3‐Aminodeoxypyranoses in Glycosylation: Diversity‐Oriented Synthesis and Assembly in Oligosaccharides

Zeng, Jing; Sun, Guangfei; Yao, Wang; Zhu, Yangbin; Wang, Ruobin; Cai, Lei; Liu, Ke; Zhang, Qian; Liu, Xuewei; Wan, Qian

doi:10.1002/anie.201700178

Cited by 59 publications

(37 citation statements)

References 73 publications

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“… 102 On the other hand, Zeng, Wan, and co-workers found that fluorides were not the optimal leaving group for coupling a ristosamine donor to C-4 of a galactose acceptor. 103 As a consequence, many other classes of dexoyglycosyl donors have been developed, often mirroring donors used in conventional glycosylation reactions.…”

Section: Direct Synthesismentioning

confidence: 99%

Methods for 2-Deoxyglycoside Synthesis

2018

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Deoxy-sugars often play a critical role in modulating the potency of many bioactive natural products. Accordingly, there has been sustained interest in methods for their synthesis over the past several decades. The focus of much of this work has been on developing new glycosylation reactions that permit the mild and selective construction of deoxyglycosides. This Review covers classical approaches to deoxyglycoside synthesis, as well as more recently developed chemistry that aims to control the selectivity of the reaction through rational design of the promoter. Where relevant, the application of this chemistry to natural product synthesis will also be described.

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Section: Direct Synthesismentioning

confidence: 99%

Methods for 2-Deoxyglycoside Synthesis

2018

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“…A 10 L sample was injected for each analysis. 16 Potassium carbonate (0.5 g, 3.6 mmol, 0.1 equiv) was added to a solution of tri-O-acetyl-D-glucal (10.0 g, 36.7 mmol, 1.0 equiv) in MeOH (70 mL) and the mixture was stirred at room temperature for 4 h. After completion, the mixture was filtered through Celite and concentrated on a rotary evaporator to give D-glucal as a viscous oil in quantitative yield (~5.3 g). The obtained crude product (5.3 g, 36.4 mmol) was dissolved in a mixture of dry CH 2 Cl 2 (73 mL) and dry pyridine (73 mL), cooled to 0 °C, and treated with p-toluenesulfonyl chloride (10.4 g, 54.6 mmol, 1.5 equiv).…”

Section: Syn Thesismentioning

confidence: 99%

Palladium-Catalyzed One-Pot Stereospecific Synthesis of 2-Deoxy Aryl C-Glycosides from Glycals and Anilines in the Presence of tert-Butyl Nitrite

Singh¹,

Venkatesh²,

Kandasamy

2019

Synthesis

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The palladium-catalyzed one-pot synthesis of 2,3-deoxy-3-keto aryl C-glycosides is achieved from glycals and anilines in the presence of tert-butyl nitrite and aqueous HBF4 under mild conditions. This one-pot method stereospecifically provides α- and β-aryl glycosides (≥19:1 by NMR) in good yields at room temperature. The configuration at the C-3 position in the glycal determines the anomeric selectivity (i.e., α or β) of the desired products.

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“…Bacterial monosaccharides can feature diversely substituted amino groups, deoxy centers, carbonyl groups, and tetrasubstituted tertiary carbon atoms at various positions on the carbohydrate ring. Tertiary‐ C sugars can be found in various natural products, having attractive biological properties [7–10] . Often these tertiary C‐atoms are substituted with a small alkyl group, commonly a methyl substituent, but more complex architectures in which functionalized alkyl chains are attached can be found as well.…”

Section: Introductionmentioning

confidence: 99%

Reactivity–Stereoselectivity Mapping for the Assembly of Mycobacterium marinum Lipooligosaccharides

et al. 2020

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The assembly of complex bacterial glycans presenting rare structural motifs and cis-glycosidic linkages is significantly obstructed by the lack of knowledge of the reactivity of the constituting building blocks and the stereoselectivity of the reactions in which they partake. We here report a strategy to map the reactivity of carbohydrate building blocks and apply it to understand the reactivity of the bacterial sugars, caryophyllose, a rare C12-monosaccharide, containing a characteristic tetrasubstituted stereocenter. We mapped reactivity-stereoselectivity relationships for caryophyllose donor and acceptor glycosides, by a systematic series of glycosylations in combination with the detection and characterization of different reactive intermediates using experimental and computational techniques. The insights garnered from these studies enabled the rational design of building blocks with the required properties to assemble mycobacterial lipooligosaccharide fragments of M. marinum.

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3‐Aminodeoxypyranoses in Glycosylation: Diversity‐Oriented Synthesis and Assembly in Oligosaccharides

Cited by 59 publications

References 73 publications

Methods for 2-Deoxyglycoside Synthesis

Methods for 2-Deoxyglycoside Synthesis

Palladium-Catalyzed One-Pot Stereospecific Synthesis of 2-Deoxy Aryl C-Glycosides from Glycals and Anilines in the Presence of tert-Butyl Nitrite

Reactivity–Stereoselectivity Mapping for the Assembly of Mycobacterium marinum Lipooligosaccharides

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