(-)-Methyl (2R,3R)-5-[2-(tert-butoxycarbonyl)vinyl]-2-(3,4-dimethoxyphenyl)-2,3-dihydrobenzofuran-3-carboxylate

Base Information

Chemical Name:(-)-Methyl (2R,3R)-5-[2-(tert-butoxycarbonyl)vinyl]-2-(3,4-dimethoxyphenyl)-2,3-dihydrobenzofuran-3-carboxylate
CAS No.:254975-90-1
Molecular Formula:C₂₅H₂₈O₇
Molecular Weight:440.493
Hs Code.:

Synonyms:(-)-Methyl (2R,3R)-5-[2-(tert-butoxycarbonyl)vinyl]-2-(3,4-dimethoxyphenyl)-2,3-dihydrobenzofuran-3-carboxylate

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Chemical Property of (-)-Methyl (2R,3R)-5-[2-(tert-butoxycarbonyl)vinyl]-2-(3,4-dimethoxyphenyl)-2,3-dihydrobenzofuran-3-carboxylate

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Technology Process of (-)-Methyl (2R,3R)-5-[2-(tert-butoxycarbonyl)vinyl]-2-(3,4-dimethoxyphenyl)-2,3-dihydrobenzofuran-3-carboxylate

There total 7 articles about (-)-Methyl (2R,3R)-5-[2-(tert-butoxycarbonyl)vinyl]-2-(3,4-dimethoxyphenyl)-2,3-dihydrobenzofuran-3-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: 85.0%

: 1663-39-4,25232-27-3
tert-Butyl acrylate

: 254975-89-8
(-)-Methyl (2R,3R)-5-bromo-2-(3,4-dimethoxyphenyl)-2,3-dihydrobenzofuran-3-carboxylate

: 254975-90-1
(-)-Methyl (2R,3R)-5-[2-(tert-butoxycarbonyl)vinyl]-2-(3,4-dimethoxyphenyl)-2,3-dihydrobenzofuran-3-carboxylate

Guidance literature:: With triethylamine; palladium diacetate; tris-(o-tolyl)phosphine; at 100 ℃; for 16h;
DOI:10.1039/a909816j

Reference yield:

: 120-14-9
3,4-dimethoxy-benzaldehyde

: 254975-90-1
(-)-Methyl (2R,3R)-5-[2-(tert-butoxycarbonyl)vinyl]-2-(3,4-dimethoxyphenyl)-2,3-dihydrobenzofuran-3-carboxylate

Guidance literature:: Multi-step reaction with 4 steps

1.1: 9-BBN triflate; iPr₂NEt / CH₂Cl₂ / 1 h / 1 °C

1.2: 87 percent / CH₂Cl₂ / 3 h / -75 - 20 °C

2.1: 71 percent / Me₃SiI / CH₂Cl₂ / 1.28 h / 20 °C

3.1: 78 percent / NaOMe / 2 h / 0 °C

4.1: 85 percent / Et₃N / Pd(OAc)2; P(o-tolyl)3 / 16 h / 100 °C

With trimethylsilyl iodide; sodium methylate; triethylamine; N-ethyl-N,N-diisopropylamine; B-(trifluoromethanesulfonyloxy)-9-borabicyclo[3.3.1]nonane; palladium diacetate; tris-(o-tolyl)phosphine; In dichloromethane; 1.1: enolization / 1.2: Addition / 2.1: Cyclization / 3.1: Methylation / 4.1: Arylation;
DOI:10.1039/a909816j

Reference yield:

: 149428-97-7
2-(Benzyloxy)-5-bromophenylacetic acid

: 254975-90-1
(-)-Methyl (2R,3R)-5-[2-(tert-butoxycarbonyl)vinyl]-2-(3,4-dimethoxyphenyl)-2,3-dihydrobenzofuran-3-carboxylate

Guidance literature:: Multi-step reaction with 6 steps

1.1: Et₃N / diethyl ether / 1 h / 0 °C

2.1: BuLi / tetrahydrofuran; hexane; diethyl ether / 0.75 h / -78 - 0 °C

3.1: 9-BBN triflate; iPr₂NEt / CH₂Cl₂ / 1 h / 1 °C

3.2: 87 percent / CH₂Cl₂ / 3 h / -75 - 20 °C

4.1: 71 percent / Me₃SiI / CH₂Cl₂ / 1.28 h / 20 °C

5.1: 78 percent / NaOMe / 2 h / 0 °C

6.1: 85 percent / Et₃N / Pd(OAc)2; P(o-tolyl)3 / 16 h / 100 °C

With n-butyllithium; trimethylsilyl iodide; sodium methylate; triethylamine; N-ethyl-N,N-diisopropylamine; B-(trifluoromethanesulfonyloxy)-9-borabicyclo[3.3.1]nonane; palladium diacetate; tris-(o-tolyl)phosphine; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; 1.1: Acylation / 2.1: Acylation / 3.1: enolization / 3.2: Addition / 4.1: Cyclization / 5.1: Methylation / 6.1: Arylation;
DOI:10.1039/a909816j