40246-31-9Relevant academic research and scientific papers
Carbohydrate-Derived 3,2-Enolones in the Base-Catalyzed Rearrangement to Highly Functionalized C4-Quaternary 4-Hydroxy-2-cyclopentenones
Borowski, Daniel,Oechsner, Regina M.,Jürgens, Eva,Ziegler, Thomas
, p. 4490 - 4499 (2017/08/23)
3,4,6-O-benzylated β-2-ulosides were subjected to 3,4-elimination, providing carbohydrate-derived 3,2-enolones. Reaction of these enolones under basic conditions in polar aprotic solvents afforded highly functionalized racemic 5-alkoxy-2-benzyloxy-4-benzyloxymethyl-4-hydroxy-2-cyclopentenones. The influence of the nature of the base as well as solvent effects were investigated. The rearrangement products obtained from this reaction exhibit a 4-hydroxy-C4-quaternary stereogenic center. In contrast, the rearrangement of comparable dihydropyran-3-ones was reported to furnish the C5-quaternary 5-hydroxy-2-cyclopentenones. Plausible mechanisms for the described rearrangement and subsequent isomerization processes are given.
Experimental evidence on the hydroxymethyl group conformation in alkyl β-D-mannopyranosides
Mayato, Carlos,Dorta, Rosa,Vazquez, Jesus
, p. 2385 - 2397 (2007/10/03)
A rotational population study of the hydroxymethyl group of alkyl β-D-mannopyranosides was performed by means of CD and NMR spectroscopy. Three different benzyl, acetyl, and p-bromobenzoyl series of alkyl β-D-mannopyranosides with different chiral and non
