(E)-3-[4-Benzyloxy-3-((1R,2R)-2-tert-butoxycarbonylamino-1-ethyl-3-methoxymethoxy-1-methyl-propoxy)-phenyl]-acrylic acid ethyl ester

Base Information

• Chemical Name: (E)-3-[4-Benzyloxy-3-((1R,2R)-2-tert-butoxycarbonylamino-1-ethyl-3-methoxymethoxy-1-methyl-propoxy)-phenyl]-acrylic acid ethyl ester
• CAS No.: 401606-62-0
• Molecular Formula: C₃₁H₄₃NO₈
• Molecular Weight: 557.684

Synonyms:(E)-3-[4-Benzyloxy-3-((1R,2R)-2-tert-butoxycarbonylamino-1-ethyl-3-methoxymethoxy-1-methyl-propoxy)-phenyl]-acrylic acid ethyl ester

Chemical Property of (E)-3-[4-Benzyloxy-3-((1R,2R)-2-tert-butoxycarbonylamino-1-ethyl-3-methoxymethoxy-1-methyl-propoxy)-phenyl]-acrylic acid ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

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Technology Process of (E)-3-[4-Benzyloxy-3-((1R,2R)-2-tert-butoxycarbonylamino-1-ethyl-3-methoxymethoxy-1-methyl-propoxy)-phenyl]-acrylic acid ethyl ester

There total 10 articles about (E)-3-[4-Benzyloxy-3-((1R,2R)-2-tert-butoxycarbonylamino-1-ethyl-3-methoxymethoxy-1-methyl-propoxy)-phenyl]-acrylic acid ethyl 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: 96.0%

ethyl acrylate (140-88-5,9003-32-1) + [(1R,2R)-2-(2-Benzyloxy-5-bromo-phenoxy)-1-methoxymethoxymethyl-2-methyl-butyl]-carbamic acid tert-butyl ester (401606-61-9) → (E)-3-[4-Benzyloxy-3-((1R,2R)-2-tert-butoxycarbonylamino-1-ethyl-3-methoxymethoxy-1-methyl-propoxy)-phenyl]-acrylic acid ethyl ester (401606-62-0)

Guidance literature:

With triethylamine; tris-(o-tolyl)phosphine; palladium diacetate; In acetonitrile; for 6h; Heating;

DOI:10.1021/ja710363p

Reference yield:

(2R,3R) 2-<(tert-butoxycarbonyl)amino>-3-methyl-1,3-pentanediol (167102-72-9) → (E)-3-[4-Benzyloxy-3-((1R,2R)-2-tert-butoxycarbonylamino-1-ethyl-3-methoxymethoxy-1-methyl-propoxy)-phenyl]-acrylic acid ethyl ester (401606-62-0)

Guidance literature:

Multi-step reaction with 9 steps

1: 3.09 g / iPr₂NEt / CH₂Cl₂ / 14 h / 25 °C

2: 78 percent / TFA / CH₂Cl₂ / 0.83 h / 0 °C

3: 78.2 percent / KHMDS / tetrahydrofuran; toluene / 2 h / 0 °C

4: 81 percent / Et₃N / CH₂Cl₂ / 0 - 20 °C

5: 56 percent / NaH₂PO₂; pyridine; AcOH / Raney nickel / H₂O / 4.33 h / 0 - 47 °C

6: 2.49 g / aq. H₂O₂; bis(2-nitrophenyl)diselenide / CH₂Cl₂ / 24 h / 20 °C

7: 73 percent / methanilic KOH / 1.5 h / 20 °C

8: 96 percent / K₂CO₃; n-Bu₄NI / dimethylformamide / 18 h

9: 95 percent / Et₃N; (o-tolyl)3P; Pd(OAc)2 / acetonitrile / 6 h / Heating

With pyridine; palladium diacetate; potassium hydroxide; sodium hypophosphite; bis(o-nitrophenyl) diselenide; dihydrogen peroxide; tetra-(n-butyl)ammonium iodide; potassium hexamethylsilazane; potassium carbonate; acetic acid; triethylamine; N-ethyl-N,N-diisopropylamine; tris-(o-tolyl)phosphine; trifluoroacetic acid; nickel; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; toluene; acetonitrile; 6: Dakin oxidation / 9: Heck reaction;

DOI:10.1021/ja017277z

Reference yield:

(R)-4-((R)-1-hydroxy-1-methylpropyl)-2,2-dimethyl oxazolidine-3-carboxylic acid tert-butyl ester (167102-68-3) → (E)-3-[4-Benzyloxy-3-((1R,2R)-2-tert-butoxycarbonylamino-1-ethyl-3-methoxymethoxy-1-methyl-propoxy)-phenyl]-acrylic acid ethyl ester (401606-62-0)

Guidance literature:

Multi-step reaction with 10 steps

1: p-TsOH / methanol / 0.5 h / 20 °C

2: 3.09 g / iPr₂NEt / CH₂Cl₂ / 14 h / 25 °C

3: 78 percent / TFA / CH₂Cl₂ / 0.83 h / 0 °C

4: 78.2 percent / KHMDS / tetrahydrofuran; toluene / 2 h / 0 °C

5: 81 percent / Et₃N / CH₂Cl₂ / 0 - 20 °C

6: 56 percent / NaH₂PO₂; pyridine; AcOH / Raney nickel / H₂O / 4.33 h / 0 - 47 °C

7: 2.49 g / aq. H₂O₂; bis(2-nitrophenyl)diselenide / CH₂Cl₂ / 24 h / 20 °C

8: 73 percent / methanilic KOH / 1.5 h / 20 °C

9: 96 percent / K₂CO₃; n-Bu₄NI / dimethylformamide / 18 h

10: 95 percent / Et₃N; (o-tolyl)3P; Pd(OAc)2 / acetonitrile / 6 h / Heating

With pyridine; palladium diacetate; potassium hydroxide; sodium hypophosphite; bis(o-nitrophenyl) diselenide; dihydrogen peroxide; tetra-(n-butyl)ammonium iodide; potassium hexamethylsilazane; potassium carbonate; toluene-4-sulfonic acid; acetic acid; triethylamine; N-ethyl-N,N-diisopropylamine; tris-(o-tolyl)phosphine; trifluoroacetic acid; nickel; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; toluene; acetonitrile; 7: Dakin oxidation / 10: Heck reaction;

DOI:10.1021/ja017277z

upstream raw materials:

ethyl acrylate

[(1R,2R)-2-(2-Benzyloxy-5-bromo-phenoxy)-1-methoxymethoxymethyl-2-methyl-butyl]-carbamic acid tert-butyl ester

(2R,3R) 2-<(tert-butoxycarbonyl)amino>-3-methyl-1,3-pentanediol

(R)-4-((R)-1-hydroxy-1-methylpropyl)-2,2-dimethyl oxazolidine-3-carboxylic acid tert-butyl ester

Downstream raw materials:

(2S,3R)-3-[4-Benzyloxy-3-((1R,2R)-2-tert-butoxycarbonylamino-1-ethyl-3-methoxymethoxy-1-methyl-propoxy)-phenyl]-2-benzyloxycarbonylamino-3-hydroxy-propionic acid ethyl ester

C₃₉H₅₂N₂O₁₁

C₃₉H₅₂N₂O₁₁

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