100662-89-3Relevant academic research and scientific papers
Benzoxaborole Catalyst for Site-Selective Modification of Polyols
Kusano, Shuhei,Miyamoto, Shoto,Matsuoka, Aki,Yamada, Yuji,Ishikawa, Ryuta,Hayashida, Osamu
supporting information, p. 1598 - 1602 (2020/02/11)
The site-selective modification of polyols bearing several hydroxyl groups without the use of protecting groups remains a significant challenge in synthetic chemistry. To address this problem, novel benzoxaborole derivatives were designed as efficient catalysts for the highly site-selective and protecting-group-free modification of polyols. To identify the effective substituent groups enhancing the catalytic activity and selectivity, a series of benzoxaborole catalysts 1a–k were synthesized. In-depth analysis for the substituent effect revealed that 1i–k, bearing multiple electron-withdrawing fluoro- and trifluoromethyl groups, exhibited the greatest catalytic activity and selectivity. Moreover, 1i-catalyzed benzoylation, tosylation, benzylation, and glycosylation of various cis-1,2-diol derivatives proceeded with good yield and site-selective manner.
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
Regioselective alkylation of carbohydrate derivatives catalyzed by a diarylborinic acid derivative
Chan, Lina,Taylor, Mark S.
supporting information; experimental part, p. 3090 - 3093 (2011/08/03)
Regioselective, catalyst-controlled monoalkylations of cis-vicinal diol motifs in carbohydrate derivatives, using a diphenylborinic ester precatalyst, are described. Selective installation of benzyl, naphthylmethyl, 4-bromobenzyl and benzyloxymethyl protective groups at a single secondary hydroxy group of ten representative carbohydrate derivatives illustrates the scope of this method. This new mode of catalytic reactivity represents an operationally simple method to access useful monoalkylated building blocks while avoiding the use of stoichiometric quantities of organotin reagents.
Regioselective Monoalkylation of Non-protected Glycopyranosides by the Dibutyltin Oxide Method
Haque, Mohammed Ekramul,Kikuchi, Tohru,Yoshimoto, Kimihiro,Tsuda, Yoshisuke
, p. 2243 - 2255 (2007/10/02)
Regioselective monoalkylation of some pento- and hexopyranosides (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) was examined by using the dibutyltin oxide method without protecting the hydroxyl groups.By this method, alkylation proceeds more or less in the same fashion as reported for acylation (through the formation of cyclic tin intermediates) and selectively activates an equatorial hydroxyl group which has an oxygenated function (OH or OMe) in a cis relationship at an adjacent position, even in the presence of a more reactive primary hydroxyl group.However, in some instances the position of activation is different.Various monoalkyl ethers thus prepared were identified by analyses of their carbon-13 nuclear magnetic resonance spectra.Keywords-regioselective monoalkylation; glycopyranoside; dibutyltin oxide; cis-vicinal glycol; benzylation; allylation; methoxymethylation; methylation;13C-NMR
