67919-80-6

Upstream product

• 186581-53-3 diazomethane 
• 109208-68-6 Boc-Ala-O-COO-isoBu 
• 15761-38-3 L-N-Boc-Ala 
• 631914-55-1 Boc-L-Ala-Cl 
• 24424-99-5 di-tert-butyl dicarbonate 
• 18107-18-1 diazomethyl-trimethyl-silane 
• 543-27-1 isobutyl chloroformate 
• 70-25-7 N-Methyl-N'-nitro-N-nitrosoguanidine 
• 60286-91-1 C₁₁H₁₉NO₅ 

Downstream Products

• 1321589-47-2 (S,S)-1-tert-butyl 3-methyl 2-methyl-4-oxo-6-propyl-3,4-dihydropyridine-1,3(2H)-dicarboxylate 
• 1321589-54-1 (2S,3S)-tert-butyl 3-acetoxy-2-methyl-4-oxo-6-propyl-3,4-dihydropyridine-1(2H)-carboxylate 
• 126027-07-4 tert-butyl N-[(1S)-1-methyl-2-oxo-propyl]carbamate 
• 93371-30-3 tert-butyl [(2S)-4-chloro-3-oxobutan-2-yl]carbamate 
• 106539-14-4 (S)-methyl 3-(tert-butyloxycarbonylamino)butyrate 
• 223922-53-0 [3-(benzyl-isopropyl-amino)-1-methyl-propyl]-carbamic acid tert-butyl ester 
• 118173-26-5 (S)-3-tert-butoxycarbonylamino-butanal 
• 245124-02-1 (2S,4S)-N-(tert-Butoxycarbonyl)-2-cyclohexyl-4-methyltetrahydro-2H-1,3-oxazine 

Relevant academic research and scientific papers

Reversible enolizafion of β-amino carboxamides by lithium hexamethyldisilazide

The enolization of β-amino carboxamides by lithium hexamethyldisilazide (LiHMDS) in THF/ toluene and subsequent diastereoselective alkylation with CH3I are reported. In situ IR spectroscopic studies reveal that β-amino carboxamides coordinate to LiHMDS at -78°C before enolization. Comparison with structurally similar carboxamides suggests that the β-amino group promotes the enolization. IR spectroscopic studies also show that the enolization is reversible. Efficient trapping of the enolate by CH3I affords full conversion to products. 6Li and 15N NMR spectroscopic studies reveal that lithium enolate-LiHMDS mixed dimers and trimers as well as a homoaggregated enolate are formed during the reaction. At ambient temperature, racemization of the β-position through a putative reversible Michael addition was observed.

Modulation of the Passive Permeability of Semipeptidic Macrocycles: N- And C-Methylations Fine-Tune Conformation and Properties

Incorporating small modifications to peptidic macrocycles can have a major influence on their properties. For instance, N-methylation has been shown to impact permeability. A better understanding of the relationship between permeability and structure is of key importance as peptidic drugs are often associated with unfavorable pharmacokinetic profiles. Starting from a semipeptidic macrocycle backbone composed of a tripeptide tethered head-to-tail with an alkyl linker, we investigated two small changes: peptide-to-peptoid substitution and various methyl placements on the nonpeptidic linker. Implementing these changes in parallel, we created a collection of 36 compounds. Their permeability was then assessed in parallel artificial membrane permeability assay (PAMPA) and Caco-2 assays. Our results show a systematic improvement in permeability associated with one peptoid position in the cycle, while the influence of methyl substitution varies on a case-by-case basis. Using a combination of molecular dynamics simulations and NMR measurements, we offer hypotheses to explain such behavior.

Rhodium catalyzed C-C bond cleavage/coupling of 2-(azetidin-3-ylidene)acetates and analogs

The C-C bond cleavage/coupling of 2-(azetidin-3-ylidene)acetates with aryl boronic acids catalyzed by a rhodium complex was studied with a "conjugate addition/β-C cleavage/protonation" strategy.

