353754-90-2Relevant academic research and scientific papers
A novel glycosidation promoted by the combination of trimethylsilyl halide and zinc triflate
Higashi,Susaki
, p. 2019 - 2022 (1992)
A novel glycosidation method has been developed which utilizes a trimethylsilyl halide-zinc triflate catalyst system to activate various benzyl-protected fucosyl, glucosyl and galactosyl esters. The promoter system was extended to use benzyl-protected alk
Synthesis of Unprecedented Sulfonylated Phosphono-exo-Glycals Designed as Inhibitors of the Three Mycobacterial Galactofuranose Processing Enzymes
Frédéric, Christophe J.-M.,Tikad, Abdellatif,Fu, Jian,Pan, Weidong,Zheng, Ruixiang B.,Koizumi, Akihiko,Xue, Xiaochao,Lowary, Todd L.,Vincent, Stéphane P.
supporting information, p. 15913 - 15920 (2016/10/25)
This study reports a new methodology to synthesize exo-glycals bearing both a sulfone and a phosphonate. This synthetic strategy provides a way to generate exo-glycals displaying two electron-withdrawing groups and was applied to eight different carbohydrates from the furanose and pyranose series. The Z/E configurations of these tetrasubstituted enol ethers could be ascertained using NMR spectroscopic techniques. Deprotection of an exo-glycal followed by an UMP (uridine monophosphate) coupling generated two new UDP (uridine diphosphate)-galactofuranose analogues. These two Z/E isomers were evaluated as inhibitors of UGM, GlfT1, and GlfT2, the three mycobacterial galactofuranose processing enzymes. Molecule 46-(E) is the first characterized inhibitor of GlfT1 reported to date and was also found to efficiently inhibit UGM in a reversible manner. Interestingly, GlfT2 showed a better affinity for the (Z) isomer. The three enzymes studied in the present work are not only interesting because, mechanistically, they are still the topic of intense investigations, but also because they constitute very important targets for the development of novel antimycobacterial agents.
Regioselective removal of the anomeric O-benzyl from differentially protected carbohydrates
Jalsa, Nigel Kevin
supporting information; scheme or table, p. 6587 - 6590 (2012/02/03)
A mild, regioselective deprotection of the anomeric O-benzyl from multi-functionally protected carbohydrates via catalytic transfer hydrogenation is described. The protocol is tolerant of O-benzyl and O-benzylidene protections at non-anomeric positions, g
Facile glycosylation strategy with two-stage activation of allyl glycosyl donors. Application to concise synthesis of Shigella flexneri serotype y O-antigen
Wang, Yun,Zhang, Xin,Wang, Pengfei
supporting information; experimental part, p. 4322 - 4328 (2010/11/18)
A practical, useful glycosylation method employing only allyl glycoside building blocks has been developed. The donor's glycosylation reactivity is turned on via isomerization of its anomeric allyl protecting group into the corresponding prop-1-enyl moiet
The use of a new magnesium-derived hydride reagent for carbohydrate derivatives
Szabovik,Medgyes,Antal,Varga,Knott,Liptak
, p. 1003 - 1009 (2007/10/03)
The magnesium hydride based reagent in THF solution is an excellent tool for the stereoselective reduction of different uloside derivatives. Sugar azides, sulfonyl esters give aminosugars and methylose derivatives without affecting other functionalities. Halogenated sugars or methylene derivatives are stable under these conditions. The reagent can be applied in the presence of a wide variety of blocking groups (acetals, benzyl and allyl ethers, imides, C=C bonds) generally used in the carbohydrate chemistry.
Building Units for Oligosaccharides, XXXIII. Synthesis of β-Glycosidically Linked Disaccharides of L-Rhamnose
Paulsen, Hans,Kutschker, Wolfram,Lockhoff, Oswald
, p. 3233 - 3241 (2007/10/02)
The 2,3,4-tri-O-benzyl-α-L-rhamnopyranosyl bromide (4) is a reactive halogenose which in the presence of a silver silicate catalyst reacts with saccharides containing a reactive hydroxyl group to give a β-glycosidically linked disaccharide with good selec
