Stereo- and regioselective glycosylation with protection-less sugar derivatives: an alluring strategy to access glycans and natural products

Abstract

This review delivers insights for dedicated chemists into the development of efficient methods in accessing carbohydrates at a lower cost.

A novel fluorescent digitonin derivative for non-invasive skin cholesterol detection: potential application in atherosclerosis screening

“…Several teams are trying to synthesize single compounds of these substances, but current technology does not guarantee the introduction of uorophores on specic hydroxyl groups. [21][22][23][24] We hope that this method will be established as organic chemistry develops further. Although we could not characterize FDD by 1 H NMR and 13 C NMR, we separated and puried FDD by preparative high-performance liquid chromatography, and obtained FDD with a molecular weight of 1803.8 (one digitonin connected to one uorescent group), and the measured purity was 98.99%.…”

A Chiral Copper Catalyzed Site‐Selective O‐Alkylation of Carbohydrates

“…Carbohydrates play an important physiological role in life and are always important part of many drugs and materials [1–4] . The synthesis of high value‐added carbohydrates and site‐selective modification of functional oligosaccharide still remains the most important research topics for carbohydrate chemistry [5–12] . Since carbohydrates have several similarly active hydroxyl groups, highly selective modification of the hydroxyl groups becomes more and more important [13–15] .…”

Glycosyl Exchange of Unactivated Glycosidic Bonds: Suppressing or Embracing Side Reactivity in Catalytic Glycosylations

“…[3] This understanding of the crucial role of carbohydrate building blocks has led to a surge in demand for enabling tools, answered by significant advances in mass spectrometry of complex mixtures [4] and labeling approaches to image or detect carbohydrates expressed on cell surfaces. [5] Various perspectives [6] and funding agencies [7] have recognized that the synthesis of complex carbohydrates is a limiting step for advancement in the glycosciences due to difficulties in controlling regio- [8] and diastereoselectivity [9] as well as challenges in preparing the appropriately protected building blocks. [10] A recent focus of our lab is the development of efficient catalytic methods for glycosylation, using the combination of glycosyl fluorides as the glycosyl donor and silyl ethers as the glycosyl acceptor.…”