88087-63-2Relevant academic research and scientific papers
Regioselectivity of glycosylation reactions of galactose acceptors: An experimental and theoretical study
Del Vigo, Enrique A.,Stortz, Carlos A.,Marino, Carla
supporting information, p. 2982 - 2989 (2020/01/09)
Regioselective glycosylations allow planning simpler strategies for the synthesis of oligosaccharides, and thus reducing the need of using protecting groups. With the idea of gaining further understanding of such regioselectivity, we analyzed the relative
Boronic esters as protective groups in carbohydrate chemistry: processes for acylation, silylation and alkylation of glycoside-derived boronates
Mancini, Ross S.,Lee, Jessica B.,Taylor, Mark S.
, p. 132 - 143 (2016/12/27)
Procedures for selective installation of acyl, silyl ether and para-methoxybenzyl (PMB) ether groups to glycoside substrates have been developed, employing phenylboronic esters as protected intermediates. The sequence of boronic ester formation, functiona
A short and simple synthesis of branched mannooligosaccharides with [1-13C]-labelled terminal mannose units
Ivlev,Backinowsky,Abronina,Kononov,Kochetkov
, p. 275 - 286 (2007/10/03)
Mannosylation with 2,3,4,6-tetra-O-benzoyl-α-D-[1- 13C]mannopyranosyl bromide as a glycosyl donor has been used for the synthesis of 3,6-branched mannotri- and -pentaoside bearing labelled terminal mannopyranose units. Methyl 2,4-di-O-benzoyl-α
An easy access to a 3,6-branched mannopentaoside bearing one terminal [1-13C]-labeled D-mannopyranose residue1
Abronina,Backinowsky,Grachev,Sedinkin,Malysheva
, p. 1287 - 1293 (2007/10/03)
Methyl 2,4-di-O-benzoyl-α-D-mannopyranoside was used as a key intermediate in the synthesis of 3,6-branched mannopentaoside bearing one terminal D-[1-13C]mannopyranose residue, viz., methyl 6-O-[3,6-di-O-(α-D-mannopyranosyl)-α-D-mannopyranosyl)
Regioselective glycosylation of 3,6-unprotected mannoside derivatives: Fast access to high-mannose type oligosaccharides
Smiljanic, Nicolas,Halila, Sami,Moreau, Vincent,Djeda?ni-Pilard, Florence
, p. 8999 - 9002 (2007/10/03)
A regioselective glycosylation of 3,6-unprotected mannoside acceptors was investigated. With glycosyl trichloroacetimidate donors, when an excess of trimethylsilyl trifluoromethanesulfonate is used as the catalyst, 6-O-glycosylation exclusively occurred affording a silylated disaccharide that could be involved in a subsequent glycosylation reaction. As an illustration, the fast synthesis of two trisaccharides and one pentasaccharide was achieved.
Regioselective benzoylation of sugars mediated by excessive Bu2SnO: Observation of temperature promoted migration
Zhang, Zhiyuan,Wong, Chi-Huey
, p. 6513 - 6519 (2007/10/03)
Regioselective benzoylation of carbohydrates using an excess of dibutyltin oxide (Bu2SnO) at increased reaction temperatures has been developed for the synthesis of several glycoside benzoates with one or two free hydroxyl groups, including gal
Synthesis of a tri- and a tetradeoxy analogue of methyl 3,6-di-O-α-D-mannopyranosyl-α-D-mannopyranoside for investigation of the binding site of various plant lectins
Oscarson, Stefan,Svahnberg, Par
, p. 207 - 212 (2007/10/03)
The synthesis of the 2,4,3'-trideoxy and 2,4,3',4'-tetradeoxy analogues of the trimannoside part of the core structure of N-linked glycoproteins, methyl 3,6-di-O-α-D-mannopyranosyl-α-D-mannopyranoside, is described. A 2,4-dideoxy (1→6)-linked disaccharide
Preparation, structure, derivatisation and NMR data of cyclohexane-1,2-diacetal protected carbohydrates
Grice, Peter,Ley, Steven V.,Pietruszka, Joerg,Priepke, Henning W. M.,Warriner, Stuart L.
, p. 351 - 363 (2007/10/03)
Acid catalysed reaction of monosaccharides with 1,1,2,2-tetramethoxycyclohexane results in selective protection of vicinal, diequatorial, diol functionality as a cyclohexane-1,2-diacetal (CDA). This new methodology complements classical cyclic acetal prot
Regioselective Monoacylation of Some Glycopyranosides via Cyclic Tin Intermediates
Tsuda, Yoshisuke,Haque, Md. Ekramul,Yoshimoto, Kimihiro
, p. 1612 - 1624 (2007/10/02)
Selective mono-benzoylation of some pento- and hexo-pyranosides (Me β-L-Ara, Ph α-L-Ara, Me α-D-Xyl, Me β-D-Xyl, Me α-D-Glc, Me-β-D-Glc, Me α-D-Gal, Me β-D-Gal, and Me α-D-Man) by using Bu2SnO was examined in comparaison with the results of the (Bu3Sn)2O method and direct benzoylation.The Bu2SnO method is particularly useful in that it selectively activates an equatorial hydroxyl group wich bears an oxygenated function (OH or OMe) in a cis relationship at an adjacent position, even in the presence of a more reactive primary OH group.The various mono- and di-O-benzoyl derivatives prepared in this work were unambiguously identified by analysis of their 13C-nuclear magnetic resonance spectra.
