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

Base Information

• Chemical Name: (2R,3R)-methyl 3-[N-(tert-butoxycarbonyl)amino]-2-hydroxy-3-(p-methoxyphenyl)propanoate
• CAS No.: 929517-35-1
• Molecular Formula: C₁₆H₂₃NO₆
• Molecular Weight: 325.362
• Mol file: 929517-35-1.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 13 articles about (2R,3R)-methyl 3-[N-(tert-butoxycarbonyl)amino]-2-hydroxy-3-(p-methoxyphenyl)propanoate 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: 98.0%

(1R,2R)-1-((tert-butoxycarbonyl)amino)-3-methoxy-1-(4-methoxyphenyl)-3-oxopropan-2-yl 4-nitrobenzoate (929517-39-5) → (2R,3R)-methyl 3-[N-(tert-butoxycarbonyl)amino]-2-hydroxy-3-(p-methoxyphenyl)propanoate (929517-35-1)

Guidance literature:

With triethylamine; In tetrahydrofuran; at 23 ℃; for 1h;

DOI:10.1021/ol062752p

Reference yield: 69.0%

(2R,3R)-methyl 3-[N-(tert-butoxycarbonyl)amino]-3-(p-methoxyphenyl)-2-[(2,2,6,6-tetramethylpiperidin-1-yl)oxy]propanoate → (2R,3R)-methyl 3-[N-(tert-butoxycarbonyl)amino]-2-hydroxy-3-(p-methoxyphenyl)propanoate (929517-35-1)

Guidance literature:

With acetic acid; zinc; In tetrahydrofuran; water; at 70 ℃; for 4h; Inert atmosphere;

DOI:10.1002/ejoc.201801139

Reference yield:

(E)-(R)-N-(4-methoxybenzylidene)-1-(4-methoxyphenyl)ethanamine (929517-37-3) → (2R,3R)-methyl 3-[N-(tert-butoxycarbonyl)amino]-2-hydroxy-3-(p-methoxyphenyl)propanoate (929517-35-1)

Guidance literature:

Multi-step reaction with 7 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

7: 98 percent / triethylamine / tetrahydrofuran / 1 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:

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

(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

methyl (2S,3R)-2-hydroxy-3-(4-methoxyphenyl)-3-[((R)-1-(4-methoxyphenyl)ethyl)amino]propionate

Downstream raw materials:

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

(4R,5R)-cytoxazone