288159-40-0

Basic information

• Product Name: N-BOC-(R)-2-AMINO-3-HYDROXY-3-METHYLBUTANOIC ACID
• Synonyms: BOC-(R)-2-AMINO-3-HYDROXY-3-METHYLBUTANOIC ACID;N-BOC-(R)-2-AMINO-3-HYDROXY-3-METHYLBUTANOIC ACID;Boc-(R)-2-amino-3-methylbutanoic acid;(R)-Boc-beta, beta-dimethyl-serine;N-Boc-3-hydroxy-D-valine, 97%;(R)-Boc-2-aMino-3-hydroxy-3-Methyl-butyric acid;(R)-Boc-beta-hydroxy-valine;3-Hydroxy-D-valine, N-BOC protected
• CAS NO: 288159-40-0
• Molecular Formula: C₁₀H₁₉NO₅
• Molecular Weight: 233.26
• Product Categories: unnatural amino acids
• Mol File: 288159-40-0.mol

Chemical Properties

• Boiling Point: 391.1±37.0 °C(Predicted)
• Appearance: /
• Density: 1.175±0.06 g/cm3(Predicted)
• Storage Temp.: 2-8°C
• PKA: 3.62±0.10(Predicted)
• CAS DataBase Reference: N-BOC-(R)-2-AMINO-3-HYDROXY-3-METHYLBUTANOIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: N-BOC-(R)-2-AMINO-3-HYDROXY-3-METHYLBUTANOIC ACID(288159-40-0)
• EPA Substance Registry System: N-BOC-(R)-2-AMINO-3-HYDROXY-3-METHYLBUTANOIC ACID(288159-40-0)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 288159-40-0(Hazardous Substances Data)

Usage

Chemical Properties

White powder

Upstream product

• 182958-73-2 (2R)-2-(N-tert-Butoxycarbonyl)amino-3-hydroxy-3-methylbutanoic acid 
• 95715-85-8 2-(tert-butoxycarbonylamino)-3-hydroxypropionic acid methyl ester 
• 24424-99-5 di-tert-butyl dicarbonate 

Downstream Products

• 884880-39-1 Fmoc-D-OHVal 
• 1428850-20-7 C₃₂H₄₈N₂O₅Si 

Relevant articles and documents

NIPECOTIC ACID DERIVATIVE AND USE THEREOF FOR MEDICAL PURPOSES

The present invention aims to provide a compound having an sEH-inhibiting activity and to provide a pharmaceutical having a therapeutic effect and a prophylactic effect on chronic renal disease and pulmonary hypertension based on the sEH-inhibiting action. The present invention provides nipecotic acid derivatives represented by the chemical formula below and pharmaceutically acceptable salts thereof.

Total synthesis of the large non-ribosomal peptide polytheonamide B

Polytheonamide B is by far the largest non-ribosomal peptide known at present, and displays extraordinary cytotoxicity (EC50 =68 pg ml -1 , mouse leukaemia P388 cells). Its 48 amino-acid residues include a variety of non-proteinogenic d- and l-amino acids, and the absolute stereochemistry of these amino acids alternate in sequence. These structural features induce the formation of a stable β-strand-type structure, giving rise to an overall tubular structure over 30A? in length. In a biological setting, this fold is believed to transport cations across the lipid bilayer through a pore, thereby acting as an ion channel. Here, we report the first chemical construction of polytheonamide B. Our synthesis relies on the combination of four key stages: syntheses of non-proteinogenic amino acids, a solid-phase assembly of four fragments of polytheonamide B, silver-mediated connection of the fragments and, finally, global deprotection. The synthetic material now available will allow studies of the relationships between its conformational properties, channel functions and cytotoxicity.

Serine as chiral educt for the practical synthesis of enantiopure N-protected β-hydroxyvaline

N-tert-Butyloxycarbonyl- and N-benzenesulfonyl-β-hydroxyvalines 1a and 1b were, respectively, synthesized in enantiomerically pure form by a two-step protocol from their enantiomeric N-protected serine methyl esters 2a and 2b. The addition of CH3MgBr to 2a and 2b provided diols 3a and 3b, respectively as major products in 83% and 81% yields. Selective oxidation of diols 3a and 3b was performed using a TEMPO, NaClO2, NaOCl cocktail in 96% and 93% respective yields. This two-step process effectively furnished multigram amounts of enantiopure N-Boc-β-hydroxyvaline 1a.