194088-19-2Relevant academic research and scientific papers
Exploring the Biochemical Foundations of a Successful GLUT1-Targeting Strategy to BNCT: Chemical Synthesis and in Vitro Evaluation of the Entire Positional Isomer Library of ortho-Carboranylmethyl-Bearing Glucoconjugates
Matovi?, Jelena,J?rvinen, Juulia,Sokka, Iris K.,Imlimthan, Surachet,Raitanen, Jan-Erik,Montaser, Ahmed,Maaheimo, Hannu,Huttunen, Kristiina M.,Per?niemi, Sirpa,Airaksinen, Anu J.,Sarparanta, Mirkka,Johansson, Mikael P.,Rautio, Jarkko,Ekholm, Filip S.
, p. 285 - 304 (2020/12/21)
Boron neutron capture therapy (BNCT) is a noninvasive binary therapeutic modality applicable to the treatment of cancers. While BNCT offers a tumor-targeting selectivity that is difficult to match by other means, the last obstacles preventing the full har
New class of alkynyl glycoside analogues as tyrosinase inhibitors
Saehlim, Natthiya,Athipornchai, Anan,Sirion, Uthaiwan,Saeeng, Rungnapha
, (2020/06/01)
A new series of alkynyl glycoside analogues were designed and synthesized from cheap and a commercially available sugar by introduction of various alkynyl and alkyl groups at C-1 and C-6 positions of the sugar ring. The inhibitory abilities of alkynyl gly
Visible Light Enables Aerobic Iodine Catalyzed Glycosylation
Krumb, Matthias,Lucas, Tobias,Opatz, Till
, p. 4517 - 4521 (2019/08/06)
A versatile protocol for light induced catalytic activation of thioglycosides using iodine as an inexpensive and readily available photocatalyst was developed. Oxygen serves as a green and cost-efficient terminal oxidant and irradiation is performed with a common household LED-bulb. The scope of this glycosylation protocol was investigated in the synthesis of O-glycosides with yields up to 95 %.
Tris(pentafluorophenyl)borane-promoted stereoselective glycosylation with glycosyl trichloroacetimidates under mild conditions
Mishra, Kunj Bihari,Singh, Adesh Kumar,Kandasamy, Jeyakumar
, p. 4204 - 4212 (2018/04/14)
Tris(pentafluorophenyl)borane-promoted stereoselective glycosylation with trichloroacetimidate glycosyl donors is described. The reactions proceed efficiently with a wide range of acceptors, from sugar to nonsugar, under mild conditions in the presence of
Click Inspired Synthesis of 1,2,3-Triazole-linked 1,3,4-Oxadiazole Glycoconjugates
Kushwaha, Divya,Tiwari, Vinod K.
, p. 2454 - 2462 (2017/07/25)
The glycoconjugation of biologically privileged 1,3,4-oxadiazole scaffold is described via Cu(I)-catalyzed azide–alkyne cycloaddition. A series of glycosyl alkynes 1b–i, obtained from various commercial sugars, were treated with azide functionalized 1,3,4-oxadiazole using click chemistry to access triazole-linked glycosylated 1,3,4-oxadiazoles 10b–i in good yields. The structure of the developed glycoconjugates has been ascertained by extensive spectroscopic analysis (1H &13C NMR, IR, and MS).
Polyvinyl trisulfonate ethylamine based solid acid catalyst for the efficient glycosylation of sugars under solvent free conditions
Chaugule, Avinash A.,Jadhav, Amol R.,Kim, Hern
, p. 104715 - 104724 (2015/12/30)
Heterogeneous Bronsted solid acid catalysts have the potential to decrease the environmental impact related to chemical production. Herein, we have synthesized polyvinyl bound trisulfonate ethylamine chloride (PV-THEAC) and polyvinyl bound disulfonate ethylamine (PV-DSEA) as Bronsted solid acid catalysts which exhibited effective catalytic activity for acid catalyzed glycosylation reactions with sugar derivatives. In particular, 0.3 equiv. of the PV-THEAC catalyst was found to be the most efficient and a reusable catalyst for glycosylation reactions. A high density of the trisulfonic group (-OSO3H) contributed to the excellent catalytic activity during glycosylation. Moreover, glycosylation reactions with d-mannose, d-xylose and d-glucose have been studied with alcohol. Remarkable acceleration of the glycosylation reaction using a glycosyltrichloroacetimidate donor was obtained with the selective production of β-glycoside.
Gold-catalyzed reactions of 2-c-branched carbohydrates: Mild glycosidations and selective anomerizations
Vidadala, Srinivasa Rao,Pimpalpalle, Tukaram M.,Linker, Torsten,Hotha, Srinivas
supporting information; experimental part, p. 2426 - 2430 (2011/06/10)
2-C-branched methyl glycosides react with various alcohols under gold catalysis to transglycosylated products. The method is applicable for the convenient synthesis of disaccharides. Without nucleophile a selective anomerization occurs, giving first acces
Gold mediated glycosylations: Selective activation of propargyl 1,2-orthoesters in the presence of aglycones containing a propargyl moiety
Sureshkumar, Gopalsamy,Hotha, Srinivas
supporting information; experimental part, p. 4282 - 4284 (2009/03/12)
Selective activation of propargyl 1,2-orthoesters in the presence of propargyl glycosides and propargyl ethers was studied; a catalytic amount of AuBr3 activated the propargyloxy group of the 1,2-orthoester thereby giving access to disaccharide
Propargyl glycosides as stable glycosyl donors: Anomeric activation and glycoside syntheses
Hotha, Srinivas,Kashyap, Sudhir
, p. 9620 - 9621 (2007/10/03)
The advantages of stable glycosyl donors for saccharide coupling are many, and we describe herein the utility of propargyl glycosides for anomeric activation and glycoside synthesis exploiting the alkynophilicity of AuCl3. Various aglycones wer
