16740-98-0Relevant articles and documents
Rhodium-Catalyzed Denitrogenative Transannulation of N-Sulfonyl-1,2,3-triazoles with Glycals Giving Pyrroline-Fused N-Glycosides
Bi, Jingjing,Tan, Qiang,Wu, Hao,Liu, Qingfeng,Zhang, Guisheng
supporting information, p. 6357 - 6361 (2021/08/23)
Described here is a selective synthesis of 2,3-dihydropyrrole-fused N-glycosides through rhodium-catalyzed denitrogenative transannulation of N-sulfonyl-1,2,3-triazoles with glycals. A series of pyrroline-fused N-glycosides are afforded in moderate to exc
Ir(I)-Catalyzed C?H Glycosylation for Synthesis of 2-Indolyl-C-Deoxyglycosides
Yu, Changyue,Liu, Yichu,Xie, Xiong,Hu, Shulei,Zhang, Shurui,Zeng, Mingjie,Zhang, Dan,Wang, Jiang,Liu, Hong
supporting information, p. 4926 - 4931 (2021/09/09)
The construction of 2-deoxy-C-glycosides has gradually become a hotspot of carbohydrate chemistry in recent years. In this work, we present an efficient, regioselective, stereoselective and widely applicable strategy for the synthesis of 2-indolyl-C-deoxyglycosides via Ir(I)-catalyzed, pyridine-group-directed C?H functionalization. This method exhibits high tolerance for the functional groups of indoles and the protecting groups of carbohydrates. Moreover, this protocol has good stereoselectivity and mainly produces β-configuration products. Gram-scale synthesis and several practical transformations were conducted for further applications. Meantime, we also explored the mechanism of this method and proposed a catalytic cycle. (Figure presented.).
Iron-Catalyzed Radical Cleavage/C?C Bond Formation of Acetal-Derived Alkylsilyl Peroxides
Shiozaki, Yoko,Sakurai, Shunya,Sakamoto, Ryu,Matsumoto, Akira,Maruoka, Keiji
supporting information, p. 573 - 576 (2020/02/20)
A novel radical-based approach for the iron-catalyzed selective cleavage of acetal-derived alkylsilyl peroxides, followed by the formation of a carbon–carbon bond is reported. The reaction proceeds under mild reaction conditions and exhibits a broad substrate scope with respect to the acetal moiety and the carbon electrophile. Mechanistic studies suggest that the present reaction proceeds through a free-radical process involving carbon radicals generated by the homolytic cleavage of a carbon–carbon bond within the acetal moiety. A synthetic application of this method to sugar-derived alkylsilyl peroxides is also described.
Method for preparing 3,4,6-tri-O-substituent-D-glucal
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Paragraph 0021; 0022; 0023, (2019/02/04)
The invention discloses a method for preparing 3,4,6-tri-O-substituent-D-glucal. The method comprises the following steps: (1) preparation of D-glucal: subjecting 3,4,6-tri-O-acetyl-D-glucal, which serves as a starting raw material, to a reaction under al
Carbonylative Negishi-Type Coupling of 2-Iodoglycals with Alkyl and Aryl Halides
Esteves, Henrique A.,Darbem, Mariana P.,Pimenta, Daniel C.,Stefani, Hélio A.
supporting information, p. 7384 - 7388 (2019/11/28)
C-Glycosides are valuable organic compounds in the field of medicinal chemistry due to their ubiquity inside living systems and pronounced biological activity. Herein, we describe an approach to alkyl-ketones bearing glycal units via the Pd-catalyzed carb
Palladium catalyzed stereocontrolled synthesis of C-aryl glycosides using glycals and arenediazonium salts at room temperature
Singh, Adesh Kumar,Kandasamy, Jeyakumar
supporting information, p. 5107 - 5112 (2018/07/29)
A stereocontrolled synthesis of aryl-C-glycosides was achieved using glycals and aryldiazonium salts in the presence of palladium acetate. A wide range of glycals including d-glucal, d-galactal, l-rhamnal, d-xylal and d-ribal underwent C-arylation at the anomeric carbon in the presence of different aryldiazonium tetrafluoroborates and gave synthetically useful 2,3-deoxy-3-keto-α-aryl-C-glycosides in good to excellent yields. Broad substrate scope, simple operation and room temperature reactions make this protocol very attractive in organic synthesis.
Effects of lipophilicity, protecting group and stereochemistry on the antimalarial activity of carbohydrate-derived thiochromans
Madumo, Gilbert K.,Moshapo, Paseka T.,Kinfe, Henok H.
, p. 817 - 833 (2018/01/10)
A series of novel carbohydrate-derived thiochromans has been successfully synthesized in order to investigate the influence of alkyl substituents on the aromatic ring of the thiophenol moiety in addition to the effect of protecting groups and stereochemistry on the sugar component of the target molecules. Results from the evaluation of the thiochromans for their antimalarial activity against the chloroquine-sensitive (3D7) strain of Plasmodium falciparum suggest that the presence of short chain alkyl substituents, a benzyl ether protecting group and equatorial orientation of the C-4 substituent on the sugar moiety are crucial structural features that impart high antimalarial activity.
Direct C-H Trifluoromethylation of Glycals by Photoredox Catalysis
Wang, Bang,Xiong, De-Cai,Ye, Xin-Shan
supporting information, p. 5698 - 5701 (2015/12/01)
A mild, efficient, and practical transformation for the direct C-H trifluoromethylation of glycals under visible light has been reported for the first time. This reaction employed fac-Ir3+(ppy)3 as the photocatalyst, Umemoto's reagent as the CF3 source, and a household blue LED or sunlight as the light source. Glycals bearing both electron-withdrawing and -donating protective groups performed this reaction smoothly. This visible light-mediated trifluoromethylation reaction was highlighted by the trifluoromethylation of the biologically important Neu2en moiety.
N-heterocyclic carbene catalyzed C-glycosylation: A concise approach from stetter reaction
Vedachalam, Seenuvasan,Tan, Shi Min,Teo, Hui Ping,Cai, Shuting,Liu, Xue-Wei
supporting information; experimental part, p. 174 - 177 (2012/02/16)
Described herein is the first example of an organocatalytic approach for acylanion addition to the anomeric carbon of 2-nitroglucal using an N-heterocyclic carbene catalyst. Control over the reaction conditions gives β-selective and nitro-eliminated C-glycosides, providing opportunities to produce new classes of C-glycoside.
α-Selective organocatalytic synthesis of 2-deoxygalactosides
Balmond, Edward I.,Coe, Diane M.,Galan, M. Carmen,McGarrigle, Eoghan M.
supporting information, p. 9152 - 9155 (2012/10/29)
Alpha rules: A thiourea acts as an efficient organocatalyst for the glycosylation of protected galactals to form oligosaccharides containing a 2-deoxymonosaccharide moiety (see scheme). The reaction is highly stereoselective for α-linkages and proceeds by way of a syn-addition mechanism. Copyright
