162061-34-9Relevant articles and documents
Anodic Reactivity of Alkyl S-Glucosides
Deore, Bhavesh,Ocando, Joseph E.,Pham, Lan D.,Sanhueza, Carlos A.
, p. 5952 - 5960 (2022/04/28)
A voltammetric study of a series of alkyl and aryl S-glucosides unveiled the reactivity patterns of alkyl S-glucosides toward anodic oxidation and found noteworthy differences with the trends followed by aryl derivatives. The oxidation potential of alkyl S-glucosides, estimated herein from square-wave voltammetry peak potentials (Ep), depends on the steric properties of the aglycone. Glucosides substituted with bulky groups exhibit Ep values at voltages more positive than the values of those carrying small aglycones. This relationship, observed in all analyzed alkyl series, is evidenced by good linear correlations between Ep and Taft's steric parameters (ES) of the respective alkyl substituents. Moreover, the role of the aglycone's steric properties as a primary reactivity modulator is backed by poor correlations between Ep and the radical stabilization energies (RSEs) of the aglycone-derived thiyl radicals (RS?). In contrast, aryl glucosides' Ep values exhibit excellent correlations with the aryl substituents' Hammett parameters (σ+) and the ArS?RSEs, evidencing the inherent stability of the reactive radical intermediate as the primary factor controlling aryl glucoside's electrochemical reactivity. The reactivity differences between alkyl and aryl S-glucosides also extend to the protective group's effect on Ep. Alkyl S-glucosides' reactivity proved to be more sensitive to protective group exchange.
Effects of frozen conditions on stereoselectivity and velocity of O-glycosylation reactions
Ishiwata, Akihiro,Sakurai, Ayaka,Dürr, Katharina,Ito, Yukishige
experimental part, p. 3687 - 3695 (2010/08/03)
Rate acceleration of O-glycosylation had been observed in p-xylene under frozen conditions, when thioglycosides were activated by methyl trifluoromethane sulfonate. Curiously, significant perturbation of stereoselectivity was observed. Effects of various
The Glc2Man2-fragment of the N-glycan precursor - A novel ligand for the glycan-binding protein malectin?
Mueller, Lisa N.,Muhle-Goll, Claudia,Biskup, Moritz B.
supporting information; experimental part, p. 3294 - 3299 (2010/08/21)
The Glcα(1→3)Glcα(1→3)Manα(1→2)Man tetrasaccharide (Glc2Man2-fragment), a substructure of the natural N-glycan precursor, was synthesized. The interaction of this fragment with the protein malectin, a carbohydrate binding protein localized in the endoplasmatic reticulum, was investigated by 1H15N HSQC experiments and isothermal calorimetry. The chemical shift perturbations of nuclei in the protein's backbone caused by the binding of the Glc 2Man2-fragment to malectin suggest a binding mode like the known ligand nigerose. The Royal Society of Chemistry 2010.
Confirmation of the structure of a glucono-1,4-lactone derivative obtained from silylation of glucono-1,5-lactone
Murphy, Paul V.,McDonnell, Ciaran,Haemig, Ludger,Paterson, Duncan E.,Taylor, Richard J. K.
, p. 79 - 85 (2007/10/03)
Silylation reactions of glucono-1,5-lactone can give the persilylated glucono-1,5-lactone or the persilylated 1,4-lactone depending on the reaction conditions employed. The structure of 2,3,5,6-tetra-O-(tert-butyldimethylsilyl)-D-glucono-1,4-lactone, obta
A new route to exo-glycals using the Ramberg-Baecklund rearrangement
Griffin, Frank K.,Paterson, Duncan E.,Murphy, Paul V.,Taylor, Richard J. K.
, p. 1305 - 1322 (2007/10/03)
A new route to exo-glycals 4 is described in which glycosyl sulfones 3 are subjected to the Meyers variant of the Ramberg-Baecklund rearrangement. The conversion of sulfones derived from glucose, galactose, mannose, cellobiose, and ribose into di-, tri-, and tetra-substituted alkenes is reported. Preliminary mechanistic studies of this process are also described. Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002.
