(1R,2R)-1-((tert-butoxycarbonyl)amino)-3-methoxy-1-(4-methoxyphenyl)-3-oxopropan-2-yl 4-nitrobenzoate

Base Information

• Chemical Name: (1R,2R)-1-((tert-butoxycarbonyl)amino)-3-methoxy-1-(4-methoxyphenyl)-3-oxopropan-2-yl 4-nitrobenzoate
• CAS No.: 929517-39-5
• Molecular Formula: C₂₃H₂₆N₂O₉
• Molecular Weight: 474.467
• Mol file: 929517-39-5.mol

Synonyms:(1R,2R)-1-((tert-butoxycarbonyl)amino)-3-methoxy-1-(4-methoxyphenyl)-3-oxopropan-2-yl 4-nitrobenzoate

Chemical Property of (1R,2R)-1-((tert-butoxycarbonyl)amino)-3-methoxy-1-(4-methoxyphenyl)-3-oxopropan-2-yl 4-nitrobenzoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,2R)-1-((tert-butoxycarbonyl)amino)-3-methoxy-1-(4-methoxyphenyl)-3-oxopropan-2-yl 4-nitrobenzoate

There total 9 articles about (1R,2R)-1-((tert-butoxycarbonyl)amino)-3-methoxy-1-(4-methoxyphenyl)-3-oxopropan-2-yl 4-nitrobenzoate 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: 73.0%

methyl (2S,3R)-3-((tert-butoxycarbonyl)amino)-2-hydroxy-3-(4-methoxyphenyl)propanoate (929517-34-0) + 4-nitro-benzoic acid (62-23-7) → (1R,2R)-1-((tert-butoxycarbonyl)amino)-3-methoxy-1-(4-methoxyphenyl)-3-oxopropan-2-yl 4-nitrobenzoate (929517-39-5)

Guidance literature:

With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; at 0 - 20 ℃; for 16h; Darkness;

DOI:10.1039/d1ob01062j

Reference yield:

(3S,4R)-3-hydroxy-4-(4-methoxyphenyl)-1-[(R)-1-(4-methoxyphenyl)ethyl]azetidin-2-one (929517-32-8) → (1R,2R)-1-((tert-butoxycarbonyl)amino)-3-methoxy-1-(4-methoxyphenyl)-3-oxopropan-2-yl 4-nitrobenzoate (929517-39-5)

Guidance literature:

Multi-step reaction with 4 steps

1: 92 percent / chlorotrimethylsilane / 5 h / Heating

2: hydrogen / Pd(OH)2/C / methanol / 12 h / 23 °C

3: 0.72 g / NaHCO₃ / methanol / 6 h / 23 °C / sonication

4: 70 percent / PPh₃; DIAD / tetrahydrofuran / 6 h / 23 °C

With chloro-trimethyl-silane; di-isopropyl azodicarboxylate; hydrogen; sodium hydrogencarbonate; triphenylphosphine; palladium dihydroxide; In tetrahydrofuran; methanol;

DOI:10.1021/ol062752p

Reference yield:

(E)-(R)-N-(4-methoxybenzylidene)-1-(4-methoxyphenyl)ethanamine (929517-37-3) → (1R,2R)-1-((tert-butoxycarbonyl)amino)-3-methoxy-1-(4-methoxyphenyl)-3-oxopropan-2-yl 4-nitrobenzoate (929517-39-5)

Guidance literature:

Multi-step reaction with 6 steps

1: 80 percent / triethylamine / CH₂Cl₂ / 12 h / 20 °C

2: 58 percent / KOH / tetrahydrofuran; H₂O / 2 h / 0 °C

3: 92 percent / chlorotrimethylsilane / 5 h / Heating

4: hydrogen / Pd(OH)2/C / methanol / 12 h / 23 °C

5: 0.72 g / NaHCO₃ / methanol / 6 h / 23 °C / sonication

6: 70 percent / PPh₃; DIAD / tetrahydrofuran / 6 h / 23 °C

With potassium hydroxide; chloro-trimethyl-silane; di-isopropyl azodicarboxylate; hydrogen; sodium hydrogencarbonate; triethylamine; triphenylphosphine; palladium dihydroxide; In tetrahydrofuran; methanol; dichloromethane; water; 1: Staudinger reaction;

DOI:10.1021/ol062752p

upstream raw materials:

methyl (2S,3R)-3-((tert-butoxycarbonyl)amino)-2-hydroxy-3-(4-methoxyphenyl)propanoate

4-nitro-benzoic acid

(E)-(R)-N-(4-methoxybenzylidene)-1-(4-methoxyphenyl)ethanamine

(3S,4R)-3-hydroxy-4-(4-methoxyphenyl)-1-[(R)-1-(4-methoxyphenyl)ethyl]azetidin-2-one

Downstream raw materials:

(2R,3R)-methyl 3-[N-(tert-butoxycarbonyl)amino]-2-hydroxy-3-(p-methoxyphenyl)propanoate

(4R,5R)-cytoxazone

(2R,3R)-3-tert-butoxycarbonylamino-3-(4-methoxyphenyl)-1,2-propanediol