Cross-metathesis reaction of α- and β-vinyl C-glycosides with alkenes
Ivan Šnajdr, Kamil Parkan, Filip Hessler, Martin Kotora
TL;DR
This paper studies chemical reactions involving sugar derivatives and alkenes, finding optimal conditions for efficient product formation.
Contribution
A new method for preparing α- and β-vinyl C-deoxyribosides and optimized cross-metathesis conditions are introduced.
Findings
Cross-metathesis of α- and β-vinyl C-deoxyribosides with terminal alkenes in ClCH2CH2Cl yields good results.
α-vinyl C-galactoside cross-metathesis requires CuI in CH2Cl2 for high product yields.
A simple preparation method for α- and β-vinyl C-deoxyribosides was developed.
Abstract
Cross-metathesis of α- and β-vinyl C-deoxyribosides and α-vinyl C-galactoside with various terminal alkenes under different conditions was studied. The cross-metathesis of the former proceeded with good yields of the corresponding products in ClCH2CH2Cl the latter required the presence of CuI in CH2Cl2 to achieve good yields of the products. A simple method for the preparation of α- and β-vinyl C-deoxyribosides was also developed. In addition, feasibility of deprotection and further transformations were briefly explored.
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Taxonomy
TopicsUrbanism, Landscape, and Tourism Studies