119237-86-4Relevant academic research and scientific papers
Synthesis of the mannopeptimycin disaccharide and its conjugation with 4-alkylidene-β-lactams
Adinolfi, Matteo,Giacomini, Daria,Iadonisi, Alfonso,Quintavalla, Arianna,Valerio, Silvia
experimental part, p. 2895 - 2899 (2009/04/06)
The disaccharide moiety of the antibiotic mannopeptimycin has been synthesized as a (N-phenyl)trifluoroacetimidate donor, the reactivity of which was tested in conjugation with a 4-alkylidene-β-lactam acceptor. Key steps of the synthesis were Bi(OTf)
Synthesis of 1-deoxyhept-2-ulosyl-glycono-1,5-lactone utilizing α-selective O-glycosidation of 2,6-anhydro-1-deoxy-d-hept-1-enitols
Namme, Rie,Mitsugi, Takashi,Takahashi, Hideyo,Shiro, Moto,Ikegami, Shiro
, p. 9183 - 9192 (2007/10/03)
A series of 1-deoxy-heptulo-2-pyranosyl-glycono-1,5-lactones were synthesized utilizing completely α-selective O-glycosidation of heptenitols. Anomeric configuration of the products was confirmed by 3JC,H coupling measurement and X-ray crystal structural analysis. The benzyl-protected ketosyl saccharides were partly unstable, and glycosidic linkage was prone to cleave under the usual debenzylation conditions. To prevent this, we surveyed various additives for the Pd-catalyzed hydrogenation reaction and found that basic alumina was the most effective.
Efficient installation of β-mannosides using a dehydrative coupling strategy
Codee, Jeroen D. C.,Hossain, Laila H.,Seeberger, Peter H.
, p. 3251 - 3254 (2007/10/03)
(Chemical Equation Presented) A new coupling procedure for the construction of the challenging β-mannosidic bond is described. Dehydrative mannosylation using 4,6-O-benzylidene mannopyranoses allows for the formation of β-mannosides in excellent yield. Th
Synthesis of a novel dioxan sialic acid analog
Perron-Sierra, Fran?oise M.,Burbridge, Mike,Péan, Christophe,Tucker, Gordon C.,Casara, Patrick
, p. 4163 - 4166 (2007/10/03)
A preparative scale synthesis of a dioxan sialic acid analog was achieved from D-mannose. The conformation and the acidic character of this dioxan derivative, closely related to sialic acid, provides a scaffold for drug design.
Stereochemical Control in Hex-5-enyl Radical Cyclizations: From Carbohydrates to Carbocycles. 3
RajanBabu, T. V.,Fukunaga, Tadamichi,Reddy, G. S.
, p. 1759 - 1769 (2007/10/02)
The hex-5-enyl radical cyclization reaction was applied to prepare highly oxygenated cyclopentanoids from aldopyranose sugars.The Wittig reaction of the sugars readily provides hex-5-en-1-ols which were converted to hex-5-enyl radicals via one of the vari
