(2S,3R)-N-BOC-2-AMINO-3-PHENYLBUTYRIC ACID, 95%, (98% E.E.)

Base Information

• Chemical Name: (2S,3R)-N-BOC-2-AMINO-3-PHENYLBUTYRIC ACID, 95%, (98% E.E.)
• CAS No.: 145432-51-5
• Molecular Formula: C15H21 N O4
• Molecular Weight: 279.336
• Mol file: 145432-51-5.mol

Synonyms:L-Phenylalanine,N-[(1,1-dimethylethoxy)carbonyl]-b-methyl-, threo-; (2S,3R)-2-(tert-Butoxycarbonylamino)-3-phenylbutanoicacid

Chemical Property of (2S,3R)-N-BOC-2-AMINO-3-PHENYLBUTYRIC ACID, 95%, (98% E.E.)

Chemical Property:

• Refractive Index: 1.5130 (estimate)
• Boiling Point: 422.1°C (rough estimate)
• PKA: 3.90±0.10(Predicted)
• PSA: 75.63000
• Density: 1.1083 (rough estimate)
• LogP: 3.15890

Purity/Quality:

98%min ^*data from raw suppliers

(2R,3R)-N-BOC-2-Amino-3-phenyl-butyricAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: (2R,3R)-N-BOC-2-Amino-3-phenyl-butyric Acid is a reagent used for preparation of petide HTI-286 analogs, which potential anticancer properties.

Technology Process of (2S,3R)-N-BOC-2-AMINO-3-PHENYLBUTYRIC ACID, 95%, (98% E.E.)

There total 26 articles about (2S,3R)-N-BOC-2-AMINO-3-PHENYLBUTYRIC ACID, 95%, (98% E.E.) 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: 100.0%

methyl (2S,3R)-2-[(tert-butoxycarbonyl)amino]-3-phenylbutanoate (197714-18-4) → (βR)-N-(tert-butoxycarbonyl)-β-methyl-L-phenylalanine (145432-51-5,630424-76-9)

Guidance literature:

With lithium hydroxide; In tetrahydrofuran; at 70 ℃; for 1h;

DOI:10.1021/jo971178f

Reference yield: 90.0%

[(1S,2R)-1-((S)-2-oxo-4-phenyl-oxazolidine-3-carbonyl)-2-phenyl-propyl]-carbamic acid tert-butyl ester (876756-07-9) → (βR)-N-(tert-butoxycarbonyl)-β-methyl-L-phenylalanine (145432-51-5,630424-76-9)

Guidance literature:

[(1S,2R)-1-((S)-2-oxo-4-phenyl-oxazolidine-3-carbonyl)-2-phenyl-propyl]-carbamic acid tert-butyl ester; With lithium hydroxide; dihydrogen peroxide; In tetrahydrofuran; water; at 20 ℃;

With sodium sulfite; In tetrahydrofuran; water; for 1h;

With citric acid; In tetrahydrofuran; dichloromethane; water;

Reference yield: 82.0%

di-tert-butyl dicarbonate (24424-99-5) + threo-(+)-(2S,3R)-L-β-Methylphenylalanine hydrochloride (59850-51-0) → (βR)-N-(tert-butoxycarbonyl)-β-methyl-L-phenylalanine (145432-51-5,630424-76-9)

Guidance literature:

With sodium hydroxide; In acetone; for 15h;

DOI:10.1002/chem.200400977

upstream raw materials:

N-(tert-butyloxycarbonyl) azide

threo-L-(2S,3R)-β-methylphenylalanine

methyl (2S,3R)-2-[(tert-butoxycarbonyl)amino]-3-phenylbutanoate

di-tert-butyl dicarbonate

Downstream raw materials:

BOC-βPhabu-Arg(NO2)-OBZL(NO2)

C₂₅H₃₂N₂O₇

BOC-Gly-(Cl)Phe-Ser-Pro-βPhabu-Arg(NO2)-OBZL(NO2)

Pro-βPhabu-Arg(NO2)-OBZL(NO2). Trifluoracetat

Refernces

• 1、 Wang, Bo,Liu, Yunpeng,Jiao, Rui,Feng, Yiqing,Li, Qiong,Chen, Chen,Liu, Long,He, Gang,Chen, Gong. "Total Synthesis of Mannopeptimycins α and β". supporting information. p. 3926 - 3932. Retrieved 2016/04/09.
• 2、 Reinscheid, Uwe M.,Zlatopolskiy, Boris D.,Griesinger, Christian,Zeeck, Axel,De Meijere, Armin. "The structure of hormaomycin and one of its all-peptide aza- analogues in solution: Syntheses and biological activities of new hormaomycin analogues". . p. 2929 - 2945. Retrieved 2007/10/03.