87694-52-8

Basic information

• Product Name: BOC-L-LEUCINE N,O-DIMETHYLHYDROXAMIDE
• Synonyms: BOC-VAL-NME(OME);BOC-VAL-N(OCH3)CH3;BOC-L-VALINE N-METHOXY-N-METHYL AMIDE;BOC-L-VALINE N,O-DIMETHYLHYDROXAMIDE;BOC-L-LEUCINE N,O-DIMETHYLHYDROXAMIDE;BOC-LEU-NME(OME);BOC-LEU-N(OME)ME;N-ALPHA-T-BOC-L-VALINE N-METHOXY-N-METHYL AMIDE
• CAS NO: 87694-52-8
• Molecular Formula: C₁₂H₂₄N₂O₄
• Molecular Weight: 260.33
• Product Categories: Amino Acids;Amino Acid Derivatives;Peptide Synthesis;Valine
• Mol File: 87694-52-8.mol

Chemical Properties

• Boiling Point: 235 °C(lit.)
• Flash Point: >230 °F
• Appearance: White to pale yellow/Low Melting Solid or Liquid
• Density: 1.46 g/mL at 25 °C(lit.)
• Refractive Index: n20/D 1.454(lit.)
• Storage Temp.: Store at 0-5°C
• PKA: 11.11±0.46(Predicted)
• CAS DataBase Reference: BOC-L-LEUCINE N,O-DIMETHYLHYDROXAMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: BOC-L-LEUCINE N,O-DIMETHYLHYDROXAMIDE(87694-52-8)
• EPA Substance Registry System: BOC-L-LEUCINE N,O-DIMETHYLHYDROXAMIDE(87694-52-8)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 87694-52-8(Hazardous Substances Data)

Usage

Chemical Properties

White to off-white crystalline powder

Uses

Reduced by LiAlH4 to give the corresponding Boc amino acid aldehyde.

Upstream product

• 13734-41-3 t-Boc-L-valine 
• 6638-79-5 N,O-dimethylhydroxylamine*hydrochloride 
• 1117-97-1 N,0-dimethylhydroxylamine 
• 54430-66-9 [(1S)-1-(imidazole-1-carbonyl)-2-methylpropyl]-carbamic acid tert-butyl ester 
• 24424-99-5 di-tert-butyl dicarbonate 
• 72-18-4 L-valine 
• 133010-02-3 1,1-dimethylethyl S-N-(1-fluorocarbonyl-2-methylpropyl)carbamate 

Downstream Products

• 145037-78-1 (3S)-3-(tert-butyloxycarbonylamino)-4-methyl-1-phenylpentan-2-one 
• 79069-51-5 (S)-N-tert-butoxycarbonylvalinal 
• 295800-05-4 (S)-tert-butyl (3-methyl-1-oxo-1-phenylbutan-2-yl)carbamate 
• 1025959-11-8 [1-(4-fluoro-benzoyl)-2-methyl-propyl]-carbamic acid tert-butyl ester 
• 143327-78-0 tert-butyl [(1S)-1-isopropylprop-2-yn-1-yl]carbamate 
• 871210-22-9 (4S,5R)-4-iso-propyl-5-(1'H,1'H,2'H,2'H-perfluorooctyl)-2-oxazolidinone 
• 866104-96-3 C₂₉H₃₁N₂OP 
• 774600-84-9 tert-butyl (Z)-N-{(2S)-1-[(diphenylphosphinoyl)imino]-3-methyl-1-phenyl-2-butyl}carbamate 
• 866104-97-4 C₂₉H₃₀FN₂OP 
• 774600-85-0 tert-butyl (Z)-N-{(2S)-1-[(diphenylphosphinoyl)imino]-1-(4-fluorophenyl)-3-methyl-2-butyl}carbamate 

Relevant articles and documents

Design, Synthesis, and Biological Activity of Isosyringolin A

Isosyringolin A, which is an isomer of the proteasome-inhibiting natural product syringolin A, was designed and synthesized to develop analogues that are step economical and synthetically accessible in a practical manner. It was revealed that isosyringolin A exhibited proteasome-inhibitory activity comparable to that of syringolin A and that its derivatization leads to great enhancement in its proteasome inhibitory activity as well as its cytotoxicity against human myeloma cells.

Convenient Synthesis of Alternatively Bridged Tryptophan Ketopiperazines and Their Activities against Trypanosomatid Parasites

There is an urgent need for the development of new treatments against trypanosomatid parasites; the causative agents of some of the most debilitating diseases in the developing world. This work targets an interesting 6-5-6-6 fused carboline scaffold, accessing a range of substituted derivatives through stereospecific intramolecular Pictet–Spengler condensation. Modification of the cyclisation conditions allowed retention of the carbamate protecting group and gave insight into the reaction mechanism. Compounds’ bioactivities were measured against T. brucei, T. cruzi, L. major and HeLa cells. We have identified promising pan-trypanocidal lead compounds based on the core scaffold, and highlight key SAR trends which will be useful for the future development of these compounds as potent trypanocidal agents.

Diastereoselective Synthesis of Nonplanar 3-Amino-1,2,4-oxadiazine Scaffold: Structure Revision of Alchornedine

Herein, we report the diastereoselective synthesis of a 3-amino-1,2,4-oxadiazine (AOXD) scaffold. The presence of a N-O bond in the ring prevents the planar geometry of the aromatic system and induces a strong decrease in the basicity of the guanidine moiety. While DIBAL-H appeared to be the most efficient reducing agent because it exhibited high diastereoselectivity, we observed various behaviors of the Mitsunobu reaction on the resulting β-aminoalcohol, leading to either inversion or retention of the configuration depending on the steric hindrance in the vicinity of the hydroxy group. The physicochemical properties (pKa and log D) and hepatic stability of several AOXD derivatives were experimentally determined and found that the AOXD scaffold possesses promising properties for drug development. Moreover, we synthesized alchornedine, the only natural product with the AOXD scaffold. Based on a comparison of the analytical data, we found that the reported structure of alchornedine was incorrect and hypothesized a new one.

