156672-99-0Relevant academic research and scientific papers
Homogeneous Gold-Catalyzed Glycosylations in Continuous Flow
Matthies, Stefan,McQuade, D. Tyler,Seeberger, Peter H.
supporting information, p. 3670 - 3673 (2015/08/18)
The use of versatile alkynyl-building blocks that are activated by gold(I)-catalysis is demonstrated to efficiently generate a variety of glycosides in continuous flow. The application of a continuous flow setting to gold(I)-catalyzed glycosylations enables very short reaction times and excellent control of the reaction conditions.
Evidence for cyclic bromonium ion transfer in electrophilic bromination of alkenes: Reaction of ω-alkenyl glycosides with aqueous N-bromosuccinimide
Rodebaugh, Robert,Fraser-Reid, Bert
, p. 7663 - 7678 (2007/10/03)
Evidence is provided to support the theory that intermolecular Br+ transfer from a cyclic bromonium ion to an alkene occurs readily and can indeed overwhelm alternative reaction pathways. In the course of a study to determine which ω-alkenyl glycosides could serve as glycosyl donors, it was found that upon treatment with N-bromosuccinimide (NBS) in aqueous acetonitrile, under conditions in which an n-pentenyl glycoside underwent oxidative hydrolysis to the corresponding hemi-acetal, allyl, butenyl, and hexenyl analogs gave bromohydrin addition products. It was further found that when pentenyl and hexenyl analogs were made to compete for an insufficient amount of NBS, the former reacted while the latter was apparently recovered unchanged. However, both reacted independently at similar rates. In addition, the phenomenon was found to be concentration dependent. These results are consistent with the intermolecular, non-degenerate transfer of Br+ from cyclic bromonium ion to alkene.
