72155-46-5

Basic information

• Product Name: (3S,4S)-4-T-BUTYLOXYCARBONYLAMINO-3-HYDROXY-5-PHENYL-PENTANOIC ACID
• Synonyms: (3S,4S)-4-T-BUTYLOXYCARBONYLAMINO-3-HYDROXY-5-PHENYL-PENTANOIC ACID;NALPHA-tert-Butoxycarbonyl-(3S,4S)-4-amino-3-hydroxy-5-phenylpentanoic acid
• CAS NO: 72155-46-5
• Molecular Formula: C₁₈H₂₇NO₅
• Molecular Weight: 309.35752
• Product Categories: Amino Acids
• Mol File: 72155-46-5.mol
• Article Data: 20

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (3S,4S)-4-T-BUTYLOXYCARBONYLAMINO-3-HYDROXY-5-PHENYL-PENTANOIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: (3S,4S)-4-T-BUTYLOXYCARBONYLAMINO-3-HYDROXY-5-PHENYL-PENTANOIC ACID(72155-46-5)
• EPA Substance Registry System: (3S,4S)-4-T-BUTYLOXYCARBONYLAMINO-3-HYDROXY-5-PHENYL-PENTANOIC ACID(72155-46-5)

Safety Data

• Hazardous Substances Data: 72155-46-5(Hazardous Substances Data)

Usage

General Description

(3S,4S)-4-T-BUTYLOXYCARRYLAMINO-3-HYDROXY-5-PHENYL-PENTANOIC ACID, also known as Boc-phenylalanine, is a chemical compound consisting of a pentanoic acid backbone with a phenyl group and an amino acid functional group. It is commonly used in the synthesis of peptides and as a building block in the creation of complex organic molecules. The "Boc" group in its name refers to the tert-butoxycarbonyl protecting group, which helps to prevent unwanted reactions during peptide synthesis. Boc-phenylalanine is often utilized in the pharmaceutical and biotechnology industries for the production of various drugs and research compounds.

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 18295-66-4 1-ethoxy-1-(trimethylsiloxy)ethene 
• 72155-45-4 Boc-L-phenylalaninal 
• 141-78-6 ethyl acetate 
• 194851-70-2 (S)-4-tert-Butoxycarbonylamino-3-hydroxy-6-methyl-heptanoic acid ethyl ester 
• 51987-73-6 (S)-2-tert-butoxycarbonylamino-3-phenyl-propionic acid methyl ester 
• 142955-51-9 N-butoxycarbonyl-L-phenylalanine anhydride 
• 13734-34-4 N-tert-butoxycarbonyl-L-phenylalanine 
• 220931-41-9 (S)-4-Benzyl-5-[1-ethoxycarbonyl-meth-(E)-ylidene]-oxazolidine-3-carboxylic acid benzyl ester 
• 55740-07-3 (4S)-4-benzyl-5-oxo-1,3-oxazolidine-3-carboxylic acid benzyl ester 
• 236747-30-1 4-(tert-butoxycarbonyl-methyl-amino)-3-oxo-5-phenyl-pentanoic acid ethyl ester 
• 64-17-5 ethanol 
• 172034-33-2 [(S)-1-((R)-3,3-Dichloro-4-oxo-oxetan-2-yl)-2-phenyl-ethyl]-carbamic acid tert-butyl ester 
• 58521-44-1 (4S)-4-<(tert-butyloxycarbonyl)amino>-6-methyl-3-oxoheptanoic acid ethyl ester 

