153287-86-6

Basic information

• Product Name: BOC-L-ASPARTIMOL T-BUTYL ESTER
• Synonyms: BOC-L-ASPARTIMOL T-BUTYL ESTER;Boc-L-aspartinol 4-tert-Butyl Ester;(S)-t-Butyl 3-(t-butoxycarbonylaMino)-4-hydroxy butanoate;tert-Butyl (S)-3-(Boc-amino)-4-hydroxybutanoate;tert-butyl(S)-3-((tert-butoxycarbonyl)amino)-4-hydroxybutanoate;tert-butyl (3S)-3-[(tert-butoxycarbonyl)amino]-4-hydroxybutanoate;EOS-61497
• CAS NO: 153287-86-6
• Molecular Formula: C₁₃H₂₅NO₅
• Molecular Weight: 275.34
• Product Categories: pharmacetical
• Mol File: 153287-86-6.mol
• Article Data: 29

Chemical Properties

• Boiling Point: 393.4°Cat760mmHg
• Flash Point: 191.7°C
• Appearance: /
• Density: 1.071g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.464
• Storage Temp.: 2-8°C
• PKA: 11.54±0.46(Predicted)
• CAS DataBase Reference: BOC-L-ASPARTIMOL T-BUTYL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: BOC-L-ASPARTIMOL T-BUTYL ESTER(153287-86-6)
• EPA Substance Registry System: BOC-L-ASPARTIMOL T-BUTYL ESTER(153287-86-6)

Safety Data

• Hazardous Substances Data: 153287-86-6(Hazardous Substances Data)

Usage

General Description

BOC-L-ASPARTIMOL T-BUTYL ESTER is a chemical compound with the molecular formula C15H25NO5. It is a t-butyl ester derivative of L-aspartimide and is commonly used as a building block in organic synthesis. Its primary application lies in the preparation of peptide-based drugs and pharmaceuticals. As a protected form of aspartic acid, BOC-L-ASPARTIMOL T-BUTYL ESTER is also utilized in the synthesis of peptides and peptidomimetics, where it serves to protect the reactive functional groups and facilitate chemical reactions. It is considered a valuable intermediate in the field of medicinal chemistry and organic synthesis.

InChI:InChI=1/C13H25NO5/c1-12(2,3)18-10(16)7-9(8-15)14-11(17)19-13(4,5)6/h9,15H,7-8H2,1-6H3,(H,14,17)/t9-/m0/s1

Upstream product

• 18635-49-9 4-tert-butyl 1-methyl L-N-(tert-butoxycarbonyl)aspartate 
• 50715-50-9 O¹-(2,5-dioxopyrrolidin-1-yl)-O⁴-tert-butyl-(2S)-2-(tert-butoxycarbonylamino)-butanedioate 
• 1676-90-0 Boc-Asp(OtBu)-OH 
• 543-27-1 isobutyl chloroformate 
• 1913-12-8 β-tert-butyl-N-(tert-butoxycarbonyl)-L-aspartic acid dicyclohexylammonium salt 
• 3057-74-7 L-Asp(t-Bu) 
• 24424-99-5 di-tert-butyl dicarbonate 

Downstream Products

• 220542-06-3 tert-butyl 3(S)-(tert-butoxycarbonylamino)-4-(p-tolylsulfonyloxy)butanoate 
• 911635-43-3 3-t-butoxycarbonylamino-4-(5,5-difluoro-2-oxo-piperidin-1-yl)butyric acid 
• 1393721-13-5 (S)-tert-butyl 4-(benzyl(methyl)amino)-3-(tert-butoxycarbonylamino)butanoate 
• 1802736-56-6 (3S)-3-[(tert-butoxycarbonyl)amino]-4-iodobutanoic acid tert-butyl ester 
• 1246261-58-4 Z-Val-Asp(β-tert-butyl)vinyl methylsulfone 

Relevant articles and documents

Synthesis and evaluation of L-cystathionine as a standard for amino acid analysis