Photoinduced Multicomponent Synthesis of α-Silyloxy Acrylamides, an Unexplored Class of Silyl Enol Ethers

The photoinduced, multicomponent reaction of α-diazoketones, silanols, and isocyanides affords α-silyloxy acrylamides, formally derived from α-keto amides. The presence of a secondary amido group makes classic preparative methods for silyl enol ethers unfeasible in this case, while the mild conditions required by this photochemical approach allow their synthesis in good yields; moreover, the general structure can be easily modified by varying each component of the multicomponent reaction. Fine-tuning of the reaction conditions (i.e., solvents, radiation, additives) can be exploited to obtain complete Z selectivity. The reactivity of this overlooked class of silyl enol ethers has been investigated, and features that could pave the way to new applications have been found.

Amine compound for inhibiting SSAO/VAP-1 and application thereof in medicines

The present invention relates to an amine compound for inhibiting SSAO/VAP-1 and application thereof in medicines. In particular, the present invention relates to an amine compound for inhibiting a semicarbazide-sensitive oxidase (SSAO) and/or vascular adhesion protein-1 (VAP-1) inhibitor, or a pharmaceutically acceptable salt thereof, a stereoisomer or an/a E/Z isomer, further relates to a pharmaceutical composition containing the amine compound. The invention further relates to the application of the amine compound and the pharmaceutical composition in manufacture of the medicines for treatment of inflammation, inflammation-related diseases and immune diseases.

Synthesis of enantiopure dehydropiperidinones from α-amino acids and alkynes via azetidin-3-ones

Chiral dehydropiperidinones were synthesized in enantiopure form from α-amino acids and alkynes via azetidin-3-ones.

Synthesis of N-urethane protected α-aminoalkyl-α-cyanomethyl ketones; Application to the synthesis of 3-substituted 5-amino-1H-pyrazole tethered peptidomimetics

The preparation of N-protected amino/peptide α-cyanomethyl ketones through cyanation of the corresponding α-bromomethyl ketones is described. The utility of the resulting α-cyanomethyl ketones in the synthesis of 3-substituted-5-amino-1H-pyrazoles has also been demonstrated. In both steps a wide range of N-protected amino/peptide acids has been employed and the products are obtained in good yield. The enantiomeric purity of both the α-cyanomethyl ketones and pyrazoles were confirmed by chiral HPLC analysis of the corresponding Z-protected d- and l-Ala-OH as model substrates. The synthesis of peptide pyrazolecarboxamides is also delineated. Georg Thieme Verlag Stuttgart · New York.

CuI-promoted one-pot synthesis of N-boc protected β-ketotriazole amino acids: Application in the synthesis of new class of dipeptidomimetics

One-pot click chemistry of Nα-Boc-bromomethylketones, NaN3 and propiolic acid affords N-Boc protected 1,4- disubstituted 1,2,3-β-ketotriazole acids in good to excellent yield. The use of CuI as catalyst and DMSO as solvent leads the click react

TAPP analogs containing β3-homo-amino acids: Synthesis and receptor binding

β-Amino acids containing α,β-hybrid peptides show great potential as peptidomimetics. In this paper, we describe the synthesis and affinity to μ-opioid and δ-opioid receptors of α,β-hybrids, analogs of the tetrapeptide Tyr- d-Ala-Phe-Phe-NH2 (TAPP). Each amino acid was replaced with an l- or d-β3-h-amino acid. All α,β-hybrids of TAPP analogs were synthesized in solution and tested for affinity to μ-opioid and δ-opioid receptors. The analog Tyr-β3h- d-Ala-Phe-PheNH2 was found to be as active as the native tetrapeptide.

Enantiospecific synthesis of pyridinones as versatile intermediates toward asymmetric piperidines

The enantiospecific syntheses of pyridinones from amino acids via a gold-catalyzed strategy are reported. Excellent stereocontrol was observed during the cyclization. This approach provides a straightforward tool for further synthetic applications toward