Versatile Glycosyl Sulfonates in β‐Selective C‐Glycosylation

Abstract

C‐Glycosides are both a common motif in many bioactive natural products and important glycoside mimetics. We demonstrate that activating a hemiacetal with a sulfonyl chloride, followed by treating the resultant glycosyl sulfonate with an enolate results in the stereospecific construction of β‐linked C‐glycosides. This reaction tolerates a range of acceptors and donors, including disaccharides. The resulting products can be readily derivatized into C‐glycoside analogues of β‐glycoconjugates, including C‐disaccharide mimetics.

Influence of protecting groups on O- and C-glycosylation with neuraminyl and ulosonyl dibutylphosphates

“…It remains possible that the 5-desamino-5-isothiocyanato and 5-azido modifications may yet prove suitable for use in α-selective C-glycosylations as and when chemistry is developed for the synthesis of comparable donors with less activated leaving groups. 28…”

Effects of Medium- and Long-Chain Structured Triacylglycerol on the Therapeutic Efficacy of Vitamin D on Ulcerative Colitis: A Consideration for Efficient Lipid Delivery Systems

“…Chen et al. identified that, if different carriers are used to deliver fat-soluble substances, there are significant differences in the composition and distribution of fat-soluble nutrient metabolite. , The nanoparticle beta-carotene tends to be stored in adipocytes. In contrast, the nanoemulsion beta-carotene tends to be metabolized into retinol and stored in the liver, leading to different effects on high-fat stimulation.…”

Development of a Cryogenic Flow Reactor to Optimize Glycosylation Reactions Based on the Active Donor Intermediate

“…This aim is challenging because the selectivity in these reactions is dictated by a number of factors, including temperature, concentration, method of activation, and the reactivity of coupling partners . While S N 2-like kinetics for chemical glycosylation reactions have been reported by several research groups, ,− obtaining highly selective glycosylation reactions that can be generalized to a range of coupling partners remains difficult. In many cases, these reactions are initiated at cryogenic temperatures and are then allowed to slowly warm to ambient temperature .…”