2-((1S,6R)-5,5-Dimethoxy-4-oxo-bicyclo[4.1.0]hept-2-en-2-yl)-4-(3,4,5-trimethoxy-phenyl)-butyric acid tert-butyl ester

Base Information

Chemical Name:2-((1S,6R)-5,5-Dimethoxy-4-oxo-bicyclo[4.1.0]hept-2-en-2-yl)-4-(3,4,5-trimethoxy-phenyl)-butyric acid tert-butyl ester
CAS No.:79118-06-2
Molecular Formula:C₂₆H₃₆O₈
Molecular Weight:476.567
Hs Code.:

Synonyms:2-((1S,6R)-5,5-Dimethoxy-4-oxo-bicyclo[4.1.0]hept-2-en-2-yl)-4-(3,4,5-trimethoxy-phenyl)-butyric acid tert-butyl ester

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Chemical Property of 2-((1S,6R)-5,5-Dimethoxy-4-oxo-bicyclo[4.1.0]hept-2-en-2-yl)-4-(3,4,5-trimethoxy-phenyl)-butyric acid tert-butyl ester

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Technology Process of 2-((1S,6R)-5,5-Dimethoxy-4-oxo-bicyclo[4.1.0]hept-2-en-2-yl)-4-(3,4,5-trimethoxy-phenyl)-butyric acid tert-butyl ester

There total 7 articles about 2-((1S,6R)-5,5-Dimethoxy-4-oxo-bicyclo[4.1.0]hept-2-en-2-yl)-4-(3,4,5-trimethoxy-phenyl)-butyric acid tert-butyl 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: 7.0%

: 79118-07-3
2-(2-Hydroxy-4,5,5-trimethoxy-bicyclo[4.1.0]hept-3-en-2-yl)-4-(3,4,5-trimethoxy-phenyl)-butyric acid tert-butyl ester

: 79118-06-2
2-((1S,6R)-5,5-Dimethoxy-4-oxo-bicyclo[4.1.0]hept-2-en-2-yl)-4-(3,4,5-trimethoxy-phenyl)-butyric acid tert-butyl ester

: 79118-08-4,79171-77-0
tert-butyl α-(2-hydroxy-4-methoxy-5-oxobicyclo<4.1.0>hept-3-en-1-yl)-α-(β-(3,4,5-trimethoxyphenyl)ethyl)acetate

: 79118-08-4,79171-77-0
tert-butyl α-(2-hydroxy-4-methoxy-5-oxobicyclo<4.1.0>hept-3-en-1-yl)-α-(β-(3,4,5-trimethoxyphenyl)ethyl)acetate

Guidance literature:: With oxalic acid; In tetrahydrofuran; water; for 4h; Yields of byproduct given; Ambient temperature;
DOI:10.1021/ja00409a032

Reference yield:

: 90-50-6
3,4,5-trimethoxycinnamic acid

: 79118-06-2
2-((1S,6R)-5,5-Dimethoxy-4-oxo-bicyclo[4.1.0]hept-2-en-2-yl)-4-(3,4,5-trimethoxy-phenyl)-butyric acid tert-butyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: oxalyl chloride / benzene / 3 h / Ambient temperature

2: 70 percent / N,N-dimethylaniline / diethyl ether / 14 h / Heating

3: 68 percent / 1.) sodium hydride / dimethylsulfoxide / 2.) 55 deg C, 2 h

4: 72 percent / hydrogen / 5percent Pd-C / methanol / 48 h / 2585.7 Torr

5: 1.) lithium diisopropylamide / tetrahydrofuran / 1.) -65 deg C, 65 min, 2.) -60 deg C, 15 min; -60 - 10 deg C, 30 min

6: 7 percent / oxalic acid / tetrahydrofuran; H₂O / 4 h / Ambient temperature

With oxalyl dichloride; hydrogen; oxalic acid; sodium hydride; N,N-dimethyl-aniline; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; water; dimethyl sulfoxide; benzene;
DOI:10.1021/ja00409a032

Reference yield:

: 79118-11-9
tert-butyl 3,4,5-trimethoxycinnamate

: 79118-06-2
2-((1S,6R)-5,5-Dimethoxy-4-oxo-bicyclo[4.1.0]hept-2-en-2-yl)-4-(3,4,5-trimethoxy-phenyl)-butyric acid tert-butyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: 68 percent / 1.) sodium hydride / dimethylsulfoxide / 2.) 55 deg C, 2 h

2: 72 percent / hydrogen / 5percent Pd-C / methanol / 48 h / 2585.7 Torr

3: 1.) lithium diisopropylamide / tetrahydrofuran / 1.) -65 deg C, 65 min, 2.) -60 deg C, 15 min; -60 - 10 deg C, 30 min

4: 7 percent / oxalic acid / tetrahydrofuran; H₂O / 4 h / Ambient temperature

With hydrogen; oxalic acid; sodium hydride; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; methanol; water; dimethyl sulfoxide;
DOI:10.1021/ja00409a032