58341-66-5Relevant articles and documents
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
, 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
, 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.
Tin-mediated regioselective benzylation and allylation of polyols: Applicability of a catalytic approach under solvent-free conditions
Giordano, Maddalena,Iadonisi, Alfonso
, p. 213 - 222 (2014/01/17)
The first catalytic version of the stannylene-mediated benzylation and allylation of polyols is reported. The methodology is based on a simple solvent-free protocol that significantly advances, in terms of both experimental ease and synthetic scope, the a
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
A tin-free regioselective radical de-o-benzylation by an intramolecular hydrogen atom transfer on carbohydrate templates
Attouche, Angie,Urban, Dominique,Beau, Jean-Marie
, p. 9572 - 9575 (2013/09/23)
Radically selective: A remarkable 1,7-hydrogen atom transfer of a benzylic hydrogen atom to an O-silylmethylene radical initiates a regioselective de-O-benzylation of benzylated saccharides. The reaction terminates by an ionic mechanism and is general for hydroxy benzylated substrates having a variety of functional groups. Copyright
Synthesis and glycosidase inhibitory profiles of functionalised morpholines and oxazepanes
Burland, Peter A.,Osborn, Helen M.I.,Turkson, Andrea
experimental part, p. 5679 - 5692 (2011/10/31)
In this work libraries of morpholines and oxazepanes have been prepared via the reductive amination reaction between dialdehydes, derived from carbohydrates, and a range of amines. In this way, functionalised morpholines and oxazepanes have been prepared
Some observations on the reductive ring opening of 4,6-O-benzylidene acetals of hexopyranosides with the borane trimethylamine-aluminium chloride reagent
Daragics, Katalin,Szabó, Pál,Fügedi, Péter
experimental part, p. 1633 - 1637 (2011/09/14)
Reductive ring openings of 3-O-benzoyl-4,6-O-benzylidene-d-glucopyranosides with BH3·NMe3-AlCl3 are accompanied by side reactions, such as debenzoylation and reduction of the benzoate to benzyl ether. This phenomenon was r
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