 20h, room temperature 2) 4h

2: 95 percent / tetrahydrofuran / 18 h / 25 °C

3: NaI / acetone / 1.5 h

4: tetrahydrofuran / 16 h / 1) 0 deg C 2) 16h, room temperature

5: 1) PPA / 1) 30 min, 60 deg C 2) THF, water, HCl, 2h

6: hydrogen chloride gas / Ambient temperature

7: 93 percent / KOH / tetrahydrofuran; methanol; H₂O / 2 h / 25 °C

8: 90 percent / 1,2-dichloro-ethane / 3 h / Heating

9: 8.1 g / oxalyl chloride, DMF / CH₂Cl₂ / 1) 0 deg C 2) room temperature

10: 8.0 g / diethyl ether; CH₂Cl₂ / 1) -20 deg C 2) room temperature

11: 71 percent / CF₃CO₂H / CH₂Cl₂ / 0.42 h / -20 °C

12: 89 percent / K₂CO₃, KHCO₃ / tetrahydrofuran; methanol; H₂O / 1) 1h, reflux 2) 0 deg C 3) 1.5h, 20 deg C

13: 95 percent / p-toluenesulfonic acid / 1,2-dichloro-ethane / 16 h / Heating

14: 98 percent / N-diisopropyl-N-ethylamine / CH₂Cl₂ / 1) 0 deg C 2) 16h, 25 deg C

15: 1) lithium tert-butylcyclohexylamide, HMPA / 1) THF, -20 deg C 2) -78 deg C -> room temperature

16: 91 percent / H₂ / 10percent Pd/C / methanol; ethyl acetate / 16 h / 760 Torr / Ambient temperature

17: 86 percent / K₂CO₃ / dimethylformamide / 16 h

With hydrogenchloride; N,N,N,N,N,N-hexamethylphosphoric triamide; potassium hydroxide; n-butyllithium; oxalyl dichloride; lithium N-tert-butyl-N-cyclohexylamide; hydrogen; potassium carbonate; potassium hydrogencarbonate; N-ethyl-N,N-diisopropylamine; N,N-dimethyl-formamide; trifluoroacetic acid; sodium iodide; palladium on activated charcoal; toluene-4-sulfonic acid; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; ethyl acetate; 1,2-dichloro-ethane; N,N-dimethyl-formamide; acetone;
DOI:10.1021/jo00192a002

Reference yield:

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

: 91127-24-1
(+/-)-(4bβ,10α)-Benzyl (8,8-ethylenedioxy)-2-methoxy-1-(methoxycarbonyl)-7-<(methoxymethyl)oxy>gibba-1,3,4a(10a)-triene-10-carboxylate

Guidance literature:: Multi-step reaction with 12 steps

1: hydrogen chloride gas / Ambient temperature

2: 93 percent / KOH / tetrahydrofuran; methanol; H₂O / 2 h / 25 °C

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

4: 8.1 g / oxalyl chloride, DMF / CH₂Cl₂ / 1) 0 deg C 2) room temperature

5: 8.0 g / diethyl ether; CH₂Cl₂ / 1) -20 deg C 2) room temperature

6: 71 percent / CF₃CO₂H / CH₂Cl₂ / 0.42 h / -20 °C

7: 89 percent / K₂CO₃, KHCO₃ / tetrahydrofuran; methanol; H₂O / 1) 1h, reflux 2) 0 deg C 3) 1.5h, 20 deg C

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

9: 98 percent / N-diisopropyl-N-ethylamine / CH₂Cl₂ / 1) 0 deg C 2) 16h, 25 deg C

10: 1) lithium tert-butylcyclohexylamide, HMPA / 1) THF, -20 deg C 2) -78 deg C -> room temperature

11: 91 percent / H₂ / 10percent Pd/C / methanol; ethyl acetate / 16 h / 760 Torr / Ambient temperature

12: 86 percent / K₂CO₃ / dimethylformamide / 16 h

With hydrogenchloride; N,N,N,N,N,N-hexamethylphosphoric triamide; potassium hydroxide; oxalyl dichloride; lithium N-tert-butyl-N-cyclohexylamide; hydrogen; potassium carbonate; potassium hydrogencarbonate; N-ethyl-N,N-diisopropylamine; N,N-dimethyl-formamide; trifluoroacetic acid; palladium on activated charcoal; toluene-4-sulfonic acid; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; ethyl acetate; 1,2-dichloro-ethane; N,N-dimethyl-formamide;
DOI:10.1021/jo00192a002