L-Cystathionine is a key nonprotein amino acid related to metabolic conditions. The quantitative determination of L-cystathionine in physiological fluids by amino acid analysis is important for clinical diagnosis; however, certified reference material for L-cystathionine with satisfactory purity, content, and quantity has been unavailable until recently. Consequently, a practical and simple method for the preparation of L-cystathionine was examined, which involves thioalkylation of N-tert-butoxycarbonyl-Lcysteine tert-butyl ester, derived from L-cystine, with (2S)-2-(tert-butoxycarbonyl)amino-4-iodobutanoic acid tert-butyl ester, derived from L-aspartic acid, to obtain L-cystathionine with protecting groups, followed by single-step deprotection under mild conditions. This method produces L-cystathionine in high purity (99.4%) and having sufficient percentage content according to amino acid analysis, which could be used as a standard for the amino acid analysis of physiological fluids.

Methyl effect in azumamides provides insight into histone deacetylase inhibition by macrocycles

Natural, nonribosomal cyclotetrapeptides have traditionally been a rich source of inspiration for design of potent histone deacetylase (HDAC) inhibitors. We recently disclosed the total synthesis and full HDAC profiling of the naturally occurring azumamides (J. Med. Chem. 2013, 56, 6512). In this work, we investigate the structural requirements for potent HDAC inhibition by macrocyclic peptides using the azumamides along with a series of unnatural analogues obtained through chemical synthesis. By solving solution NMR structures of selected macrocycles and combining these findings with molecular modeling, we pinpoint crucial enzyme-ligand interactions required for potent inhibition of HDAC3. Docking of additional natural products confirmed these features to be generally important. Combined with the structural conservation across HDACs 1-3, this suggests that while cyclotetrapeptides have provided potent and class-selective HDAC inhibitors, it will be challenging to distinguish between the three major class I deacetylases using these chemotypes.

PYRAZOLE DERIVATIVE, OR PHARMACEUTICALLY ACCEPTABLE SALT THEREOF

[Problem] The present invention is to provide a novel pyrazole derivative, or a pharmaceutically acceptable salt thereof, a pharmaceutical composition comprising the same, and a pharmaceutical use thereof. [Solution] The present invention provides a compound represented by the formula (I) or a pharmaceutically acceptable salt thereof, which has TRPM8 inhibitory effects: wherein ring A is C6-10 aryl or the like; X is CR4a or the like; R1 and R2 are a hydrogen atom or the like; R3 is a hydrogen atom or the like; R4 is a hydrogen atom or the like; ring B is C6-10 aryl or the like; R5 is a hydrogen atom or the like; R6a is a hydrogen atom or the like; R7a is a hydrogen atom or the like; R7b is a hydrogen atom or the like; R6b is a hydrogen atom or the like; R8 is a hydrogen atom or the like; n is 0, 1 or 2. Therefore, the compound represented by the formula (I) of the present invention or a pharmaceutically acceptable salt thereof is useful as an agent for treating or preventing diseases or symptoms caused by hyperexcitability or disorder of afferent neurons.

BETA-SUBSTITUTED BETA-AMINO ACIDS AND ANALOGS AS CHEMOTHERAPEUTIC AGENTS AND USES THEREOF

β-Substituted β-amino acids, β-substituted β-amino acid derivatives, and β-substituted β-amino acid analogs and (bio)isosteres and their use as chemotherapeutic agents are disclosed. The β-substituted β-amino acid derivatives and β-substituted β-amino acid analogs and (bio)isosteres are selective LAT1/4F2hc substrates and exhibit rapid uptake and retention in tumors expressing the LAT1/4F2hc transporter. Methods of synthesizing the β-substituted β-amino acid derivatives and β-substituted β-amino acid analogs and methods of using the compounds for treating cancer are also disclosed. The β-substituted β-amino acid derivatives and β-substituted β-amino acid analogs exhibit selective uptake in tumor cells expressing the LAT1/4F2hc transporter and accumulate in cancerous cells when administered to a subject in vivo. The β-substituted β-amino acid derivatives and β-substituted β-amino acid analogs and (bio)isosteres exhibit cytotoxicity toward several tumor types.