118918-76-6

Usage

Uses

Used in Pharmaceutical Industry:
(2S,5R)-2-phenyl-1-aza-3-oxabicyclo<3.3.0>octan-8-one is used as a potential pharmaceutical candidate for [application reason] due to its unique structure and properties.
Used in Chemical Industry:
(2S,5R)-2-phenyl-1-aza-3-oxabicyclo<3.3.0>octan-8-one is used as a potential chemical intermediate or building block for [application reason] in the synthesis of other organic compounds, given its specific structural features.

Upstream product

• 64700-65-8 methyl (2R)-pyroglutamate 
• 68766-96-1 ethyl (R)-2-pyrrolidone-5-carboxylate 
• 13107-55-6 D-glutamic acid diethyl ester 
• 6893-26-1 D-Glutamic acid 
• 66673-40-3 (R)-5-hydroxymethylpyrrolidin-2-one 
• 100-52-7 benzaldehyde 
• 62400-75-3 pyroglutamol 

Downstream Products

• 134037-90-4 (3S,7aR)-3-Phenyl-6-phenylselanyl-tetrahydro-pyrrolo[1,2-c]oxazol-5-one 
• 1311406-94-6 (3S,6R,7aR)-6-hydroxy-3-phenyltetrahydropyrrolo[1,2-c]oxazol-5(3H)-one 
• 1311406-95-7 C₁₂H₁₃NO₃ 
• 1311406-96-8 C₁₇H₁₆N₆O₂ 
• 1426125-48-5 C₁₉H₂₀N₂O₂ 
• 1426125-57-6 C₁₉H₂₄N₆O₂*C₂H₂O₄ 
• 1426125-49-6 C₁₉H₂₀N₂O₂*C₂H₂O₄ 
• 1426125-50-9 C₁₉H₂₄N₂O 
• 1334700-32-1 (-)-(3R,4R)-1-benzyl-4-(benzylamino)piperidin-3-ol 
• 1426125-45-2 tert-butyl N-benzyl-N-[(3R,4R)-3-hydroxypiperidin-4-yl]carbamate 
• 118868-00-1 (2S,5R,6S,7S)-2-phenyl-6,7-dihydroxy-1-aza-3-oxabicyclo<3.3.0>octan-8-one 
• 118868-01-2 (2S,5R,6S,7S)-2-phenyl-6,7-(isopropylidene)dioxy-1-aza-3-oxabicyclo<3.3.0>octan-8-one 
• 77674-99-8 6-<<1(S)-<3(S),4-dihydro-8-hydroxy-1-oxo-1H-2-benzopyran-3-yl>-3-methylbutyl>amino>-4(S),5(S)-dihydroxy-6-oxo-3(S)-ammoniohexanoate 
• 154774-34-2 (3S,7aR)-7a-((S)-1-Hydroxy-2-methyl-propyl)-6-methyl-3-phenyl-1,7a-dihydro-pyrrolo[1,2-c]oxazol-5-one 

Relevant academic research and scientific papers

Synthesis of [(3S,5R)-3-Hydroxy-5-methylpiperidin-1-yl](2-methylpyridin-3-yl)methanone

Abstract: There remain challenges for effectively synthesizing heterocycles containingboth piperidine and pyridine rings, mainly due to the inefficient syntheticprocess mostly requiring long reaction times. This paper reports a simple andefficient method

Structural prerequisites for receptor binding of helicokinin I, a diuretic insect neuropeptide from helicoverpa zea

In insects essential physiological processes such as muscle activity or water balance are controlled by neuropeptides. However, owing to their metabolic instability and adverse physicochemical properties peptides are unsuited as crop protection agents. Helicokinin I, a diuretic neuropeptide of cotton pest Helicoverpa zea represents a most promising target for the design of neuropeptide mimetics. Several helicokinin analogues containing scaffolds with varying rigidity and different orientations of the N- and C-terminal peptide chains were synthesized and tested for receptor binding. Additional conformational analyses by NMR spectroscopy in a membrane-mimicking environment together with MD simulations provide a deeper insight into the structural requirements for receptor binding and explain the remarkable activity of a macrocyclic helicokinin I derivative. A delicate balance of rigidity and flexibility makes the difference between activity and inactivity. Detailed conformational studies of analogues of the diuretic insect-neuropeptide helicokinin I containing diverse cyclic scaffolds with different flexibility and orientation of the N- and C-termini provide a better understanding of the structural requirements for receptor binding. Copyright

Evolution of the process for the preparation of a selective erbb vegf receptor inhibitor

An efficient synthetic route to the potent and selective ErbB VEGF receptor inhibitor, BMS-690514 (1) is described. Strategic modifications in both approach and procedure addressed several issues, which led to a safe, efficient, and economical process for the preparation of multi-kilogram quantities of 1. The convergent route involves alkylation of a suitably protected (3R,4R)-4-aminopiperidin-3-ol with the triethyl(alkyl)ammonium salt of a functionalized pyrrolotriazine 3a followed by deprotection to provide 1 as the crystalline free base. Georg Thieme Verlag Stuttgart - New York.

Synthesis of 3-guaninyl- and 3-adeninyl-5-hydroxymethyl-2-pyrrolidinone nucleosides

l- And d-glutamic acids, as well as trans-4-hydroxy-l-proline, are converted to the corresponding 3-guaninyl-5-hydroxymethyl-2-pyrrolidinone (4) or 3-adeninyl-5-hydroxymethyl-2-pyrrolidinone (5) nucleoside analog. The protecting group used to block the lactam nitrogen in key intermediates has a significant effect on the diastereoselectivity of the coupling reaction with adenine or guanine.

Efficient total synthesis of AI-77-B, a gastroprotective substance from Bacillus pumilus AI-77

First total synthesis of AI-77-B (1), a gastroprotective substance from Bacillus pumilus AI-77, was achieved in a stereoselective and convergent manner. In this synthesis, the dihydroisocoumarin part 2 was constructed in one step through 1,2-addition of the benzylic anion 17b to Boc-L-leucinal 7b. The hydroxy amino acid 4 was elaborated from (R)-glutamic acid in a highly stereoselective manner. Condensation of 2·HCl and 4, intramolecular Pinner reaction, followed by mild hydrolysis afforded AI-77-B (1).

A MESO SPECIFIC REACTION

Acid-catalyzed condensation of optically pure 5-(hydroxymethyl)-2-pyrrolidinone, 2, with benzaldehyde gives only a monomeric optically active oxazolidine, 3, while under the same conditions, racemic 2 gives only a meso centrosymmetric compound 4 - a dimer of racemic 3.This meso specific reaction serves as a highly efficient method for increasing the optical purity of the generally useful chiral building blocks 2 and 3.