PYRROLIDINE DERIVATIVE

The present invention aims to provide a novel compound which has CGRP receptor antagonist activity and which is useful for the treatment of various diseases mediated by CGRP receptors. That is, the present invention relates to the pyrrolidine derivatives represented by the following formula (I) or a pharmaceutically acceptable salt thereof. In the formulae, W is ring, X is a carbon atom or the like, Y1 to Y4 are carbon atoms or the like, and R1 to R7 is alkyl or the like. The compounds of the present invention or a pharmaceutically acceptable salt thereof have an excellent CGRP receptor antagonist activity, and thus are useful as agents for the treatment of various diseases mediated by CGRP receptors.

Enzymatic Macrocyclization of 1,2,3-Triazole Peptide Mimetics

The macrocyclization of linear peptides is very often accompanied by significant improvements in their stability and biological activity. Many strategies are available for their chemical macrocyclization, however, enzyme-mediated methods remain of great interest in terms of synthetic utility. To date, known macrocyclization enzymes have been shown to be active on both peptide and protein substrates. Here we show that the macrocyclization enzyme of the cyanobactin family, PatGmac, is capable of macrocyclizing substrates with one, two, or three 1,4-substituted 1,2,3-triazole moieties. The introduction of non-peptidic scaffolds into macrocycles is highly desirable in tuning the activity and physical properties of peptidic macrocycles. We have isolated and fully characterized nine non-natural triazole-containing cyclic peptides, a further ten molecules are also synthesized. PatGmac has now been shown to be an effective and versatile tool for the ring closure by peptide bond formation.

Radiolabeled antagonistic bombesin peptidomimetics for tumor targeting

The replacement of amide bonds in the backbone of peptides by proteolytically stable 1,2,3-triazole isosteres can provide novel peptidomimetics with promising properties for the development of tumor-targeting radiopeptides. On the basis of our previous work with radiolabeled agonistic bombesin (BBN) derivatives of the sequence [Nle14]BBN(7-14), we substituted selected amide bonds of the structurally closely related antagonistic peptide analog JMV594. With the exception of the C-terminal modification, amide-to-triazole substitutions tolerated by [Nle 14]BBN(7-14) without loss of biological function led to abolished receptor affinity in the case of JMV594. These findings provide an additional piece of evidence for the currently disputed differences in the modes of action of agonistic and antagonistic gastrin-releasing peptide receptor (GRPR)-targeting radiopeptides.

Tosylhydrazide-promoted diastereoselective intramolecular 1,3-dipolar cycloadditions: Synthesis of tetrahydropyrrolo[3,4-c]pyrazoles

A very straightforward diastereoselective synthesis of tetrahydropyrrolo[3, 4-c]pyrazoles by intramolecular 1,3-dipolar cycloaddition is described. The starting materials for the synthetic route are N-Boc-protected α-amino acids, which are first transformed into N-allyl-α-amino ketones through conventional methodologies. Then, a one-pot sequence that involves formation of a tosylhydrazone from the ketone, base-induced decomposition of the hydrazone, and intramolecular 1,3-dipolar cycloaddition of the diazo compound generated, gives rise to the bicyclic systems with total diastereoselectivity and high preservation of the enantiomeric purity. However, the analogous process employing α-amino aldehydes lacks stereoselectivity. DFT computational modeling has been carried out to account for the different behavior of the two types of systems. Copyright

Tosylhydrazide-Promoted Diastereoselective Intramolecular 1,3-Dipolar Cycloadditions: Synthesis of Tetrahydropyrrolo[3,4-c]pyrazoles

A very straightforward diastereoselective synthesis of tetrahydropyrrolo[3,4-c]pyrazoles by intramolecular 1,3-dipolar cycloaddition is described. The starting materials for the synthetic route are N-Boc-protected α-amino acids, which are first transformed into N-allyl-α-amino ketones through conventional methodologies. Then, a one-pot sequence that involves formation of a tosylhydrazone from the ketone, base-induced decomposition of the hydrazone, and intramolecular 1,3-dipolar cycloaddition of the diazo compound generated, gives rise to the bicyclic systems with total diastereoselectivity and high preservation of the enantiomeric purity. However, the analogous process employing α-amino aldehydes lacks stereoselectivity. DFT computational modeling has been carried out to account for the different behavior of the two types of systems.

Synthesis of new simplified hemiasterlin derivatives with α,β-unsaturated carbonyl moiety

In this Letter, we report a convenient and efficient method for the synthesis of new simplified derivatives of hemiasterlin in which the α,α-dimethylbenzylic moiety A is replaced by α,β- unsaturated aryl groups as Michael acceptor. Most of these derivatives have a strong cytotoxic activity on three human tumor cell lines (KB, Hep-G2 and MCF7). Analogs 17b and 17f showed a high cytotoxicity against KB and Hep-G2 cancer cell lines comparable to paclitaxel and ellipticine.

1,2,3-Triazoles as amide bond mimics: Triazole scan yields protease-resistant peptidomimetics for tumor targeting

The triazole makes the difference: Replacement of amide bonds in the backbone of peptides by 1,4-disubstituted 1,2,3-triazole isosteres affords peptidomimetics with retained receptor affinity and cell-internalization properties, enhanced proteolytic stability, and improved tumor-targeting capabilities. Copyright