(S)-(E)-3-(3,4-Dihydroxy-5-methoxybenzyl)-2-(3,4,5-trimethoxybenzylidene)butanolide

Base Information

Chemical Name:(S)-(E)-3-(3,4-Dihydroxy-5-methoxybenzyl)-2-(3,4,5-trimethoxybenzylidene)butanolide
CAS No.:146236-44-4
Molecular Formula:C₂₂H₂₄O₈
Molecular Weight:416.428
Hs Code.:

Synonyms:(S)-(E)-3-(3,4-Dihydroxy-5-methoxybenzyl)-2-(3,4,5-trimethoxybenzylidene)butanolide

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (S)-(E)-3-(3,4-Dihydroxy-5-methoxybenzyl)-2-(3,4,5-trimethoxybenzylidene)butanolide

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Technology Process of (S)-(E)-3-(3,4-Dihydroxy-5-methoxybenzyl)-2-(3,4,5-trimethoxybenzylidene)butanolide

There total 11 articles about (S)-(E)-3-(3,4-Dihydroxy-5-methoxybenzyl)-2-(3,4,5-trimethoxybenzylidene)butanolide 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: 97.0%

: 146236-45-5
(S)-(E)-3-<5-Methoxy-3,4-(methylenedioxy)benzyl>-2-(3,4,5-trimethoxybenzylidene)butanolide

: 146236-44-4
(S)-(E)-3-(3,4-Dihydroxy-5-methoxybenzyl)-2-(3,4,5-trimethoxybenzylidene)butanolide

Guidance literature:: With boron trichloride; In dichloromethane; at 0 ℃; for 0.5h;
DOI:10.1016/0040-4020(95)00702-A

Reference yield:

: 143616-17-5
(S)-(E)-3-<5-Methoxy-3,4-(methylenedioxy)benzyl>butanolide

: 146236-44-4
(S)-(E)-3-(3,4-Dihydroxy-5-methoxybenzyl)-2-(3,4,5-trimethoxybenzylidene)butanolide

Guidance literature:: Multi-step reaction with 2 steps

1: 1.) diisopropylamine, n-butyllithium; 2.) triethylamine, acetic anhydride, dimethylaminopyridine; 3.) 1,8-diazabicyclo<5.4.0>undec-7-ene / 1.) THF, -70 deg C, 5 min; 2.) CH₂Cl₂, r.t., 1 h; 3.) toluene, 80 deg C, 1.5 h

2: 1.) BCl₃; 2.) 2N HCl / 1.) CH₂Cl₂, 0 deg C, 30 min; 2.) MeOH, r.t., 2 h

With hydrogenchloride; dmap; n-butyllithium; acetic anhydride; boron trichloride; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; diisopropylamine;
DOI:10.3987/com-95-s45

Reference yield:

: 78173-83-8
(E)-3-methoxycarbonyl-4-<5-methoxy-3,4-(methylenedioxy)phenyl>but-3-enoic acid

: 146236-44-4
(S)-(E)-3-(3,4-Dihydroxy-5-methoxybenzyl)-2-(3,4,5-trimethoxybenzylidene)butanolide

Guidance literature:: Multi-step reaction with 4 steps

1: 84 percent / Rh(COD)2BF₄, (R,R)-MOD-DIOP, Et₃N, hydrogen / methanol / 42 h / Ambient temperature

2: 93 percent / KOH, CaCl₂, NaBH₄ / ethanol / 12 h / 0 °C

4: 97 percent / BCl₃ / CH₂Cl₂ / 0.5 h / 0 °C

With potassium hydroxide; sodium tetrahydroborate; rhodium(I)-bis(1,5-cyclooctadiene) tetrafluoroborate; hydrogen; boron trichloride; (4R-trans)-<(2,2-dimethyl-1,3-dioxolane-4,5-diyl)bis(methylene)>bis; triethylamine; calcium chloride; In methanol; ethanol; dichloromethane;
DOI:10.1016/0040-4020(95)00702-A