(2R,3R)-(-)-5-{(1S)-1-[(1R)-N-Benzyl-1-phenylethylamino]-2-(tert-butoxycarbonyl)ethyl}-2-(3,4-dimethoxyphenyl)-2,3-dihydrobenzofuran-3-carboxylic acid

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Chemical Name:(2R,3R)-(-)-5-{(1S)-1-[(1R)-N-Benzyl-1-phenylethylamino]-2-(tert-butoxycarbonyl)ethyl}-2-(3,4-dimethoxyphenyl)-2,3-dihydrobenzofuran-3-carboxylic acid
CAS No.:254975-92-3
Molecular Formula:C₃₉H₄₃NO₇
Molecular Weight:637.773
Hs Code.:

Synonyms:(2R,3R)-(-)-5-{(1S)-1-[(1R)-N-Benzyl-1-phenylethylamino]-2-(tert-butoxycarbonyl)ethyl}-2-(3,4-dimethoxyphenyl)-2,3-dihydrobenzofuran-3-carboxylic acid

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Chemical Property of (2R,3R)-(-)-5-{(1S)-1-[(1R)-N-Benzyl-1-phenylethylamino]-2-(tert-butoxycarbonyl)ethyl}-2-(3,4-dimethoxyphenyl)-2,3-dihydrobenzofuran-3-carboxylic acid

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Technology Process of (2R,3R)-(-)-5-{(1S)-1-[(1R)-N-Benzyl-1-phenylethylamino]-2-(tert-butoxycarbonyl)ethyl}-2-(3,4-dimethoxyphenyl)-2,3-dihydrobenzofuran-3-carboxylic acid

There total 14 articles about (2R,3R)-(-)-5-{(1S)-1-[(1R)-N-Benzyl-1-phenylethylamino]-2-(tert-butoxycarbonyl)ethyl}-2-(3,4-dimethoxyphenyl)-2,3-dihydrobenzofuran-3-carboxylic acid 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: 48.0%

: 38235-77-7
(R)-N-benzyl-1-phenylethylamine

: (2S,3S)-5-((E)-2-tert-Butoxycarbonyl-vinyl)-2-(3,4-dimethoxy-phenyl)-2,3-dihydro-benzofuran-3-carboxylic acid

: 254975-92-3
(2R,3R)-(-)-5-{(1S)-1-[(1R)-N-Benzyl-1-phenylethylamino]-2-(tert-butoxycarbonyl)ethyl}-2-(3,4-dimethoxyphenyl)-2,3-dihydrobenzofuran-3-carboxylic acid

Guidance literature:: With n-butyllithium; In tetrahydrofuran; at -78 ℃; for 2h;
DOI:10.1016/S0040-4039(99)01835-3

Reference yield: 48.0%

: 38235-77-7
(R)-N-benzyl-1-phenylethylamine

: 254975-91-2
(2R,3R)-(-)-5-[2-(tert-Butoxycarbonyl)vinyl]-2-(3,4-dimethoxyphenyl)-2,3-dihydrobenzofuran-3-carboxylic acid

: 254975-92-3
(2R,3R)-(-)-5-{(1S)-1-[(1R)-N-Benzyl-1-phenylethylamino]-2-(tert-butoxycarbonyl)ethyl}-2-(3,4-dimethoxyphenyl)-2,3-dihydrobenzofuran-3-carboxylic acid

Guidance literature:: (R)-N-benzyl-1-phenylethylamine; With n-butyllithium; In tetrahydrofuran; hexane; at 0 ℃; for 0.333333h;

(2R,3R)-(-)-5-[2-(tert-Butoxycarbonyl)vinyl]-2-(3,4-dimethoxyphenyl)-2,3-dihydrobenzofuran-3-carboxylic acid; In tetrahydrofuran; hexane; at -78 ℃; for 2h;
DOI:10.1039/a909816j

Reference yield:

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

: 254975-92-3
(2R,3R)-(-)-5-{(1S)-1-[(1R)-N-Benzyl-1-phenylethylamino]-2-(tert-butoxycarbonyl)ethyl}-2-(3,4-dimethoxyphenyl)-2,3-dihydrobenzofuran-3-carboxylic acid

Guidance literature:: Multi-step reaction with 6 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

5.1: 89 percent / Ba(OH)2*8H₂O / tetrahydrofuran; methanol / 1 h / 20 °C

6.1: BuLi / tetrahydrofuran; hexane / 0.33 h / 0 °C

6.2: 48 percent / tetrahydrofuran; hexane / 2 h / -78 °C

With barium dihydroxide; 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; methanol; hexane; dichloromethane; 1.1: enolization / 1.2: Addition / 2.1: Cyclization / 3.1: Methylation / 4.1: Arylation / 5.1: Hydrolysis / 6.1: Metallation / 6.2: Addition;
DOI:10.1039/a909816j