Downstream Products

• 120742-17-8 ethyl (3S,4S)-3-hydroxy-4-amino-5-phenylpentanoate hydrochloride 
• 1309250-86-9 (3S,4S)-4-((3S,4S)-4-((3S,4S)-4-amino-3-hydroxy-6-methylheptanoylamino)-5-cyclohexyl-3-hydroxypentanoylamino)-3-hydroxy-5-phenylpentanoic acid ethyl ester hydrochloride 
• 116326-39-7 ES-6864 
• 119379-17-8 (3S,4S)-4-amino-5-cyclohexyl-3-hydroxy-N-(2-morpholinoethyl)pentanamide 
• 119357-93-6 (3S,4S)-4-((S)-2-Amino-3-thiazol-4-yl-propionylamino)-5-cyclohexyl-3-hydroxy-pentanoic acid (2-morpholin-4-yl-ethyl)-amide 
• 124278-64-4 (3S,4S)-4-(N-tert-butoxycarbonyl)amino-5-cyclohexyl-3-hydroxy-N-(2-morpholinoethyl)pentanamide 
• 98105-45-4 (3S,4S)-4-(N-tert-butoxycarbonyl)amino-5-cyclohexyl-3-hydroxypentanoic acid 
• 124278-65-5 (S,S)-γ-amino-β-hydroxy-N-<2-(4-morpholinyl)ethyl>cyclohexane pentanamide 
• 72155-54-5 2-oxazolidinone of 4(S)-amino-3(S)-hydroxy-5-phenylpentanoic acid 
• 72155-66-9 N-(tert-butoxycarbonyl)-4(S)-amino-3(S)-hydroxy-5-phenylpentanoyl-L-alanyl isoamylamide 
• 120742-12-3 N-Isovaleryl-L-valyl-L-valyl-4(S)-amino-3(S)-hydroxy-5-phenylpentanoic Acid Methyl Ester 
• 172912-08-2 cis-2-(tert-butyldiphenylsilyloxymethyl)-5-4-(Boc-AHPPA-1-oxo-6-aminopentyl)cytosin-1'-yl>-1,3-oxathiolane 
• 172912-03-7 BocAHPPA-Phe-Leu-Phe-OCH₃ 
• 172912-04-8 BocAHPPA-Phe-Leu-Phe 

Relevant articles and documents

AHPPA derivative and its preparation method

The invention discloses AHPPA derivatives and a preparation method thereof. The preparation method utilizes a diethylzinc-stannic chloride mixture with a mole ratio of 1: 2-4 as a catalyst, improves a reaction temperature and a yield and is suitable for industrial production.

Novel renin inhibitors containing derivatives of N-alkylleucyl-β-hydroxy-γ-amino acids

In search for new drugs lowering arterial blood pressure, which could be applied in anti-hypertensive therapy, research concerning agents blocking of renin-angiotensin-aldosteron system has been conducted. Despite many years of research conducted at many research centers around the world, aliskiren is the only one renin inhibitor, which is used up to now. Four novel potential renin inhibitors, having structure based on the peptide fragment 8-13 of human angiotensinogen, a natural substrate for renin, were designed and synthesized. All these inhibitors contain unnatural moieties that are derivatives of N-methylleucyl-β-hydroxy-γ-amino acids at the P2-P1' position: 4-[N-(N-methylleucyl)-amino]-3-hydroxy-7-(3-nitroguanidino)-heptanoic acid (AHGHA), 4-[N-(N-methylleucyl)-amino]-3-hydroxy-5-phenyl-pentanoic acid (AHPPA) or 4-[N-(N-methylleucyl)-amino]-8-benzyloxycarbonylamino-3-hydroxyoctanoic acid (AAHOA). The previously listed synthetic β-hydroxy-γ-amino acids constitute pseudodipeptidic units that correspond to the P1-P1' position of the inhibitor molecule. An unnatural amino acid, 4-methoxyphenylalanin (Phe(4-OMe)), was introduced at the P3 position of the obtained compounds. Three of these compounds contain isoamylamide of 6-aminohexanoic acid (ε-Ahx-Iaa) at the P2'-P3' position. The proposed modifications of the selected human angiotensinogen fragment are intended to increase bioactivity, bioavailability, and stability of the inhibitor molecule in body fluids and tissues. The inhibitor Boc-Phe(4-OMe)-MeLeu-AHGHA-OEt was obtained in the form of an ethyl ester. The hydrophobicity coefficient, expressed as log P varied between 3.95 and 8.17. In vitro renin inhibitory activity of all obtained compounds was contained within the range 10-6-10-9 M. The compound Boc-Phe(4-OMe)-MeLeu-AHPPA-Ahx-Iaa proved to be the most active (IC50 = 1.05 × 10-9 M). The compounds Boc-Phe(4-OMe)-MeLeu-AHGHA-Ahx-Iaa and Boc-Phe(4-OMe)-MeLeu-AHPPA-Ahx-Iaa are resistant to chymotrypsin.

Stereoselective synthesis of four possible isomers of streptopyrrolidine

The synthesis of (4R,5R)-streptopyrrolidine (1), (4S,5R)-streptopyrrolidine (2) (4R, 5S)-streptopyrrolidine (3) and (4S,5S)-strepto- pyrrolidine (4) have been achieved in a concise and highly efficient manner via a highly stereoselective aldol type reacti