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

**Authors:** Ivan Šnajdr, Kamil Parkan, Filip Hessler, Martin Kotora

PMC · DOI: 10.3762/bjoc.11.150 · 2015-08-10

## 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.

## Key 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.

## Linked entities

- **Chemicals:** ClCH2CH2Cl (PubChem CID 11), CuI (PubChem CID 104815), CH2Cl2 (PubChem CID 6344)

## Full-text entities

- **Diseases:** type II or III olefins (MESH:C536044)
- **Chemicals:** Alkenes (MESH:D000475), CuI (MESH:C073870), C (MESH:D002244), ethene (MESH:C036216), ethanol (MESH:D000431), ethyne (MESH:D000114), acetonitrile (MESH:C032159), 1,2-dichloroethane (MESH:C024565), ether (MESH:D004986), allyl amines (MESH:D000499), allyltrimethylsilane (MESH:C440774), Pd (MESH:D010165), diols (MESH:D011276), iodobenzene (MESH:C031905), CH2Cl2 (MESH:D008752), D-galactoses (MESH:D005690), styrenes (MESH:D013343), octafluorotoluene (MESH:C059211), H2O. (MESH:D014867), H2 (MESH:D006859), K2CO3 (MESH:C037593), carborane (-), saccharides (MESH:D002241), toluene (MESH:D014050)

## Figures

7 figures with captions in the complete paper: https://tomesphere.com/paper/PMC4578437/full.md

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Source: https://tomesphere.com/paper/PMC4578437