725690-99-3Relevant academic research and scientific papers
Highly stereoselective addition of organozinc reagents to pentopyranose derived glycals: Effect of protecting group and assignment of C-glycoside stereochemistry
Cook, Matthew J.,Fletcher, Matthew J. E.,Gray, Diane,Lovell, Peter J.,Gallagher, Timothy
, p. 5085 - 5092 (2007/10/03)
The nucleophilic addition of ethyl 3-propionylzinc iodide to a variety of differently protected pentopyranose derived D-glycals 6a-g proceeds with good to high levels of diastereoselectivity to provide the corresponding β-C-glycosides 7. The stereochemistry of the para-nitrobenzoate derivative 7d has been confirmed by X-ray crystallography, and the stereochemistry of the other β-C-glycoside products has been correlated to 7d. The stereochemical outcome observed supports the earlier suggestion by Isobe that through-space effects are important in stabilising and controlling the reactivity of the intermediate oxonium species represented by 11.
