493008-73-4Relevant academic research and scientific papers
A study of n-pentenylorthoesters having manno, gluco and galacto configurations in regioselective glycosylations
Jayaprakash,Fraser-Reid, Bert
, p. 490 - 498 (2007)
Kochetkov's extensive investigations of glycosyl orthoester and their analogs as glycosyl donors revealed that the alkyl derivatives were plagued by competition between the departing alcohol and the incoming acceptor. n-Pentenyl orthoesters (NPOEs) obviat
N-Heterocyclic silylene/germylene ligands in Au(i) catalysis
Parvin, Nasrina,Mishra, Bijoyananda,George, Anjana,Neralkar, Mahesh,Hossain, Jabed,Parameswaran, Pattiyil,Hotha, Srinivas,Khan, Shabana
supporting information, p. 7625 - 7628 (2020/08/25)
Cationic Au(i) complexes (2, 5 and 8) supported by N-heterocyclic carbene, silylene and germylene ligands were prepared and their potential as catalysts in glycosidation chemistry has been evaluated. Insights into the mechanism are provided using DFT studies. Practical application of them as catalysts was achieved by the synthesis of the branched pentamannan core of the HIV-gp120 envelope under mild conditions.
Nucleofuge Generating Glycosidations by the Remote Activation of Hydroxybenzotriazolyl Glycosides
Neralkar, Mahesh,Mishra, Bijoyananda,Hotha, Srinivas
, p. 11494 - 11504 (2017/11/10)
Hydroxybenzotriazole is routinely used in peptide chemistry for reducing racemization due to the increased reactivity. In this article, very stable hydroxybenzotriazolyl glucosides were identified to undergo glycosidation. The reaction was hypothesized to go through the remote activation by the Tf2O at the N3-site of HOBt followed by the extrusion of the oxocarbenium ion that was attacked by the glycosyl acceptor. Further, equilibration of the zwitterionic benzotriazolyl species makes the leaving group noncompetitive and generates the nucleofuge that has been reconverted to the glycosyl donor. The reaction is mild, high yielding, fast and suitable for donors containing both C2-ethers and C2-esters as well. The regenerative-donor glycosidation strategy is promising as it enables us to regenerate the glycosyl donor for further utilization. The utility of the methodology for the oligosaccharide synthesis was demonstrated by the successful synthesis of the branched pentamannan core of the HIV1-gp120 complex.
One pot/two donors/one diol give one differentiated trisaccharide: Powerful evidence for reciprocal donor-acceptor selectivity (RDAS)
Fraser-Reid, Bert,Lopez, J. Cristobal,Radhakrishnan,Nandakumar,Gomez, Ana M.,Uriel, Clara
, p. 2104 - 2105 (2007/10/03)
Three component, one-pot reactions involving equimolar amounts of the acceptor diol and both armed and disarmed donors presented simultaneously, produce a single double-differential glycosidation product; this phenomenon provides evidence for Reciprocal D
Synthesis of a nonasaccharide with two Lewis x trisaccharides anchored onto a branched trimannoside
Zhang,Brodzky,Sinay,Saint-Marcoux,Perly
, p. 1195 - 1216 (2007/10/02)
Double condensation of phenyl 3,4,6-tri-O-benzyl-2-O-[6-O-benzyl-2-deoxy-2-phthalimido-4-O-(2,3,4,6- tetra-O-benzoyl-β-D-galactopyranosyl)-3-O-(2,3,4-tri-O-benzyl-α-L-fu copyranosyl)-β-D-glucopyranosyl]-1-thio-α-D-mannopyranoside 31 with methyl 2,4-di-O-b