Rearrangement of 1-O-(thio-p-nitrobenzoyl)thiocarbonyl galactoside: A novel access to α-thioglycoside derivatives
Josse, Solen,Le Gal, Julien,Pipelier, Muriel,Cléophax, Jeannine,Olesker, Alain,Pradère, Jean-Paul,Dubreuil, Didier
, p. 237 - 239 (2007/10/03)
The synthesis of galactosides thiolate and thioester is described by direct S-glycosylation process from 1-O-(thio-p-nitrobenzoyl)thiocarbonyl galactoside. Three novel anomeric groups are presented as potent glycoside activators: O-(thio-p-nitrobenzoyl)th
Observations on the activation of methyl thioglycosides by iodine and its interhalogen compounds
Kartha, K.P. Ravindranathan,Cura, Peter,Aloui, Mahmoud,Readman, S. Kristy,Rutherford, Trevor J.,Field, Robert A.
, p. 581 - 593 (2007/10/03)
Treatment of 'armed' methyl thiogalactosides with iodine in the absence of an acceptor alcohol results in thioglycoside epimerisation, whereas there is no effect on the corresponding 'disarmed' methyl thioglycosides. In contrast, iodine-hexamethyldisilane (which generates iodotrimethylsilane in situ) brings about epimerisation of 'disarmed' thioglycosides, ultimately giving rise to the corresponding α-glycosyl iodides on extended exposure. Cross-over experiments show the former iodine-promoted epimerisation process to be intermolecular, whereas the latter iodine-hexamethyldisilane-promoted epimerisation is intramolecular. Treatment of the same methyl thiogalactosides with iodine monobromide gives rise to the thermodynamically favoured α-glycosyl bromides, whereas reaction with iodine monochloride initially gives the kinetic β-glycosyl chlorides, which slowly epimerise to the thermodynamic α-linked products. Differences in the outcome of thioglycoside activation by I-I, I-Br and I-Cl suggest there may be scope for influencing the stereochemical course of thioglycoside-based glycosylation reactions through careful choice of promoter. Copyright (C) 2000 Elsevier Science Ltd.
A Ramberg-Backlund approach to exo-glycals
Griffin, Frank K.,Murphy, Paul V.,Paterson, Duncan E.,Taylor, Richard J.K.
, p. 8179 - 8182 (2007/10/03)
A new route to exo-glycals is described which starts from S-glycoside dioxides and utilises Meyers' variant of the Ramberg-Backlund rearrangement. The methodology is successful with glucose, galactose, mannose, xylose, fucose and ribose derivatives, and has been used to prepare di-, tri- and tetra-substituted alkenes.
Synthesis and two-dimensional nuclear magnetic resonance analysis of a tetra- and a hexa-saccharide fragment of the O-specific polysaccharide of Shigella dysenteriae type 1
Pozsgay, Vince,Coxon, Bruce
, p. 189 - 216 (2007/10/02)
The synthesis of the tetra- and hexa-succharide methyl glycosides α-D-Galp-(1-->3)-α-D-GlcpNAc-(1-->3)-α-L-Rhap-(1-->3)-α-L-Rhap-OMe (1), and α-L-Rhap-(1-->3)-α-L-Rhap-(1-->2)-α-D-Galp-(1-->3)-α-D-GlcpNAc-(1-->3)-α-L-Rhap-(1-->3)-α-L-Rhap-OMe (3) is descr
Activation and synthetic applications of thiostannanes. A new method for synthesis of thio- and selenoglycosides
Sato, Tsuneo,Fujita, Yukihiro,Otera, Junzo,Nozaki, Hitosi
, p. 239 - 242 (2007/10/02)
Exposure of thiostannane to acetyl or methyl glycosides in the presence of a catalytic amount of Bu2Sn(OTf)2 provides thioglycosides in good yields. Selenoglycosidation is achieved in a like manner by use of selenostannane.
