58521-49-6

Basic information

• Product Name: BOC-STA-OH
• Synonyms: (3S,4S)-3-Hydroxy-4-(tert-butyloxycarbonylamino)-6-methylheptanoic acid;(3S,4S)-3-Hydroxy-4-[(tert-butyloxycarbonyl)amino]-6-methylheptanoic acid;(3S,4S)-3-Hydroxy-4-[(tert-butyloxycarbonyl)amino]6-methylheptanoic acid;(3S,4S)-4-(tert-Butoxycarbonylamino)-3-hydroxy-6-methylheptanoic acid;(3S,4S)-Boc-Statine;(3S,4S)-4-[(tert-Butylcarbonyl)amino]-3-hydroxy-6-methylheptanoic acid;BOC-Statine [Boc-Sta(3S,4S)-OH];N-tert-Butoxycarbonyl-(3S,4S)-statine
• CAS NO: 58521-49-6
• Molecular Formula: C₁₃H₂₅NO₅
• Molecular Weight: 275.34
• Product Categories: inhibitor;Amino Acids
• Mol File: 58521-49-6.mol
• Article Data: 28

Chemical Properties

• Melting Point: 119-122 °C
• Boiling Point: 439.98°C at 760 mmHg
• Flash Point: 219.892°C
• Appearance: /
• Density: 1.107g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.479
• Storage Temp.: 2-8°C
• CAS DataBase Reference: BOC-STA-OH(CAS DataBase Reference)
• NIST Chemistry Reference: BOC-STA-OH(58521-49-6)
• EPA Substance Registry System: BOC-STA-OH(58521-49-6)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• F: 10
• HazardClass: IRRITANT
• Hazardous Substances Data: 58521-49-6(Hazardous Substances Data)

Usage

Chemical Properties

Amorphous white powder

InChI:InChI=1/C13H25NO5/c1-8(2)6-9(10(15)7-11(16)17)14-12(18)19-13(3,4)5/h8-10,15H,6-7H2,1-5H3,(H,14,18)(H,16,17)/t9-,10+/m1/s1

Upstream product

• 112700-38-6 (5S)-4-hydroxy-5-isobutyl-1-t-butoxycarbonylpyrrol-2(5H)-one 
• 158257-39-7 Z-(4S,5S)-4-hydroxy-pyrrolidin-2-one 
• 158257-37-5 (S)-3-Hydroxy-2-isobutyl-5-oxo-2,5-dihydro-pyrrole-1-carboxylic acid benzyl ester 
• 66866-66-8 phenylmethyl (4S)-4-(2-methylpropyl)-5-oxo-1,3-oxazolidine-3-carboxylate 
• 127000-63-9 (4S,5S)-5-isobutyl-4-hydroxy-2-oxopyrrolidine 
• 537035-59-9 (2R,3S,R_S)-N-(tert-butoxycarbonyl)-3-amino-5-methyl-1-[(4-methylphenyl)sulfinyl]-2-hexanol 
• 472999-82-9 (3S,R_S)-N-(tert-butoxycarbonyl)-3-amino-5-methyl-1-[(4-methylphenyl)sulfinyl]-2-hexanone 
• 537035-61-3 (2R,3S)-N-(tert-butoxycarbonyl)-3-amino-5-methyl-1-[(4-methylphenyl)sulfenyl]-2-hexanol 
• 537035-64-6 (4S,5S)-3-(tert-butoxycarbonyl)-5-cyanomethyl-4-isobutyl-2,2-dimethyl-1,3-oxazolidine 
• 174145-77-8 (3S,4S)-4-[(tert-butoxycarbonyl)amino]-3-hydroxy-6-methylheptanonitrile 
• 219702-17-7 (4S,5S)-4-Isobutyl-2,2-dimethyl-5-(2-oxo-ethyl)-oxazolidine-3-carboxylic acid tert-butyl ester 
• 107202-51-7 (2R)-2-[(1S)-1-[N-(tert-butyloxycarbonyl)amino]-3-methylbutyl]oxirane 
• 58521-45-2 tert-butoxycarbonyl-L-leucinal 
• 254752-24-4 (S)-4-(tert-butoxycarbonylamino)-6-methyl-1-trimethylsilylhept-1-yn-3-one 

Downstream Products

• 49642-07-1 statine 
• 918797-30-5 6-tert-butoxycarbonylamino-2-{2-[4-(4-{1-[1-(2-butylcarbamoyl-1-hydroxy-ethyl)-3-methyl-butylcarbamoyl]-2-methyl-butylcarbamoyl}-phenoxy)-benzoylamino]-4-methyl-pentanoylamino}-hexanoic acid propyl ester 

Relevant articles and documents

Asymmetric synthesis via acetal templates. 14. Preparation of enatiomerically pure (3S,4S)- and (3S,4R)-statine derivatives

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New potential renin inhibitors with dipeptide replacements in the molecule

A series of eight non-peptidic potential renin inhibitors have been designed and synthesized. All of them contain dipeptide replacement: (3S,4S)-4-amino-5-cyclohexyl-3-hydroxypentanoic acid (ACHPA) in their molecules. Four among them comprise two additional analogs of dipeptide: (3S,4S)-4-amino-3-hydroxy-5-phenylpentanoic acid (AHPPA) and (3S,4S)-4-amino-3-hydroxy-6-methylheptanoic acid (statine, Sta). All of the synthesized compounds contain also hydrophobic portions to receive a moderate lipophilicity of the molecules. Inhibitory activity of the compounds was measured in vitro by HPLC determination of Leu-Val-Tyr-Ser released from the N-acetyltetradecapeptide substrate by renin in the presence of the inhibitor. Asp-α(OEt)-(S,S)-ACHPA-εAhx-Iaa (23) shows inhibitory activity (7%) at the concentration of 1.0 × 10-2 M. The other synthesized compounds show no inhibitory activity up to this concentration.

High antiplasmodial activity of novel plasmepsins I and II inhibitors

The aim of this study was to develop new antiplasmodial compounds acting through distinct mechanisms during both the liver and the blood stages of the parasite life cycle. Compounds were designed on the basis of the "double-drug" approach: primaquine, whi