Palladium‐Catalyzed Stereospecific <i>S</i>‐Glycosylation by Allylic Substitution

Wang, Yanyan; Cao, Zhang; Wang, Nengzhong; Liu, Mingguo; Wang, Long; Huang, Nianyu

doi:10.1002/adsc.202300129

Cited by 3 publications

(1 citation statement)

References 58 publications

(19 reference statements)

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“…To the best of our knowledge, phosphine-catalyzed annulation reactions have been well demonstrated as powerful synthetic methods for the efficient construction of ring structures . In conjunction with our interest in catalysis, especially phosphine catalysis, we envisioned that the spiro[benzofuran-cyclohexane] skeletons may be constructed via a phosphine-catalyzed [2 + 4] annulation between benzofuran-derived azadienes (BDAs) and acidic hydrogen-tethered allyl carbonates (Scheme ).…”

Section: Introductionmentioning

confidence: 99%

Highly Regio- and Diastereoselective Phosphine-Catalyzed [2 + 4] Annulation of Benzofuran-Derived Azadienes with Allyl Carbonates: Access to Spiro[benzofuran-cyclohexanes]

Huang,

Tan,

Wang

et al. 2023

J. Org. Chem.

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A novel highly regio- and diastereoselective phosphine-catalyzed [2 + 4] annulation of benzofuran-derived azadienes (BDAs) with acidic hydrogen-tethered allyl carbonates has been developed ingeniously. A range of functionalized spiro[benzofuran-cyclohexane] derivatives with two consecutive stereocenters were smoothly obtained in moderate to excellent yields under mild reaction conditions from readily available materials. Moreover, this method is a practical and scalable strategy that creates the core structural motif of the fungistatic drug, griseofulvin.

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Section: Introductionmentioning

confidence: 99%

Highly Regio- and Diastereoselective Phosphine-Catalyzed [2 + 4] Annulation of Benzofuran-Derived Azadienes with Allyl Carbonates: Access to Spiro[benzofuran-cyclohexanes]

Huang,

Tan,

Wang

et al. 2023

J. Org. Chem.

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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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Regio- and Stereo-selective Synthesis of 1β-/3R-Aryl Thiosugar

Zou,

Wang,

Yao

et al. 2024

Chinese Journal of Organic Chemistry

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Thiosugars have attracted much attention in the field of pharmaceuticals because of their excellent biological activities, and chemical synthesis is an important way to obtain thiosugars. Using 6-O-diphenylphosphoryl-3,4-O-carbonate-D-galactal and thiophenols as starting materials, the regio-and stereo-selective syntheses of 1β-/(3R)-aryl thiosugars were controlled with NiBr2 and Pd2(dba)3 catalysts, respectively. The structures of the target compounds were characterized by nuclear magnetic resonance, high-resolution mass spectrometry and single crystal X-ray diffraction. This method exhibited favourable compatibility with various functional groups substituted thiophenols, which could be used for the structural modification of active natural products. The research work is help for the rapid construction of the compound library of 1β-/(3R)-aryl thiosugars for drug discovery. Keywords Pd catalysis; Ni catalysis; D-galactal; thiosugar; synthesis 近年来, 糖类化合物作为生物成像的载体 [1] 、修饰 DNA 和蛋白质的重要物质 [2] 和细胞培养保存的介质 [3] , 在生物领域被广泛研究. 硫代糖类化合物作为氧糖苷的类似物, 具有更广泛的生物活性和更好的稳定性. 细胞表面的一些糖类承担着免疫识别的重要作用, 硫代糖已经被证明是酶系统中碳水化合物与蛋白质之间相互作用的重要工具 [4] . 硫代低聚糖 S-Galp(α1→3)Galp 还可作为在锥形虫细胞表面被溶菌抗体识别的拟糖 [5] (图 1). 药物和天然产物的糖基化修饰具有重要意义 [6][7] , 例如 3-硫代糖修饰的蛋白质可有效应用于细胞标记 [8][9] ; 胰高血糖素样态 1 (GLP-1)经过硫代糖的修饰后, 其生物活性和抗酶解性都得到了显著的提升 [10] ; 硫代糖类能用于治疗糖尿病 [11] 和调控植物细胞代谢 [12] . 此外, 硫代糖还作为合成低聚寡糖的重要中间体而被广泛研究 [13][14] . 许多已在市售或正在研发中的硫代糖类药物, 如金诺芬 (Auranfin) [15][16][17] 、芸苔葡糖硫苷(Glucosinolate) [18][19][20] 和吡利霉素(Pirlimycin) [21][22] 等(图 1)展现出了抗风湿炎症、抗癌特性及治疗神经系统疾病等效果.

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Palladium‐Catalyzed Stereospecific S‐Glycosylation by Allylic Substitution

Cited by 3 publications

References 58 publications

Highly Regio- and Diastereoselective Phosphine-Catalyzed [2 + 4] Annulation of Benzofuran-Derived Azadienes with Allyl Carbonates: Access to Spiro[benzofuran-cyclohexanes]

Highly Regio- and Diastereoselective Phosphine-Catalyzed [2 + 4] Annulation of Benzofuran-Derived Azadienes with Allyl Carbonates: Access to Spiro[benzofuran-cyclohexanes]

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

Regio- and Stereo-selective Synthesis of 1β-/3R-Aryl Thiosugar

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