(2R,3S)-3-Cbz-amino-2-hydroxy-4-phenyl-1-(N-benzylacetamido)butane

Base Information

• Chemical Name: (2R,3S)-3-Cbz-amino-2-hydroxy-4-phenyl-1-(N-benzylacetamido)butane
• CAS No.: 1190630-69-3
• Molecular Formula: C₂₇H₃₀N₂O₄
• Molecular Weight: 446.546
• Mol file: 1190630-69-3.mol

Synonyms:(2R,3S)-3-Cbz-amino-2-hydroxy-4-phenyl-1-(N-benzylacetamido)butane

Chemical Property of (2R,3S)-3-Cbz-amino-2-hydroxy-4-phenyl-1-(N-benzylacetamido)butane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3S)-3-Cbz-amino-2-hydroxy-4-phenyl-1-(N-benzylacetamido)butane

There total 10 articles about (2R,3S)-3-Cbz-amino-2-hydroxy-4-phenyl-1-(N-benzylacetamido)butane 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: 75.0%

acetic anhydride (108-24-7) + (2R,3S)-3-Cbz-amino-2-hydroxy-4-phenyl-1-benzylaminobutane (143224-83-3) → (2R,3S)-3-Cbz-amino-2-hydroxy-4-phenyl-1-(N-benzylacetamido)butane (1190630-69-3)

Guidance literature:

With dmap; triethylamine; In tetrahydrofuran; for 6h;

DOI:10.1021/ml300197h

Reference yield:

[(2R,3S)-3-azido-4-phenyl-2-(tetrahydropyran-2-yloxy)butyl]benzylamine (1190630-74-0) → (2R,3S)-3-Cbz-amino-2-hydroxy-4-phenyl-1-(N-benzylacetamido)butane (1190630-69-3)

Guidance literature:

Multi-step reaction with 4 steps

1: palladium on activated charcoal; hydrogen / methanol / 12 h

2: sodium hydrogencarbonate / diethyl ether; water / 5 h / 0 °C

3: pyridinium p-toluenesulfonate / ethanol / 5 h / 60 °C

4: triethylamine; dmap / tetrahydrofuran / 6 h

With dmap; palladium on activated charcoal; hydrogen; pyridinium p-toluenesulfonate; sodium hydrogencarbonate; triethylamine; In tetrahydrofuran; methanol; diethyl ether; ethanol; water;

DOI:10.1021/ml300197h

Reference yield:

[(1S,2R)-1-benzyl-3-benzylamino-2-(tetrahydropyran-2-yloxy)propyl]carbamic acid benzyl ester (1190630-76-2) → (2R,3S)-3-Cbz-amino-2-hydroxy-4-phenyl-1-(N-benzylacetamido)butane (1190630-69-3)

Guidance literature:

Multi-step reaction with 2 steps

1: pyridinium p-toluenesulfonate / ethanol / 5 h / 60 °C

2: triethylamine; dmap / tetrahydrofuran / 6 h

With dmap; pyridinium p-toluenesulfonate; triethylamine; In tetrahydrofuran; ethanol;

DOI:10.1021/ml300197h

upstream raw materials:

acetic anhydride

(2R,3S)-3-Cbz-amino-2-hydroxy-4-phenyl-1-benzylaminobutane

3(S)-azido-4-phenyl-1-(p-toluenesulphonyloxy)-2(S)-butanol

(2R,3S)-3-amino-2-tetrahydropyranyloxy-4-phenyl-1-benzylaminobutane