25874-19-5Relevant academic research and scientific papers
An efficient method for the synthesis of pyranoid glycals
Chen, Heshan,Xian, Ting,Zhang, Wan,Si, Wenshuai,Luo, Xiaosheng,Zhang, Bo,Zhang, Meiyu,Wang, Zhongfu,Zhang, Jianbo
supporting information, p. 42 - 46 (2016/07/06)
A simple and efficient procedure was designed for the preparation of pyranoid glycals. In a novel fashion, a series of protected glycopyranosyl bromides underwent reductive elimination in the presence of zinc dust and ammonium chloride in CH3CN at 30-60 °C. The corresponding glycals were obtained with excellent isolated yields (72-96%) in a short time (20-50 min). Furthermore, the transformation was compatible with different protection patterns and conveniently scalable (86% for 45 g acetobromoglucose) which made it very applicable in organic synthesis.
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.
GLYCALS IN STEREOSPECIFIC SYNTHESIS. II. DI-O-BENZYL-L-ARABINAL AND DI-O-BENZOYL-L-ARABINAL IN THE SYNTHESIS OF SATURATED AND UNSATURATED TERMINAL EPOXIDES
Tolstikov, A. G.,Khakhalina, N. V.,Savateeva, E. E.,Spirikhin, L. V.,Odinokov, V. N.,Tolstikov, G. A.
, p. 706 - 710 (2007/10/02)
The acid opening of di-O-benzyl-L-arabinal and di-O-benzoyl-L-arabinal, catalyzed by mercuric sulfate, is the key stage in the synthesis of chiral dihydroxy compounds with selectively protected hydroxy functions.They were used for the production of saturated and unsaturated terminal epoxides, which are of potential interest as chiral units in the convergent synthesis of biologically active compounds.
