95015-48-8Relevant academic research and scientific papers
Experimental and theoretical study of the O3/O4 regioselectivity of glycosylation reactions of glucopyranosyl acceptors
Del Vigo, Enrique A.,Stortz, Carlos A.,Marino, Carla
, (2020/11/10)
The knowledge of the regioselectivity between different hydroxyl groups of glycosyl acceptors is valuable in planning simple strategies for the synthesis of oligosaccharides, minimizing the use of protecting groups. With the aim of obtaining deeper knowle
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
A novel O-fucosylation strategy preactivated by (p-Tol)2SO/Tf2O and its application for the synthesis of Lewis blood group antigen Lewisa
Li, Cui-yun,Liu, Guang-jian,Du, Wei,Zhang, Yuan,Xing, Guo-wen
supporting information, p. 2109 - 2112 (2017/05/09)
Based on a preactivation strategy using (p-Tol)2SO/Tf2O, a new O-fucosylation method with thioglycoside as donor under mild conditions was reported. High yields and excellent α-stereoselectivities of the fucosylation were obtained wi
A green and convenient method for regioselective mono and multiple benzoylation of diols and polyols
Zhang, Xiaoling,Ren, Bo,Ge, Jiantao,Pei, Zhichao,Dong, Hai
supporting information, p. 1005 - 1010 (2016/02/03)
An efficient method for regioselective benzoylation of diols and polyols was developed. The benzoylation is catalyzed by only 0.2 equiv of benzoate anion in acetonitrile with the addition of a stoichiometric amount of benzoic anhydride under very mild condition, leading to high yields. Compared with all other methods, this method shows particular advantage in regioselective multiple benzoylation of polyols, and in avoiding the use of any metal-based catalysts and any amine bases, which is more environment-friendly.
Halide promoted organotin-mediated carbohydrate benzylation: Mechanism and application
Zhou, Yixuan,Li, Jinyang,Zhan, Yingjie,Pei, Zhichao,Dong, Hai
, p. 2693 - 2700 (2013/03/28)
In the present study, the mechanistic origin of the promoted organotin-mediated carbohydrate benzylation by halides was explored by the comparison of the activation ability of halides on benzylation of methyl β-d-galactoside. It was demonstrated that the
Rapid assembly of gp120 oligosaccharide moieties via one-pot glycosidation-deprotection sequences
Pastore, Antonello,Adinolfi, Matteo,Iadonisi, Alfonso,Valerio, Silvia
experimental part, p. 1316 - 1323 (2010/10/02)
Mannosyl trihaloacetimidate donors equipped with a 2-O-Fmoc group can be effectively activated by catalytic Bi(OTf)3 in glycosidations. Despite the expected participating effect of the Fmoc group, the reaction solvent was found to be decisive f
Reductive openings of benzylidene acetals revisited: A mechanistic scheme for regio- and stereoselectivity
Johnsson, Richard,Ohlin, Markus,Ellervik, Ulf
supporting information; experimental part, p. 8003 - 8011 (2011/03/18)
Despite the importance of regioselective reductive openings of cyclic acetals, mechanistic details are scarce. In this study 4,6-O-benzylidene acetals were used as model compounds for deciphering the mechanism of regioselective openings using a variety of
FeCl3-catalysed cleavage of 1,2-butanediacetal protected diols
Tzschucke, C. Christoph,Pradidphol, Narathip,Diéguez-Vázquez, Alejandro,Kongkathip, Boonsong,Kongkathip, Ngampong,Ley, Steven V.
experimental part, p. 1293 - 1296 (2009/04/06)
Catalytic FeCl3 in acetic acid has been employed as a cost-effective, low-toxicity reagent for the removal of butane 1,2-diacetal protecting groups under mild conditions. Georg Thieme Verlag Stuttgart.
Direct preparation of diacetals from 1,2-diketones and their use as 1,2-diol protecting groups
Hense, Achim,Ley, Steven V.,Osborn, Helen M. I.,Owen, Dafydd R.,Poisson, Jean-Francois,Warriner, Stuart L.,Wesson, Kieron E.
, p. 2023 - 2031 (2007/10/03)
A range of 1,2-diketones have been evaluated as potential protecting groups for trans-1,2-diols via 1,2-diacetal formation. The procedure is especially useful in oligosaccharide and natural product synthesis.
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
