177696-56-9Relevant articles and documents
Additive-controlled synthesis of 1- and 2-dexoysugars from thioglycosides
Gao, Chen-Fei,Wu, Biao,Wu, Xia,Xiong, De-Cai,Ye, Xin-Shan
, (2021/12/29)
Two photoreactions for the synthesis of 1- and 2-deoxysugars from thioglycosides were developed. In the presence of Hantzsch ester as an additive, a wide range of 1-deoxysugars were synthesized in moderate to excellent yields under irradiation with UV light without an exogenous photosensitizer. On the other hand, the utilization of 2,4,6-tri-tert-butylpyrimidine (TTBP) as the additive furnished a variety of 2-deoxysugars as the main products from their corresponding thioglycosides. The reported methodology has a broad substrate scope and high functional group tolerance and is scalable to gram-scale reaction.
Gold-catalysed glycosylation reaction using an easily accessible leaving group
Koppolu, Srinivasa Rao,Niddana, Ramana,Balamurugan, Rengarajan
, p. 5094 - 5097 (2015/05/13)
Gold(iii)-catalysed glycosylation reaction has been developed by employing a new and easily accessible leaving group synthesized from ethyl cyanoacetate. Several nucleophiles like alcohols, thiols, allyltrimethylsilane, trimethylsilyl azide and triethylsilane have been reacted to make the corresponding glycosides in good yields and with marginal to excellent α-selectivity. This journal is
A biophysical study with carbohydrate derivatives explains the molecular basis of monosaccharide selectivity of the Pseudomonas aeruginosa lectin lecB
Sommer, Roman,Exner, Thomas E.,Titz, Alexer
, (2015/02/19)
The rise of resistances against antibiotics in bacteria is a major threat for public health and demands the development of novel antibacterial therapies. Infections with Pseudomonas aeruginosa are a severe problem for hospitalized patients and for patients suffering from cystic fibrosis. These bacteria can form biofilms and thereby increase their resistance towards antibiotics. The bacterial lectin LecB was shown to be necessary for biofilm formation and the inhibition with its carbohydrate ligands resulted in reduced amounts of biofilm. The natural ligands for LecB are glycosides of D-mannose and L-fucose, the latter displaying an unusual strong affinity. Interestingly, although mannosides are much weaker ligands for LecB, they do form an additional hydrogen bond with the protein in the crystal structure. To analyze the individual contributions of the methyl group in fucosides and the hydroxymethyl group in mannosides to the binding, we designed and synthesized derivatives of these saccharides.We report glycomimetic inhibitors that dissect the individual interactions of their saccharide precursors with LecB and give insight into the biophysics of binding by LecB. Furthermore, theoretical calculations supported by experimental thermodynamic data suggest a perturbed hydrogen bonding network for mannose derivatives as molecular basis for the selectivity of LecB for fucosides. Knowledge gained on the mode of interaction of LecB with its ligands at ambient conditions will be useful for future drug design.
Radical dimerization of glycosyl 2-pyridylsulfones with samarium (II) iodide in the presence of HMPA
Doisneau, Gilles,Beau, Jean-Marie
, p. 3477 - 3480 (2007/10/03)
Reduction of glycosyl 2-pyridylsulfones by samarium (II) iodide in the presence of HMPA leads to glycosyl dimers in up to 74% yield. This is rationalized by a free-radical mechanism.
A new strategy for the stereoselective syntheses of C-glycosyl compounds of β-pentapyranoses
Guo, Zhong-Wu,Hui, Yong-Zheng
, p. 2067 - 2073 (2007/10/03)
The C-glycosyl compounds of β-L-xylopyranose and β-D-arabinopyranose were conveniently prepared by reduction of methyl α-D-glucopyranoside and methyl α-D-mannopyranoside with triethylsilane in the presence of trimethylsilyl trifluoromethanesulfonate, respectively.
Samariumdiiodid-vermittelte Kupplung von Glycosylphosphaten mit Kohlenstoffradikal- oder -anion-Acceptoren - Synthese von C-Glycosiden
Hung, Shang-Cheng,Wong, Chi-Huey
, p. 2829 - 2832 (2007/10/03)
Keywords: C-Glycoside; Verknuepfungen; Samariumverbindungen; Synthesemethoden