Glycosyl Stille Cross-Coupling with Anomeric Nucleophiles – A General Solution to a Long-Standing Problem of Stereocontrolled Synthesis of C-Glycosides

Zhu, Feng; Yang, Tianyi; Walczak, M

doi:10.1055/s-0036-1589020

Cited by 24 publications

(2 citation statements)

References 22 publications

(24 reference statements)

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“…Anomeric stannanes are configurationally stable nucleophiles that can be stored and manipulated under ambient conditions without loss of stereochemical integrity, even after extended periods of time (6 months at room temperature or 1 year at −20°C). They can be easily prepared starting from the corresponding glycal 130 , affording either 1,2‐ cis or 1,2‐ trans glycosides, thus allowing formation of both C(1) anomers …”

Section: Exocyclic Oxygen Replacementmentioning

confidence: 99%

Design and synthesis of glycomimetics: Recent advances

Tamburrini

Colombo

Bernardi

2019

Medicinal Research Reviews

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In the past few decades, our understanding of glycan information‐encoding power has notably increased, thus leading to a significant growth also in the design and synthesis of glycomimetic probes. Combining data from multiple analytical sources, such as crystallography, nuclear magnetic resonance spectroscopy, and other biophysical methods (eg, surface plasmon resonance and carbohydrate microarrays) has allowed to shed light on the key interaction events between carbohydrates and their protein‐targets. However, the low metabolic stability of carbohydrates and their high hydrophilicity, which translates in low bioavailability, undermine their development as drugs. In this framework, the design of chemically modified analogues (called carbohydrate mimics or glycomimetics) appears as a valid alternative for the development of therapeutic agents. Glycomimetics, as structural and functional mimics of carbohydrates, can replace the native ligands in the interaction with target proteins, but are designed to show enhanced enzymatic stability and bioavailability and, possibly, an improved affinity and selectivity toward the target. In the present account, we specifically focus on the most recent advances in the design and synthesis of glycomimetics. In particular, we highlight the efforts of the scientific community in the development of straightforward synthetic procedures for the preparation of sugar mimics and in their preliminary biological evaluation.

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Section: Exocyclic Oxygen Replacementmentioning

confidence: 99%

Design and synthesis of glycomimetics: Recent advances

Tamburrini

Colombo

Bernardi

2019

Medicinal Research Reviews

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“…In general, the synthesis of C-glycosides can be categorized by reactive intermediate at the anomeric carbon. Reactivity has been established for formally cationic, anionic, and radical based intermediates . Depending on the method used, various stereoisomers can be generated.…”

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confidence: 99%

Diverse Synthesis of C-Glycosides by Stereoselective Ni-Catalyzed Carboboration of Glycals

Lyu,

Jacobo,

Brown

2024

J. Am. Chem. Soc.

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C-Glycosides are important structures that are common to natural products and pharmaceutical agents. Established methods for their synthesis involve the reaction of an activated anomeric carbon. In this study, we report a conceptually new approach that involves the stereoselective Ni-catalyzed carboboration of glycals. In these reactions, not only is a C−C bond formed at the anomeric carbon, but a synthetically useful C−B bond is also installed. Upon C−B oxidation, differentially protected Cglycosides to be formed. In addition, stereospecific manipulation of the C−B bond leads to diverse C-glycosides. Finally, we report the application of this method in the synthesis of established C-glycosides, such as C-glycosyl amino acids, as well as a strategy to make all possible diastereomers at C1 and C2.

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