145432-51-5

Basic information

• Product Name: (2S,3R)-N-BOC-2-AMINO-3-PHENYLBUTYRIC ACID, 95%, (98% E.E.)
• Synonyms: (2S,3R)-N-BOC-2-AMINO-3-PHENYLBUTYRIC ACID, 95%, (98% E.E.);(2S,3R)-N-BOC-beta-methylphenylalanine;N-BOC-threo-L-beta-methylphenylalanine;(βR)-N-(tert-butoxycarbonyl)-β-methyl-L-phenylalanine;(2S,3R)-N-(Tert-Butoxy)Carbonyl 2-Amino-3-phenylbutyric acid
• CAS NO: 145432-51-5
• Molecular Formula: C₁₅H₂₁NO₄
• Molecular Weight: 279.33154
• Mol File: 145432-51-5.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 422.1°C (rough estimate)
• Appearance: /
• Density: 1.1083 (rough estimate)
• Refractive Index: 1.5130 (estimate)
• PKA: 3.90±0.10(Predicted)
• CAS DataBase Reference: (2S,3R)-N-BOC-2-AMINO-3-PHENYLBUTYRIC ACID, 95%, (98% E.E.)(CAS DataBase Reference)
• NIST Chemistry Reference: (2S,3R)-N-BOC-2-AMINO-3-PHENYLBUTYRIC ACID, 95%, (98% E.E.)(145432-51-5)
• EPA Substance Registry System: (2S,3R)-N-BOC-2-AMINO-3-PHENYLBUTYRIC ACID, 95%, (98% E.E.)(145432-51-5)

Safety Data

• Hazardous Substances Data: 145432-51-5(Hazardous Substances Data)

Usage

Description

(2S,3R)-N-BOC-2-AMINO-3-PHENYLBUTYRIC ACID, 95%, (98% E.E.) is a chiral compound with a specific stereochemistry, characterized by the 2S,3R configuration. It is a derivative of amino acids, featuring a BOC (tert-butoxycarbonyl) protecting group, which is commonly used in peptide synthesis to protect the amino group. (2S,3R)-N-BOC-2-AMINO-3-PHENYLBUTYRIC ACID, 95%, (98% E.E.) is typically obtained with a purity of 95% and an enantiomeric excess (E.E.) of 98%, indicating a high level of stereochemical purity.

Uses

Used in Pharmaceutical Industry:
(2S,3R)-N-BOC-2-AMINO-3-PHENYLBUTYRIC ACID, 95%, (98% E.E.) is used as a reagent for the preparation of peptide HTI-286 analogs, which possess potential anticancer properties. The compound plays a crucial role in the synthesis of these therapeutic peptides, contributing to the development of novel cancer treatments.

Upstream product

• 1070-19-5 N-(tert-butyloxycarbonyl) azide 
• 25488-27-1 threo-L-(2S,3R)-β-methylphenylalanine 
• 197714-18-4 methyl (2S,3R)-2-[(tert-butoxycarbonyl)amino]-3-phenylbutanoate 
• 24424-99-5 di-tert-butyl dicarbonate 
• 59850-51-0 threo-(+)-(2S,3R)-L-β-Methylphenylalanine hydrochloride 
• 4610-69-9 (Z)-ethyl cinnamate 
• 104196-23-8 (2S,3S)-2,3-epoxy-3-phenyl-1-propanol 
• 126060-73-9 ethyl (2R,3R)-3-phenyl-2,3-oxiranepropanoate 
• 121840-97-9 (2R,3R)-3-phenyl-butane-1,2-diol 
• 91828-71-6 (2R,3R)-2-Hydroxy-3-phenylbutyric acid methyl ester 
• 99528-64-0 cis-2,3-epoxy-3-phenyl-1-propanoic acid 
• 197714-12-8 (2R,3R)-2-(methanesulfonyloxy)-3-phenyl-1-butanol 
• 197714-07-1 methyl (2R,3R)-2-(methanesulfonyloxy)-3-phenylbutanoate 
• 197714-08-2 (2R,3R)-1-[(tert-butyldimethylsilyl)oxy]-3-phenyl-2-butanol 

Downstream Products

• 90731-58-1 BOC-βPhabu-Arg(NO2)-OBZL(NO2) 
• 90731-63-8 Gly-(Cl)Phe-Ser-Pro-βPhabu-Arg(NO2)-OBZL(NO2). Trifluoracetat 
• 90740-78-6 BOC-Pro-βPhabu-Arg(NO2)-OBZL(NO2) 
• 90731-59-2 βPhabu-Arg(NO2)-OBZL(NO2). Hydrochlorid 
• 90731-61-6 Pro-βPhabu-Arg(NO2)-OBZL(NO2). Trifluoracetat 
• 90731-62-7 BOC-Gly-(Cl)Phe-Ser-Pro-βPhabu-Arg(NO2)-OBZL(NO2) 
• 946089-56-1 C₂₅H₃₂N₂O₇ 

Relevant articles and documents

Stereoselective Synthesis of β-Branched Aromatic α-Amino Acids by Biocatalytic Dynamic Kinetic Resolution**

β-Branched noncanonical amino acids are valuable molecules in modern drug development efforts. However, they are still challenging to prepare due to the need to set multiple stereocenters in a stereoselective fashion, and contemporary methods for the synthesis of such compounds often rely on the use of rare-transition-metal catalysts with designer ligands. Herein, we report a highly diastereo- and enantioselective biocatalytic transamination method to prepare a broad range of aromatic β-branched α-amino acids. Mechanistic studies show that the transformation proceeds through dynamic kinetic resolution that is unique to the optimal enzyme. To highlight its utility and practicality, the biocatalytic reaction was applied to the synthesis of several sp3-rich cyclic fragments and the first total synthesis of jomthonic acid A.

SUBSTITUTED HYDANTOINS

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A Catalytic Asymmetric Synthesis of N-Boc-β-Methylphenylalanines

An efficient, stereodivergent, and enantioselective synthesis of the syn and anti diastereomers of N-Boc-β-methylphenylalanine has been developed. Starting from enantiomerically pure (2S,3S)-2,3-epoxy-3-phenyl-1-propanol, a three-step sequence, consisting of the oxidation of the primary alcohol up to the carboxyl stage, ring opening of the epoxy acid with Me2CuCNLi2, and esterification of the resulting hydroxy acid with methyl iodide, leads to the hydroxy ester anti-W, which has been converted in a stereodivergent manner into both the (2S,3R) and the (2R,3R) diastereomers of N-Boc-β-methylphenylalanine, syn-1 and anti-1, respectively. Activation of the secondary hydroxy group in anti-10 as a mesylate, followed by nucleophilic displacement with sodium azide, hydrogenolysis with simultaneous protection of the amino group, and saponification with LiOH, affords syn-1. The same reaction sequence applied to syn-10, obtained in turn by Mitsunobu reaction of anti-10 with p-nitrobenzoic acid followed by the hydrolysis of the resulting p-nitrobenzoate, leads to anti-1. Both products have been obtained with ≥99% enantiomeric excess.