53929-30-9Relevant 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
An Unexpected FeCl 3/C-Catalyzed β-Stereoselective Glycosylation in the Presence of the C(2)-Benzyl Group
Guo, Hong,Li, Juan,Si, Wenshuai,Tang, Jie,Tang, Tianjun,Wang, Zhongfu,Yang, Guofang,Zhang, Jianbo
, p. 2984 - 3000 (2019/07/22)
An efficient and completely β-stereoselective glycosylation that did not rely on neighboring group participation is described using 2-20 molpercent FeCl 3 /C as the catalyst and benzylated propargyl glycosides as the donors to reach yields up to 96percent under mild condition. With an octatomic-ring intermediate at the α-face of FeCl 3 /C with alkyne of propargyl glycosides, a panel of aglycones comprising aliphatic, alicyclic, unsaturated alcohols, halogenated alcohols, and phenols with different substitution were examined successfully for the exclusive β-stereoselective glycosylation reaction.
Simple and mild stereoselective O-glycosidation using 1,2-anhydrosugars under neutral conditions
Somasundaram, Devaraj,Balasubramanain, Kalpattu K.,Shanmugasundaram, Bhagavathy
supporting information, p. 764 - 767 (2019/02/16)
The ring opening of α-D-1,2-anhydrohexapyranoses with phenols proceeded smoothly in ethyl acetate (neutral conditions) in the absence of metal ion catalysts or additives to stereoselectively furnish 1,2-cis-α-aryl glycosides as the major product and 1,2-t
Ionic liquids as phase transfer catalysts: Enhancing the biphasic extractive epoxidation reaction for the selective synthesis of β-O-glycosides
Santiago, Cintia C.,Lafuente, Leticia,Bravo, Rodolfo,Díaz, Gisela,Ponzinibbio, Agustín
, p. 3739 - 3742 (2017/09/02)
Ionic liquids promoted the direct epoxidation of glycals acting as PTC. 1,2-anhydrosugars were prepared by the oxidation of glycals under biphasic conditions with dimethydioxirane generated in situ from oxone/acetone and amphiphilic IL's as catalysts. β-O
Glycosyl dithiocarbamates: β-selective couplings without auxiliary groups
Padungros, Panuwat,Alberch, Laura,Wei, Alexander
, p. 2611 - 2624 (2014/04/17)
In this article, we evaluate glycosyl dithiocarbamates (DTCs) with unprotected C2 hydroxyls as donors in β-linked oligosaccharide synthesis. We report a mild, one-pot conversion of glycals into β-glycosyl DTCs via DMDO oxidation with subsequent ring opening by DTC salts, which can be generated in situ from secondary amines and CS2. Glycosyl DTCs are readily activated with Cu(I) or Cu(II) triflate at low temperatures and are amenable to reiterative synthesis strategies, as demonstrated by the efficient construction of a tri-β-1,6-linked tetrasaccharide. Glycosyl DTC couplings are highly β-selective despite the absence of a preexisting C2 auxiliary group. We provide evidence that the directing effect is mediated by the C2 hydroxyl itself via the putative formation of a cis-fused bicyclic intermediate.
Access to new carbohydrate-functionalized polylactides via organocatalyzed ring-opening polymerization
Miao, Yong,Rousseau, Cyril,Mortreux, André,Martin, Patrick,Zinck, Philippe
, p. 5018 - 5026 (2012/06/29)
The 4-dimethylaminopyridine (DMAP) catalyzed ring-opening polymerization of lactide using various carbohydrate initiators has been assessed for the functionalization of polylactide. Selectively protected glucose derivatives bearing a free primary alcohol (Glc-1r) and a free secondary alcohol (Glc-2r), glucose and cyclodextrin diol derivatives (Glc-diol and CD-diol), methyl-α-d-glucopyranoside (Glc-Me) and native β-cyclodextrin (CD) were used as initiators. According to the solubility of the carbohydrate derivative, the polymerizations were conducted in chlorinated solvents and in the bulk. Relatively narrow distributions are obtained in high yields in the absence of side reactions, affording a 100% functionalization efficiency. The catalytic synthesis of new carbohydrate link-functionalized polylactides and carbohydrate core star polylactides is reported.
Silyl group migration in 1-O-silyl protected sugars-convenient synthesis of 2-O-unprotected sugars
Lassaletta, Jose M.,Meichle, Michaela,Weiler, Sven,Schmidt, Richard R.
, p. 241 - 254 (2007/10/03)
Reaction of 2-O-unprotected 1-9-silyl-protected D-glucose and D-galactose derivatives 5a-d with benzyl bromide in the presence of sodium hydride as the base afforded 1-O-benzyl 2-O-silyl derivatives 6aα/β - 6dα/β. Thus, prior to anomeric O-benzylation, t
The synthesis and characterization of 2-O-(6-O-L-glycero-α,β-D-manno-heptopyranosyl-α-D-glucopyranosyl)-α,β-D-glucopyranose
Nopogodev, Sergey A.,Pakulski, Zbigniew,Zamojski, Aleksander,Holst, Otto,Brade, Helmut
, p. 33 - 46 (2007/10/02)
The title compounds were synthesized, and appropriate derivatives were characterized by GLC, GLC-MS, and NMR spectroscopy.The GLC and GLC and GLC-MS data proved 2-O-(6-O-L-glycero-α-D-manno-heptopyranosyl-α-D-glucopyranosyl)-D-glucopyranose to be a consti
SYNTHESIS OF KOJITETRAOSE AND KOJIPENTAOSE
Takeo, Ken'Ichi,Suzuki, Yukiko
, p. 95 - 110 (2007/10/02)
Kojitriose 2)-α-D-Glcp-(1->2)-D-Glcp>, kojitetraose, and kojipentaose have been synthesised by silver perchlorate-promoted Koenigs-Knorr type condensation, using 3,4,6-tri-O-acetyl-2-O-allyl-β-D-glucopyranosyl chloride and hepta-O-acetyl-β-k
