56822-49-2Relevant academic research and scientific papers
Studies on carbohydrates IX highly stereoselective approach to 1-O-acyl-D-glucopyranose by using glucosyl trimethylsilyl ether as an intermediate
Cai,Li,Huang,Wang,Qiu
, p. 1735 - 1738 (1993)
Model reaction of α-D-glucopyranosyl trimethylsilyl ether 1 with a series of acids demonstrated that stereocontrolled glucosyl transfer with the retention of configuration at the anomeric center is best carried out in dichloromethane at room temperature w
Chemoselective and Diastereoselective Synthesis of C-Aryl Nucleoside Analogues by Nickel-Catalyzed Cross-Coupling of Furanosyl Acetates with Aryl Iodides
Li, Chao,Li, Luyang,Li, Yuxi,Shao, Feng,Tian, Xiaoying,Wang, Zheng
supporting information, (2021/11/30)
Canonical nucleosides are vulnerable to enzymatic and chemical degradation, yet their stable mimics—C-aryl nucleosides—have demonstrated potential utility in medicinal chemistry, chemical biology, and synthetic biology, although current synthetic methods remain limited in terms of scope and selectivity. Herein, we report a cross-electrophile coupling to prepare C-aryl nucleoside analogues from readily available furanosyl acetates and aryl iodides. This nickel-catalyzed modular approach is characterized by mild reaction conditions, broad substrate scope, excellent β-selectivity, and high functional-group compatibility. The exclusive chemoselectivity with respect to the aryl iodide enables efficient preparation of a variety of C-aryl halide furanosides suitable for various downstream transformations. The practicality of this transformation is demonstrated through the synthesis of a potent analogue of a naturally occurring NF-κB activator.
A general approach to C-Acyl glycosides via palladium/copper Co-catalyzed coupling reaction of glycosyl carbothioates and arylboronic acids
Wang, Li-Na,Niu, You-Hong,Cai, Qing-Hui,Li, Qin,Ye, Xin-Shan
, (2021/02/03)
A general and efficient approach to the synthesis of various C-acyl glycosides has been developed via Pd2(dba)3/CuTC co-catalyzed cross-coupling reaction of glycosyl carbothioates with arylboronic acids. The reaction showed a broad s
Establishment of Guidelines for the Control of Glycosylation Reactions and Intermediates by Quantitative Assessment of Reactivity
Chang, Chun-Wei,Wu, Chia-Hui,Lin, Mei-Huei,Liao, Pin-Hsuan,Chang, Chun-Chi,Chuang, Hsiao-Han,Lin, Su-Ching,Lam, Sarah,Verma, Ved Prakash,Hsu, Chao-Ping,Wang, Cheng-Chung
supporting information, p. 16775 - 16779 (2019/11/03)
Stereocontrolled chemical glycosylation remains a major challenge despite vast efforts reported over many decades and so far still mainly relies on trial and error. Now it is shown that the relative reactivity value (RRV) of thioglycosides is an indicator for revealing stereoselectivities according to four types of acceptors. Mechanistic studies show that the reaction is dominated by two distinct intermediates: glycosyl triflates and glycosyl halides from N-halosuccinimide (NXS)/TfOH. The formation of glycosyl halide is highly correlated with the production of α-glycoside. These findings enable glycosylation reactions to be foreseen by using RRVs as an α/β-selectivity indicator and guidelines and rules to be developed for stereocontrolled glycosylation.
IMPROVED PROCESS FOR PREPARATION OF 2,3,4,6-TETRA-O-BENZYL-D-GALACTOSE
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Page/Page column 25; 26; 27, (2020/01/08)
Provided herein is an improved process for the preparation of benzylated derivative of D-galactose, particularly 2,3,4,6-tetra-O-benzyl-D-galactose that gives higher yield and better purity being cost effective with reduced impurities.
Addition of Organozinc Reagents to Glycopyranosyl Cyanides: Access to Keto Ester-C-glycosides or Unsaturated Acyl-C-glycosides
Ella Obame, Idriss,Ireddy, Prathap,Guisot, Nicolas E. S.,Nourry, Arnaud,Saluzzo, Christine,Dujardin, Gilles,Dubreuil, Didier,Pipelier, Muriel,Guillarme, Stéphane
, p. 1735 - 1738 (2018/04/24)
Addition of Reformatsky-type or allylic zinc reagents to 2,3,4,6-tetra-O-benzylglycopyranosyl cyanides led to keto ester-C-glycosides or unsaturated acyl-C-glycosides in moderate to excellent yields in the galactose, glucose, and mannose series.
C-GLYCOSIDE COMPOUNDS USEFUL FOR TREATING DISEASE
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Paragraph 00190; 00191, (2017/10/06)
The present invention relates to mannoside derivative compounds useful as inhibitors of FimH and methods for the treatment or prevention of urinary tract infection.
MANNOSE-DERIVED ANTAGONISTS OF FIMH USEFUL FOR TREATING DISEASE
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Paragraph 0201, (2017/10/13)
The present invention relates to mannoside derivative compounds useful as inhibitors of FimH and methods for the treatment or prevention of urinary tract infection.
Chiral Catalyst-Directed Dynamic Kinetic Diastereoselective Acylation of Anomeric Hydroxyl Groups and a Controlled Reduction of the Glycosyl Ester Products
Wang, Hao-Yuan,Simmons, Christopher J.,Zhang, Yu,Smits, Angela M.,Balzer, Paul G.,Wang, Shuojin,Tang, Weiping
supporting information, p. 508 - 511 (2017/02/10)
A catalytic method is developed for the diastereoselective acylation of the anomeric hydroxyl group in diverse carbohydrates to form either α- or β-anomeric esters. While exclusive formation of the β-isomer was observed in most sugar substrates with one enantiomer of the chiral catalyst, moderate to high α-selectivity was obtained by using the other enantiomer of the chiral catalyst. The resulting α- and β-anomeric esters have very different reactivity toward a reduction reaction.
Improved preparation of 4(5)-aryl-2-(β-d-glucopyranosyl)-imidazoles, the most efficient glucose analogue inhibitors of glycogen phosphorylase
Szennyes, Eszter,Bokor, éva,Batta, Gyula,Docsa, Tibor,Gergely, Pál,Somsák, László
, p. 94787 - 94794 (2016/10/21)
The synthesis of 4(5)-aryl-2-(β-d-glucopyranosyl)-imidazoles, the currently most efficient glucose derived inhibitors of glycogen phosphorylase enzymes was amended and extended by using O-perbenzylated β-d-glucopyranosyl cyanide as the starting material.
