((R)-1-((S)-2-benzamido-3-phenylpropanamido)-3-methylbutyl)boronic Acid

Base Information

• Chemical Name: ((R)-1-((S)-2-benzamido-3-phenylpropanamido)-3-methylbutyl)boronic Acid
• CAS No.: 179324-79-9
• Molecular Formula: C₂₁H₂₇BN₂O₄
• Molecular Weight: 382.267
• Mol file: 179324-79-9.mol

Synonyms:((R)-1-((S)-2-benzamido-3-phenylpropanamido)-3-methylbutyl)boronic Acid

Chemical Property of ((R)-1-((S)-2-benzamido-3-phenylpropanamido)-3-methylbutyl)boronic Acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ((R)-1-((S)-2-benzamido-3-phenylpropanamido)-3-methylbutyl)boronic Acid

There total 16 articles about ((R)-1-((S)-2-benzamido-3-phenylpropanamido)-3-methylbutyl)boronic Acid 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: 40.5%

(1S,3R,5S)-pinanediol-N-(phenyl)carbonyl-β-(1-phenyl)-L-alanine-L-leucineboronate → ((R)-1-((S)-2-benzamido-3-phenylpropanamido)-3-methylbutyl)boronic Acid (179324-79-9)

Guidance literature:

With hydrogenchloride; Dihydroxy-isobutyl-boran; water; In methanol; n-heptane; at 20 - 25 ℃;

Reference yield:

N-((S)-1-(((R)-3-methyl-1-((3aR,4R,6R,7aS)-5,5,7a-trimethylhexahydro-4,6-methanobenzo[d][1,3,2]dioxaborol-2-yl)butyl)amino)-1-oxo-3-phenylpropan-2-yl)benzamide (1621908-76-6) → ((R)-1-((S)-2-benzamido-3-phenylpropanamido)-3-methylbutyl)boronic Acid (179324-79-9)

Guidance literature:

N-((S)-1-(((R)-3-methyl-1-((3aR,4R,6R,7aS)-5,5,7a-trimethylhexahydro-4,6-methanobenzo[d][1,3,2]dioxaborol-2-yl)butyl)amino)-1-oxo-3-phenylpropan-2-yl)benzamide; With potassium hydrogen bifluoride; In methanol; at 20 ℃; for 4h;

With silica gel; In water; at 20 ℃; for 5h;

DOI:10.3390/molecules181215398

Reference yield:

L-phenylalanine (63-91-2,25191-15-5,658-69-5,67675-33-6) → ((R)-1-((S)-2-benzamido-3-phenylpropanamido)-3-methylbutyl)boronic Acid (179324-79-9)

Guidance literature:

Multi-step reaction with 5 steps

1.1: sodium hydroxide / water; acetone / 18 h / 20 °C / pH 7.5 - 8

2.1: O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate / dichloromethane / 0.08 h / 20 °C / Inert atmosphere

2.2: -2 - 0 °C

3.1: hydrogenchloride / ethyl acetate / 4 h / 10 - 15 °C

4.1: O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate / dichloromethane / 0.33 h / Inert atmosphere

4.2: 0 - 20 °C

5.1: hydrogenchloride; water; Dihydroxy-isobutyl-boran / methanol; n-heptane / 20 - 25 °C

With hydrogenchloride; Dihydroxy-isobutyl-boran; water; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; sodium hydroxide; In methanol; n-heptane; dichloromethane; water; ethyl acetate; acetone;

upstream raw materials:

N-{(1S)-3-methyl-1-[(3aS,4S,6S,7aS)-3a,5,5-trimethylhexahydro-4,6-methano-1,3,2-benzodioxaborol-2-yl]butyl}phenylalanine amide

N-Cbz-L-Phe

L-phenylalanine

N-tert-butoxycarbonyl-L-phenylalanine

Refernces

• 1、 Peuchmaur, Marine,Lacour, Marie-Agnes,Sevalle, Jean,Lisowski, Vincent,Touati-Jallabe, Youness,Rodier, Fabien,Martinez, Jean,Checler, Frederic,Hernandez, Jean-Francois. "Further characterization of a putative serine protease contributing to the γ-secretase cleavage of β-amyloid precursor protein". . p. 1018 - 1029. Retrieved 2013/03/14.