{2-benzyloxy-1-[3-(3-{1-[2-tert-butoxycarbonylamino-3-(4-fluoro-3-nitro-phenyl)-propionylamino]-2-hydroxy-ethyl}-5-methoxy-phenoxy)-4-methoxy-phenyl]-ethyl}-carbamic acid tert-butyl ester

Base Information

• Chemical Name: {2-benzyloxy-1-[3-(3-{1-[2-tert-butoxycarbonylamino-3-(4-fluoro-3-nitro-phenyl)-propionylamino]-2-hydroxy-ethyl}-5-methoxy-phenoxy)-4-methoxy-phenyl]-ethyl}-carbamic acid tert-butyl ester
• CAS No.: 331731-34-1
• Molecular Formula: C₄₄H₅₃FN₄O₁₂
• Molecular Weight: 848.923
• Mol file: 331731-34-1.mol

Synonyms:{2-benzyloxy-1-[3-(3-{1-[2-tert-butoxycarbonylamino-3-(4-fluoro-3-nitro-phenyl)-propionylamino]-2-hydroxy-ethyl}-5-methoxy-phenoxy)-4-methoxy-phenyl]-ethyl}-carbamic acid tert-butyl ester

Chemical Property of {2-benzyloxy-1-[3-(3-{1-[2-tert-butoxycarbonylamino-3-(4-fluoro-3-nitro-phenyl)-propionylamino]-2-hydroxy-ethyl}-5-methoxy-phenoxy)-4-methoxy-phenyl]-ethyl}-carbamic acid tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of {2-benzyloxy-1-[3-(3-{1-[2-tert-butoxycarbonylamino-3-(4-fluoro-3-nitro-phenyl)-propionylamino]-2-hydroxy-ethyl}-5-methoxy-phenoxy)-4-methoxy-phenyl]-ethyl}-carbamic acid tert-butyl ester

There total 22 articles about {2-benzyloxy-1-[3-(3-{1-[2-tert-butoxycarbonylamino-3-(4-fluoro-3-nitro-phenyl)-propionylamino]-2-hydroxy-ethyl}-5-methoxy-phenoxy)-4-methoxy-phenyl]-ethyl}-carbamic 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: 72.0%

(R)-N-(tert-butoxycarbonyl)-4-fluoro-3-nitrophenylalanine (173775-54-7) + ((R)-1-{3-[3-((S)-1-Amino-2-hydroxy-ethyl)-5-methoxy-phenoxy]-4-methoxy-phenyl}-2-benzyloxy-ethyl)-carbamic acid tert-butyl ester (296252-54-5) → {2-benzyloxy-1-[3-(3-{1-[2-tert-butoxycarbonylamino-3-(4-fluoro-3-nitro-phenyl)-propionylamino]-2-hydroxy-ethyl}-5-methoxy-phenoxy)-4-methoxy-phenyl]-ethyl}-carbamic acid tert-butyl ester (331731-34-1)

Guidance literature:

With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N,N-dimethyl-formamide; at 0 ℃; for 6h;

DOI:10.1021/ja003835i

Reference yield:

3-hydroxy-5-methoxybenzaldehyde (57179-35-8) → {2-benzyloxy-1-[3-(3-{1-[2-tert-butoxycarbonylamino-3-(4-fluoro-3-nitro-phenyl)-propionylamino]-2-hydroxy-ethyl}-5-methoxy-phenoxy)-4-methoxy-phenyl]-ethyl}-carbamic acid tert-butyl ester (331731-34-1)

Guidance literature:

Multi-step reaction with 15 steps

1.1: 89 percent / K₂CO₃ / dimethylformamide / 3 h / 60 °C

2.1: 87 percent / tetrahydrofuran / 2 h / -78 - 25 °C

3.1: 78 percent / t-butyl hypochlorite; (DHQD)2PHAL; NaOH / K₂OsO₂(OH)4 / H₂O; propan-1-ol / 1 h / 25 °C

