Palladium catalyzed decarboxylative β-<i>C</i>-glycosylation of glycals with oxazol-5-(4<i>H</i>)-ones as acceptors

Ding, Wei-Yi; Liu, Huan-Huan; Cheng, Jun Kee; Yao, Hui; Xiang, Shao‐Hua; Tan, Bin

doi:10.1039/d2qo01308h

Cited by 10 publications

(3 citation statements)

References 78 publications

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“…Previously various research groups demonstrated the synthesis of C-glycosides using ring-closing metathesis, [55] hetero-Diels-Alder reaction, [56] and Stille-type cross-coupling [57] reactions with poor diastereoselectivity with undesired side products. In recent years, the synthesis of C-aryl glycosides through metal-catalyzed CÀ H functionalization has been recognized as an efficient stereoselective strategy and attracted extensive attention by chemists [58][59][60] due to its steps and atomic economy which minimize or avoid the generation of waste.…”

Section: Metal-catalyzed Cà H Functionalizationmentioning

confidence: 99%

Recent Advances and Strategies towards Synthesis of Indolyl and Tryptophan‐C‐Glycoside Scaffolds

Sangwan,

Azeem,

Kumar Mandal

2024

Adv Synth Catal

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Recently, C‐glycosidic bonds have emerged as pivotal elementary units present in many naturally occurring alkaloids as well as in pharmaceutically active molecules. Because of the stability and great utility of C‐glycosides, synthetic approaches en route to the C‐C bond formation have gradually become a center of attraction in carbohydrate chemistry. Towards these researches, C‐glycosylation with heteroaryl moieties like indole, and tryptophan can remarkably expand the functional and structural evolution, which has great value for medicinal chemists and chemical biologists. The indolyl and tryptophan‐C‐glycosides have unique structures and biological activities that have attracted a number of synthetic studies. Therefore, these motifs have possessed an extensive interest in the direction of efficient synthesis. Herein, this review systematically summarizes the classical approaches to C‐heteroaryl glycosides mainly focusing on indole and tryptophan synthesis. Furthermore, highlighted the recently developed metal‐catalyzed C‐H functionalization and photoinduced cross‐coupling strategies that aim to control the regioselectivity and diastereoselectivity of the reaction in carbohydrate chemistry. In view of reaction type, mechanism, and status, this review will cover the synthesis of indole and tryptophan C‐heteroaryl glycosides with diverse regio‐ and diastereoselectivity from four perspectives which include a) conventional approach, b) heterocyclization and C‐glycosylation sequence, c) metal‐catalyzed C‐H functionalization, and d) photoinduced cross‐coupling. 1. Introduction 2. Strategies for the synthesis of indolyl and tryptophan‐C‐glycosides 2.1. Conventional approach 2.2. Heterocyclization and C‐glycosylation sequence 2.3. Metal‐catalyzed C‐H functionalization 2.4. Photoinduced cross‐coupling 3. Summary and Outlook

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Section: Metal-catalyzed Cà H Functionalizationmentioning

confidence: 99%

Recent Advances and Strategies towards Synthesis of Indolyl and Tryptophan‐C‐Glycoside Scaffolds

Sangwan,

Azeem,

Kumar Mandal

2024

Adv Synth Catal

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“…After the success of the synthesis of -C-glycosides, our subsequent research explored the stereoselective synthesis of -C-glycosides. 42 Oxazol-5(4H)-ones were employed as the glycosyl acceptors, which were also direct precursors to amino acids. Under the palladium catalyst and bulky phosphine ligands, oxazol-5(4H)-ones reacted with 3,4-O-carbonate-D-galactal to form -C-glycosides stereoselectively.…”

Section: Scheme 6 Open-air Stereoselective Construction Of C-aryl Gly...mentioning

confidence: 99%

Highly Regio-/Stereoselective Synthesis of Carbohydrates with Unsaturated Glycosyl Donors under Mild Conditions

Wang,

Huang,

Yao

et al. 2024

Synlett

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Carbohydrates and their conjugates play important roles in life activities and drug development. Our group was committed to the general and effective glycosylation methods and their application in chemical biology using unsaturated glycosyl donors. In the past five years, we have reported several synthetic strategies with high stereoselectivity and milder conditions compared with previous works. In particular, high chemo-/regio- and stereoselective O-glycosylation, C-glycosylation and S-glycosylation could be achieved via palladium catalysis under open-air conditions at room temperature. In this account, we will introduce our research progress in constructing four types of glycosides. 1 Introduction 2 Stereoselective synthesis of O-glycosides 3 Stereoselective synthesis of C-glycosides 4 Stereoselective synthesis of N-glycosides 5 Stereoselective synthesis of S-glycosides 6 Conclusion

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“…Therefore, the stereoselective synthesis of 2-deoxythioglycosides is still highly challenging. In view of our long-standing interest in exploring 3,4-O-carbonate-glycal donors [21][22][23][24][25][26][27], herein, we report an effective and stereoselective 2-deoxythioglycosylation catalyzed by the commercially available catalyst silver trifluoromethanesulfonate (AgOTf) as shown in Scheme 1c. The target α-2-deoxythiosugars were able to be obtained in good yields with high stereoselectivity under mild conditions.…”

Section: Introductionmentioning

confidence: 99%

Stereoselective Synthesis of 2-Deoxythiosugars from Glycals

et al. 2022

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2-deoxythiosugars are more stable than 2-deoxysugars occurring broadly in bioactive natural products and pharmaceutical agents. An effective and direct methodology to stereoselectively synthesize α-2-deoxythioglycosides catalyzed by AgOTf has been developed. Various alkyl thiols and thiophenols were explored and the desired products were formed in good yields with excellent α-selectivity. This method was further applied to the syntheses of S-linked disaccharides and late-stage 2-deoxyglycosylation of estrogen, L-menthol, and zingerone thiols successfully.

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Palladium catalyzed decarboxylative β-C-glycosylation of glycals with oxazol-5-(4H)-ones as acceptors

Abstract: Despite the increased importance of C-glycosides in biochemistry, strategy to forge C-glycosidic bond stereoselectively is inherently more challenging than the O- and N- counterparts. We describe here a β-C-glycosylation of...

Cited by 10 publications

References 78 publications

Recent Advances and Strategies towards Synthesis of Indolyl and Tryptophan‐C‐Glycoside Scaffolds

Recent Advances and Strategies towards Synthesis of Indolyl and Tryptophan‐C‐Glycoside Scaffolds

Highly Regio-/Stereoselective Synthesis of Carbohydrates with Unsaturated Glycosyl Donors under Mild Conditions

Stereoselective Synthesis of 2-Deoxythiosugars from Glycals

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