Highly Stereoselective Glycosylation Reactions of Furanoside Derivatives via Rhenium(V) Catalysis was written by Casali, Emanuele;Sirwan, Othman T.;Dezaye, Ahmed A.;Chiodi, Debora;Porta, Alessio;Zanoni, Giuseppe. And the article was included in Journal of Organic Chemistry in 2021.Application In Synthesis of 5-Hexyldihydrofuran-2(3H)-one This article mentions the following:
A novel approach for the formation of anomeric carbon-functionalized furanoside systems was accomplished through the employment of an oxo-rhenium catalyst. The transformation boasts a broad range of nucleophiles including allylsilanes, enol ethers, and aromatics in addition to sulfur, nitrogen, and hydride donors, able to react with an oxocarbenium ion intermediate derived from furanosidic structures. The excellent stereoselectivities observed followed the Woerpel model, ultimately providing 1,3-cis-1,4-trans systems. In the case of electron-rich aromatic nucleophiles, an equilibration occurs at the anomeric center with the selective formation of 1,3-trans-1,4-cis systems. This anomalous result was rationalized through d. functional theory calculations Different oxocarbenium ions such as those derived from dihydro-isobenzofuran, pyrrolidine, and oxazolidine heterocycles can also be used as a substrate for the oxo-Re-mediated allylation reaction. In the experiment, the researchers used many compounds, for example, 5-Hexyldihydrofuran-2(3H)-one (cas: 706-14-9Application In Synthesis of 5-Hexyldihydrofuran-2(3H)-one).
5-Hexyldihydrofuran-2(3H)-one (cas: 706-14-9) belongs to esters. Esters are widespread in nature and are widely used in industry. In nature, fats are in general triesters derived from glycerol and fatty acids. Esters are responsible for the aroma of many fruits. Esters contain a carbonyl center, which gives rise to 120鎺?C閳ユ弲閳ユ彊 and O閳ユ弲閳ユ彊 angles. Unlike amides, esters are structurally flexible functional groups because rotation about the C閳ユ彊閳ユ弲 bonds has a low barrier. Their flexibility and low polarity is manifested in their physical properties; they tend to be less rigid (lower melting point) and more volatile (lower boiling point) than the corresponding amides. Application In Synthesis of 5-Hexyldihydrofuran-2(3H)-one
Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics