(2R,3R)-3-(N-(benzyloxycarbonyl)amino)-2-hydroxy-4-phenylbutanoic acid methyl ester

Base Information

• Chemical Name: (2R,3R)-3-(N-(benzyloxycarbonyl)amino)-2-hydroxy-4-phenylbutanoic acid methyl ester
• CAS No.: 124782-06-5
• Molecular Formula: C₁₉H₂₁NO₅
• Molecular Weight: 343.379
• Mol file: 124782-06-5.mol

Synonyms:(2R,3R)-3-(N-(benzyloxycarbonyl)amino)-2-hydroxy-4-phenylbutanoic acid methyl ester

Chemical Property of (2R,3R)-3-(N-(benzyloxycarbonyl)amino)-2-hydroxy-4-phenylbutanoic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3R)-3-(N-(benzyloxycarbonyl)amino)-2-hydroxy-4-phenylbutanoic acid methyl ester

There total 6 articles about (2R,3R)-3-(N-(benzyloxycarbonyl)amino)-2-hydroxy-4-phenylbutanoic acid methyl 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: 88.0%

(2R,3R)-3-Benzyloxycarbonylamino-2-(tert-butyl-dimethyl-silanyloxy)-4-phenyl-butyric acid methyl ester → (2R,3R)-3-(N-(benzyloxycarbonyl)amino)-2-hydroxy-4-phenylbutanoic acid methyl ester (124782-06-5)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 0 ℃; for 0.5h;

DOI:10.1016/S0040-4039(01)00120-4

Reference yield: 85.0%

benzyl chloroformate (501-53-1,94274-21-2) + methyl (2R,3R)-3-amino-2-hydroxy-4-phenylbutanoate hydrochloride → (2R,3R)-3-(N-(benzyloxycarbonyl)amino)-2-hydroxy-4-phenylbutanoic acid methyl ester (124782-06-5)

Guidance literature:

With sodium hydrogencarbonate; In water; ethyl acetate; at 25 ℃; for 17h;

DOI:10.1271/bbb.63.1304

Reference yield:

(4S,5R)-4-methoxycarbonylmethyl-5-phenyloxazolidin-2-one (178897-35-3) → (2R,3R)-3-(N-(benzyloxycarbonyl)amino)-2-hydroxy-4-phenylbutanoic acid methyl ester (124782-06-5)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 83 percent / Ag₂CO₃ / toluene / 6 h / 60 °C

2.1: LiHMDS / tetrahydrofuran / 1 h / -78 °C

2.2: 1.95 g / 3-phenyl-2-(phenylsulfonyl)oxaziridine / tetrahydrofuran / 1 h / -78 °C

3.1: 86 percent / H₂; HCl / Pd/C / H₂O; dioxane / 4 h / 25 °C / 2574.28 Torr

4.1: 85 percent / NaHCO₃ / H₂O; ethyl acetate / 17 h / 25 °C

With hydrogenchloride; hydrogen; sodium hydrogencarbonate; silver carbonate; lithium hexamethyldisilazane; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; water; ethyl acetate; toluene; 1.1: Alkylation / 2.1: Metallation / 2.2: Oxidation / 3.1: Hydrogenolysis / 4.1: Condensation;

DOI:10.1271/bbb.63.1304

upstream raw materials:

benzyl chloroformate

(4S,5R)-4-methoxycarbonylmethyl-5-phenyloxazolidin-2-one

methyl (4S,5R)-2-benzyloxy-5-phenyloxazoline-4-acetate

(R)-((4S,5R)-2-Benzyloxy-5-phenyl-4,5-dihydro-oxazol-4-yl)-hydroxy-acetic acid methyl ester

Downstream raw materials:

methyl (2S,3R)-3-(benzyloxycarbonyl)amino-2-formyloxy-4-phenylbutanoate

Aminodeoxybestatin

(2S,3R)-2-Azido-3-(benzyloxycarbonylamino)-4-phenylbutanoic Acid Methyl Ester

(2S,3R)-2-Azido-3-(benzyloxycarbonylamino)-4-phenylbutanoic Acid