scholarly journals (2S,3R,6R)-2-[(R)-1-Hydroxyallyl]-4,4-dimethoxy-6-methyltetrahydro-2H-pyran-3-ol

Molbank ◽  
10.3390/m1140 ◽  
2020 ◽  
Vol 2020 (2) ◽  
pp. M1140
Author(s):  
Jack Bennett ◽  
Paul Murphy

(2S,3R,6R)-2-[(R)-1-Hydroxyallyl]-4,4-dimethoxy-6-methyltetrahydro-2H-pyran-3-ol was isolated in 18% after treating the glucose derived (5R,6S,7R)-5,6,7-tris[(triethylsilyl)oxy]nona-1,8-dien-4-one with (1S)-(+)-10-camphorsulfonic acid (CSA). The one-pot formation of the title compound involved triethylsilyl (TES) removal, alkene isomerization, intramolecular conjugate addition and ketal formation. The compound was characterized by 1H and 13C NMR spectroscopy, ESI mass spectrometry and IR spectroscopy. NMR spectroscopy was used to establish the product structure, including the conformation of its tetrahydropyran ring.

Author(s):  
Darya S. Volkova ◽  
Anna S. Kositsyna ◽  
Kukushkin, Alexey A. Kukushkin ◽  
Evgeniy V. Root

А para-chlorophenyl substituent was firstly obtained into the structure of pyridyl-substituted 4-nitrosopyrazole by cyclocondensation of hydrazine hydrate with the corresponding isonitroso-β-dicarbonyl compounds. The structure of previously unknown 3(5)-(4-chlorophenyl)-5(3)-pyridine-(3(4))-yl-4-nitroso-1H-pyrazoles and previously obtained 3(5)-alkyl(aryl)-5(3)-pyridine-(3(4))-yl-4-nitroso-1H-pyrazoles is proved and studied in detail by modern methods of analysis: mass spectrometry, 1H- and 13C NMR-spectroscopy


2021 ◽  
Vol 3 ◽  
pp. 119-127
Author(s):  
G.M. Baisarov ◽  
◽  
S.M. Adekenov ◽  

The reaction of 5-hydroxy-7-methoxy-2-phenylchroman-4-one with dibromoalkanes in acetone in the presence of potassium carbonate proceeds according to the Michael’s retro-reaction O-alkylation and leads to the formation of the corresponding 2-(bromo-alkoxy) chalcones. The structure of the synthesized compounds was confirmed by IR-, 1H- and 13C-NMR spectroscopy. The cytotoxic, hepatoprotective and anti-inflammatory effects of chalcone derivatives (2-3) were studied for the first time in vitro and in vivo.


Sign in / Sign up

Export Citation Format

Share Document