4.1: 95 percent / i-Pr₂NEt / CH₂Cl₂ / 20 h / 25 °C

5.1: H₂ / Pd/C / methanol / 3 h

6.1: 3.01 g / pyridine / CH₂Cl₂ / 3 h / 25 °C

7.1: 70 percent / K₂CO₃; 18-crown-6 / dimethylsulfoxide / 15 h / 25 °C

8.1: 100 percent / H₂ / Pd/C / methanol / 1 h

9.1: t-BuONO; HBF₄ / acetonitrile; H₂O / 0.33 h

9.2: 80 percent / Cu₂O; Cu(NO₃)2 / acetonitrile; H₂O / 1 h / 0 °C

10.1: 95 percent / K₂CO₃; Bu₄NI / dimethylformamide / 25 °C

11.1: 91 percent / NaH; Bu₄NI / dimethylformamide; tetrahydrofuran / 2 h / 0 °C

12.1: aq. HCl / ethyl acetate / 0.33 h / 0 °C

13.1: 0.341 g / NaHCO₃ / tetrahydrofuran; H₂O / 18 h

14.1: 96 percent / K₂CO₃; H₂O / methanol / 18 h / 25 °C

15.1: 72 percent / EDCI*HCl; HOBt; DMF / 6 h / 0 °C

With pyridine; hydrogenchloride; sodium hydroxide; tetrafluoroboric acid; tert.-butylnitrite; 18-crown-6 ether; tert-butylhypochlorite; water; hydrogen; tetra-(n-butyl)ammonium iodide; sodium hydride; sodium hydrogencarbonate; potassium carbonate; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; 1,4-bis(9-O-dihydroquinidine)phthalazine; N-ethyl-N,N-diisopropylamine; N,N-dimethyl-formamide; palladium on activated charcoal; potassium dioxotetrahydroxoosmate(VI); In tetrahydrofuran; methanol; propan-1-ol; dichloromethane; water; dimethyl sulfoxide; ethyl acetate; N,N-dimethyl-formamide; acetonitrile; 3.1: Sharpless asymmetric aminohydroxylation;

DOI:10.1021/ja003835i

Reference yield:

3-(benzyloxy)-5-methoxybenzaldehyde (50637-29-1) → {2-benzyloxy-1-[3-(3-{1-[2-tert-butoxycarbonylamino-3-(4-fluoro-3-nitro-phenyl)-propionylamino]-2-hydroxy-ethyl}-5-methoxy-phenoxy)-4-methoxy-phenyl]-ethyl}-carbamic acid tert-butyl ester (331731-34-1)

Guidance literature:

Multi-step reaction with 14 steps

1.1: 87 percent / tetrahydrofuran / 2 h / -78 - 25 °C

2.1: 78 percent / t-butyl hypochlorite; (DHQD)2PHAL; NaOH / K₂OsO₂(OH)4 / H₂O; propan-1-ol / 1 h / 25 °C

3.1: 95 percent / i-Pr₂NEt / CH₂Cl₂ / 20 h / 25 °C

4.1: H₂ / Pd/C / methanol / 3 h

5.1: 3.01 g / pyridine / CH₂Cl₂ / 3 h / 25 °C

6.1: 70 percent / K₂CO₃; 18-crown-6 / dimethylsulfoxide / 15 h / 25 °C

7.1: 100 percent / H₂ / Pd/C / methanol / 1 h

8.1: t-BuONO; HBF₄ / acetonitrile; H₂O / 0.33 h

8.2: 80 percent / Cu₂O; Cu(NO₃)2 / acetonitrile; H₂O / 1 h / 0 °C

9.1: 95 percent / K₂CO₃; Bu₄NI / dimethylformamide / 25 °C

10.1: 91 percent / NaH; Bu₄NI / dimethylformamide; tetrahydrofuran / 2 h / 0 °C

11.1: aq. HCl / ethyl acetate / 0.33 h / 0 °C

12.1: 0.341 g / NaHCO₃ / tetrahydrofuran; H₂O / 18 h

13.1: 96 percent / K₂CO₃; H₂O / methanol / 18 h / 25 °C

14.1: 72 percent / EDCI*HCl; HOBt; DMF / 6 h / 0 °C

With pyridine; hydrogenchloride; sodium hydroxide; tetrafluoroboric acid; tert.-butylnitrite; 18-crown-6 ether; tert-butylhypochlorite; water; hydrogen; tetra-(n-butyl)ammonium iodide; sodium hydride; sodium hydrogencarbonate; potassium carbonate; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; 1,4-bis(9-O-dihydroquinidine)phthalazine; N-ethyl-N,N-diisopropylamine; N,N-dimethyl-formamide; palladium on activated charcoal; potassium dioxotetrahydroxoosmate(VI); In tetrahydrofuran; methanol; propan-1-ol; dichloromethane; water; dimethyl sulfoxide; ethyl acetate; N,N-dimethyl-formamide; acetonitrile; 2.1: Sharpless asymmetric aminohydroxylation;

DOI:10.1021/ja003835i

upstream raw materials:

(R)-N-(tert-butoxycarbonyl)-4-fluoro-3-nitrophenylalanine

((R)-1-{3-[3-((S)-1-Amino-2-hydroxy-ethyl)-5-methoxy-phenoxy]-4-methoxy-phenyl}-2-benzyloxy-ethyl)-carbamic acid tert-butyl ester

di-tert-butyl dicarbonate

3-hydroxy-5-methoxybenzaldehyde

Downstream raw materials:

[1-({{3-[5-(2-benzyloxy-1-tert-butoxycarbonylamino-ethyl)-2-methoxy-phenoxy]-5-methoxy-phenyl}-[1-(3,5-dihydroxy-4-methoxy-phenyl)-2-hydroxy-ethylcarbamoyl]-methyl}-carbamoyl)-2-(4-fluoro-3-nitro-phenyl)-ethyl]-carbamic acid tert-butyl ester

{3-[5-(2-benzyloxy-1-tert-butoxycarbonylamino-ethyl)-2-methoxy-phenoxy]-5-methoxy-phenyl}-[2-tert-butoxycarbonylamino-3-(4-fluoro-3-nitro-phenyl)-propionylamino]-acetic acid