Synthesis of (1 → 2)-S-Linked Saccharides and S-Linked Glycoconjugates via a Palladium-G3-XantPhos Precatalyst Catalysis

Al‐Shuaeeb, Riyadh Ahmed Atto; Montoir, David; Alami, Mouâd; Messaoudi, Samir

doi:10.1021/acs.joc.7b00861

Cited by 48 publications

(38 citation statements)

References 40 publications

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“…The reaction is versatile (various aryl, akenyl, and alkynyl halides can be used), tolerates several functional groups (eg, –Br, –OTs, –OH, –CN, –CO 2 Me, –CONR 2 , C(Me)=NNHTs) and it is reproducible up to a multigram scale. The scope was then expanded to (1→2)‐ S ‐linked saccharides and S ‐linked glycoconjugates . The same method was also applied to heteroaryl bis‐glycosides, where N ‐glycosyl quinolin‐2‐ones (general structure 170 reported in Figure ) where a glycosyl unit is attached to a quinolin‐2‐one core (one of the most important heterocycle in medicinal chemistry) …”

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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“…Samir Messaoudi and his group [26] used 2-iodoglycals as coupling partners for the synthesis of thioglycosides (Scheme 12). They have used both αand β-glycosyl thiols in the Pd-catalyzed Buchwald-Hartwig-Migita cross-coupling approach under mild reaction conditions.…”

Section: Coupling Of Glycosyl Thiols With 2-iodo Glycalsmentioning

confidence: 99%

2‐Halo Glycals as “Synthon” for 2‐C‐Branched Sugar: Recent Advances and Applications in Organic Synthesis

2020

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Glycals are unsaturated sugars having an enolic double bond present inside the ring and act as a versatile synthon for the synthesis of natural products and biologically important molecules. The lone pair of endocyclic ring oxygen which is in conjugation with the enolic double bond alters the reactivity of both unsaturated carbons of glycals and directs the selectivity of the incoming group at a particular center. Since the enolic double bond is very much prone to undergo various types of reactions such as epoxidation, addition, formylation, nitration halogenation, etc.; and such type of activated glycals or the derivatives of glycal have been extensively utilized as a precursor for the synthesis of branched sugars. 2-haloglycals have emerged as an important building block for the functionalization at C-2 position of glycals via metal-catalyzed cross-coupling reactions such as Heck, Suzuki, Sonogashira and carbonylative cross-coupling reactions. In this review, we have summarized the recent progress on the utilization of 2-haloglycals for the synthesis of 2-C-branched sugars and further transformation of branched sugars into annulated sugars, heterocycles, and glycoconjugates.[a] Dr.

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“…In later reports Messaoudi and co-authors showed largely the potential application of this protocol. The authors started by highlighting the synthesis of (1→2)-S-Linked saccharides and S-linked glycoconjugates via a Pd-G3-XantPhos precatalyst catalysis [42] . This efficient methods allowed successfully the synthesis of various (1→2)-S-linked saccharides via a palladium precatalyst-catalyzed coupling of α-or β-mono-, di-, and polythiosugar derivatives with 2-iodoglycals.…”

Section: Scheme 14mentioning

confidence: 99%

Recent Advances in Transition‐Metal‐Catalyzed Functionalization of 1‐Thiosugars

2018

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Thioglycosides are valuable glycomimetic derivatives that have attracted much attention as mimetics of O-glycosides. Thioglycosides are among the most important glycomimetics reported to date due to their powerful activities. Owing to their importance, building up methods for their construction has drawn considerable attention. However, the classical methods of their synthesis presenting many shortcomings such as the use of harsh acidic media, and are generally limited in substrate scope. Therefore, metal-catalyzed coupling of thiosugars with halogenated electrophiles can be a superior and highly versatile approach to the sunthesis of thioglycosides. The central objective of this Focus Review is to highlight metal-catalyzed reactions for the creation of aromatic and heteroaromatic thioglycosides.

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Synthesis of (1 → 2)-S-Linked Saccharides and S-Linked Glycoconjugates via a Palladium-G3-XantPhos Precatalyst Catalysis

Cited by 48 publications

References 40 publications

Design and synthesis of glycomimetics: Recent advances

Design and synthesis of glycomimetics: Recent advances

2‐Halo Glycals as “Synthon” for 2‐C‐Branched Sugar: Recent Advances and Applications in Organic Synthesis

Recent Advances in Transition‐Metal‐Catalyzed Functionalization of 1‐Thiosugars

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