313672-19-4

Usage

General Description

" (R)-(-)-N(alpha)-Benzyl-N(beta)-Boc-(D)-Hydrazinovaline is a chemical compound with the molecular formula C18H28N4O4. It is a derivative of L-valine and is commonly used as a building block in the synthesis of peptide and protein-based drugs. The compound is a chiral molecule and exists in two enantiomeric forms, with the (R)-(-)-enantiomer being the active form. It is often used in the pharmaceutical industry for the development of drugs targeting diseases such as cancer and diabetes. The compound has potential therapeutic applications due to its ability to target specific biological processes related to disease pathways. Additionally, the compound's structural features make it useful for creating novel peptide-based drugs with improved pharmacokinetic and pharmacodynamic properties."

InChI:InChI=1/C17H26N2O4/c1-12(2)14(15(20)21)19(11-13-9-7-6-8-10-13)18-16(22)23-17(3,4)5/h6-10,12,14H,11H2,1-5H3,(H,18,22)(H,20,21)/p-1/t14-/m1/s1

Upstream product

• 15363-84-5 (S)-2-(benzylamino)-3-methylbutanoic acid 
• 150884-56-3 N-tert-butyloxycarbonyl-3-(4-cyanophenyl)oxaziridine 
• 219547-77-0 t-butyl 3-(trichloromethyl)-1,2-oxaziridine-2-carboxylate 
• 98575-68-9 (R)-N-benzylvaline 
• 150884-51-8 1,1-dimethylethyl N-[(4-cyanophenyl)methylen]carbamate 
• 68014-21-1 triphenyl(t-butoxycarbonylimino)phosphorane 
• 1070-19-5 N-(tert-butyloxycarbonyl) azide 
• 100-52-7 benzaldehyde 
• 72-18-4 L-valine 

Relevant academic research and scientific papers

Discovery of a new class of macrocyclic antagonists to the human motilin receptor

A novel class of macrocyclic peptidomimetics was identified and optimized as potent antagonists to the human motilin receptor (hMOT-R). Well-defined structure-activity relationships allowed for rapid optimization of potency that eventually led to high aff

Electrophilic Amination of Amino Acids with N-Boc-oxaziridines: Efficient Preparation of N-Orthogonally Diprotected Hydrazino Acids and Piperazic Acid Derivatives

A general two-step preparation of enantiopure Nα,N β-orthogonally diprotected α-hydrazino acids 1 is developed on a multigram scale. The key reaction is the efficient electrophilic amination of N-benzyl amino acids 6 with N-Boc-oxaziridine 7 and accommodates various functional groups encountered in side chains of amino acids. The cyclic 2,3,4,5-tetrahydro-3-pyridazine carboxylic acid (piperazic acid) derivatives 2 and 3 or the cyclic 3,4-dihydro-3-pyrazolecarboxylate 4 are conveniently prepared from glutamic acid or aspartic acid via orthogonally diprotected α-hydrazino acids 1m and 1n.

Synthesis, CD Spectra, and Enzymatic Stability β 2-Oligoazapeptides Prepared from (S)-2-Hydrazino Carboxylic Acids Carrying the Side Chains of Val, Ala, and Leu

β-Peptides offer the unique possibility to incorporate additional heteroatoms into the peptidic backbone (Figs. 1 and 2). We report here the synthesis and spectroscopic investigations of β2-peptide analogs consisting of (S)-3-aza-β-amino acids

N-alkyloxycarbonyl-3-aryloxaziridines: Their preparation, structure, and utilization as electrophilic amination reagents

This paper reports the synthesis of a series of N-protected oxaziridines (N-Moc, Boc, Z or Fmoc) and discusses their ability to deliver their N-alkoxycarbonyl fragment to amines, enolates, sulfur, and phosphorus nucleophiles (electrophilic amination). These oxaziridines are prepared by oxidation of the corresponding imines with oxone or anhydrous MCPBA lithium salt as the source of oxygen. They transfer their N-protected fragment to primary and secondary amines to give protected hydrazines in fair to excelent yield. The nitrogen transfer to free amino acids (in form of their R4N+ salts) is particularly fast, even at low temperature, providing L (or D) N-protected α-hydrazino acids. Enolates are C-aminated to give N-protected α-amino ketones, esters, or amides in modest yield, due to a side aldol reaction of the unreacted enolate with the released benzaldehyde. With tertiary amines (Et3N), sulfides (PhSMe), and phosphines (Ph3P), amination and oxidation proceed in a parallel way; the amount of amination product increases when the temperature is lowered (kinetic control). Some of the factors that can orient the oxaziridine reactivity towards amination or oxidation of nucleophiles are considered.