51755-03-4Relevant academic research and scientific papers
A Chiral Copper Catalyzed Site-Selective O-Alkylation of Carbohydrates
Ren, Bo,Wang, Jiaxi,Zhang, Mengyao,Chen, Yue,Zhao, Wei
supporting information, p. 665 - 670 (2021/12/02)
Highly regioselective alkylation of sugar hydroxyl groups has always been an important challenge in carbohydrate chemistry, especially for the selective alkylation of trans diols, there is no direct and efficient catalytic method so far. A chiral copper c
Catalytic Site-Selective Acylation of Carbohydrates Directed by Cation-n Interaction
Xiao, Guozhi,Cintron-Rosado, Gabriel A.,Glazier, Daniel A.,Xi, Bao-Min,Liu, Can,Liu, Peng,Tang, Weiping
supporting information, p. 4346 - 4349 (2017/04/04)
Site-selective functionalization of hydroxyl groups in carbohydrates is one of the long-standing challenges in chemistry. Using a pair of chiral catalysts, we now can differentiate the most prevalent trans-1,2-diols in pyranoses systematically and predictably. Density functional theory (DFT) calculations indicate that the key determining factor for the selectivity is the presence or absence of a cation-n interaction between the cation in the acylated catalyst and an appropriate lone pair in the substrate. DFT calculations also provided a predictive model for site-selectivity and this model is validated by various substrates.
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 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
