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Cross-metathesis reaction of ?- and ?-vinyl C-glycosides with alkenes.

ABSTRACT: Cross-metathesis of ?- and ?-vinyl C-deoxyribosides and ?-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 ?- and ?-vinyl C-deoxyribosides was also developed. In addition, feasibility of deprotection and further transformations were briefly explored.

SUBMITTER: Snajdr I

PROVIDER: S-EPMC4578437 | biostudies-other | 2015

REPOSITORIES: biostudies-other

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Cross-metathesis reaction of α- and β-vinyl C-glycosides with alkenes.

Šnajdr Ivan I Parkan Kamil K Hessler Filip F Kotora Martin M

Beilstein journal of organic chemistry 20150810

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 transformati ...[more]

PMID: 26425194

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