174282-97-4

Basic information

• Product Name: Butanoic acid, 3-[[(1,1-dimethylethoxy)carbonyl]amino]-2-hydroxy-, (2R,3S)-
• Synonyms: Butanoic acid, 3-[[(1,1-dimethylethoxy)carbonyl]amino]-2-hydroxy-, (2R,3S)-;(2R,3S)-3-(tert-butoxycarbonylamino)-2-hydroxybutanoic acid
• CAS NO: 174282-97-4
• Molecular Formula: C9H17NO5
• Molecular Weight: 219.23498
• Product Categories: N-BOC
• Mol File: 174282-97-4.mol
• Article Data: 2

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Butanoic acid, 3-[[(1,1-dimethylethoxy)carbonyl]amino]-2-hydroxy-, (2R,3S)-(CAS DataBase Reference)
• NIST Chemistry Reference: Butanoic acid, 3-[[(1,1-dimethylethoxy)carbonyl]amino]-2-hydroxy-, (2R,3S)-(174282-97-4)
• EPA Substance Registry System: Butanoic acid, 3-[[(1,1-dimethylethoxy)carbonyl]amino]-2-hydroxy-, (2R,3S)-(174282-97-4)

Safety Data

• Hazardous Substances Data: 174282-97-4(Hazardous Substances Data)

Upstream product

• 174282-98-5 (2R,3S)-3-tert-Butoxycarbonylamino-2-hydroxy-butyric acid methyl ester 
• 174282-96-3 (2R,3S)-1-tert-butyldimethylsilyloxy-3-tert-butoxycarbonylamino-2-butanol 
• 174282-91-8 (2R,3S)-1-tert-butyldimethylsilyloxy-3-tert-butoxycarbonylamino-2-p-nitrophenylcarbonyloxybutane 
• 165683-82-9 (2S,3S)-1-(tert-butyldimethylsilyloxy)-3-(tert-butoxycarbonylamino)-2-butanol 
• 154079-54-6 (2S,3S)-3-tert-butoxycarbonylamino-1,2-butanediol 
• 24424-99-5 di-tert-butyl dicarbonate 

Relevant articles and documents

Synthesis and CD spectra of fluoro- and hydroxy-substituted β-peptides

β-Amino acids 1-3 with OH and F substituents in the α-position have been prepared (Scheme) from the natural (S)-α-amino acids alanine, valine, and leucine, and incorporated into β-hexa- and β-heptapeptides 4-12. The peptide syntheses were performed according to a conventional solution strategy (Boc/Bn protection) with fragment coupling. The new β-peptides with (series a) and without (series b) terminal protection were isolated in HPLC-pure form and characterized by NMR spectroscopy and MALDI mass spectrometry. The chemical properties as well as the patterns of the CD spectra (Figs. 3-5) depend upon constitution (OH, F, F2 substitution) and configuration (l or u) of the amino acid residues, upon the total number of OH and F substituents in the peptide chain, and upon the solvent used (H2O, MeOH, CF3CH2OH, (CF3)2CHOH). No reliable clues regarding the structures can be obtained from these CD spectra. Only a full NMR analysis will be able to answer the questions: a) with which known secondary structures (Figs. 1 and 2) of β-peptides are the OH and F derivatives compatible? b) Are new secondary structures enforced by the polar and/or H-bonding backbone substituents? Furthermore, the β-peptides described here will enable us to study changes in chemical, enzymatic, and metabolic stability, and in physiological properties caused by the heteroatoms.