(2R,3S)-N-(tert-butoxycarbonyl)-3-amino-2-hydroxy-4-phenylbutanoic acid methyl ester

Base Information

• Chemical Name: (2R,3S)-N-(tert-butoxycarbonyl)-3-amino-2-hydroxy-4-phenylbutanoic acid methyl ester
• CAS No.: 116565-10-7
• Molecular Formula: C₁₆H₂₃NO₅
• Molecular Weight: 309.362
• Mol file: 116565-10-7.mol

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

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

There total 36 articles about (2R,3S)-N-(tert-butoxycarbonyl)-3-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: 97.0%

(2R,3S)-3-tert-butoxycarbonylamino-2-hydroxy-4-phenylbutyric acid (105181-72-4) + methyl iodide (74-88-4) → (2R,3S)-N-(tert-butoxycarbonyl)-3-amino-2-hydroxy-4-phenylbutanoic acid methyl ester (116565-10-7)

Guidance literature:

With potassium carbonate; In N,N-dimethyl-formamide; at 20 ℃; for 10h;

DOI:10.1248/cpb.51.702

Reference yield: 80.0%

di-tert-butyl dicarbonate (24424-99-5) + methyl 3-azido-2,4-dihydroxy-4-phenyl-(2R,3S,4R)-butanoate (591721-45-8) → (2R,3S)-N-(tert-butoxycarbonyl)-3-amino-2-hydroxy-4-phenylbutanoic acid methyl ester (116565-10-7)

Guidance literature:

With hydrogen; palladium dihydroxide; In methanol; at 20 ℃; for 12h;

DOI:10.1016/S0957-4166(03)00239-8

Reference yield: 25.0%

methanol (67-56-1) + tert-butyl (S)-(4-cyano-3-oxo-1-phenyl-4-(triphenyl-λ5-phosphanylidene)butan-2-yl)carbamate → N-(tert-butyloxycarbonyl)-(2S,3S)-3-amino-2-hydroxy-4-phenylbutanoic acid methyl ester (116565-03-8) + (2R,3S)-N-(tert-butoxycarbonyl)-3-amino-2-hydroxy-4-phenylbutanoic acid methyl ester (116565-10-7)

Guidance literature:

tert-butyl (S)-(4-cyano-3-oxo-1-phenyl-4-(triphenyl-λ⁵-phosphanylidene)butan-2-yl)carbamate; With ozone; In dichloromethane; at -78 ℃; Inert atmosphere;

methanol; With sodium tetrahydroborate; In dichloromethane; at -78 - 20 ℃; Inert atmosphere;

DOI:10.1007/s00044-020-02678-2

upstream raw materials:

3(S)-(N-tert-butoxycarbonylamino)-2(R,S)-hydroxy-4-phenylbutyric acid

methyl iodide

(2R,3S)-3-tert-Butoxycarbonylamino-4-phenyl-2-triisopropylsilanyloxy-butyric acid methyl ester

di-tert-butyl dicarbonate

Downstream raw materials:

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

(4S,5R)-4-Benzyl-2,2-dimethyl-oxazolidine-3,5-dicarboxylic acid 3-tert-butyl ester 5-methyl ester

((1S,2R)-1-benzyl-2,3-dihydroxypropyl)carbamic acid tert-butyl ester

(2R,3S)-3-tert-butoxycarbonylamino-2-hydroxy-4-phenylbutyric acid