503303-06-8Relevant academic research and scientific papers
One-pot synthesis of orthogonally protected sugars through sequential base-promoted/acid-catalyzed steps: A solvent-free approach with self-generation of a catalytic species
Traboni, Serena,Bedini, Emiliano,Giordano, Maddalena,Iadonisi, Alfonso
supporting information, p. 1777 - 1780 (2019/06/07)
A varied set of solvent-free, one-pot synthetic sequences were developed to carry out the orthogonal protection of saccharide polyols. These sequences are composed of an initial regioselective benzylation, silylation or iodination (under mildly basic cond
Stereocontrolled Synthesis of Phenolic α-d-Glycopyranosides
St-Pierre, Gabrielle,Dafik, Laila,Klegraf, Ellen,Hanessian, Stephen
, p. 3575 - 3588 (2016/10/17)
Adopting the ‘remote activation concept’ toward stereocontrolled glycoside synthesis with minimal use of protection groups, a general synthesis of phenolic 1,2-cis glycopyranosides is reported, as exemplified by aryl α-d-galacto-, α-d-gluco- and 2-azido α-d-glucopyranosides among others using glycosyl donors bearing an anomeric (3-bromo-2-pyridyloxy) group and catalyzed by methyl triflate.
Solution and Solid-Phase Stereocontrolled Synthesis of 1,2-cis-Glycopyranosides with Minimally Protected Glycopyranosyl Donors Catalyzed by BF3-N,N-Dimethylformamide Complex
St-Pierre, Gabrielle,Hanessian, Stephen
supporting information, p. 3106 - 3109 (2016/07/14)
Methods are described for the stereoselective synthesis of 1,2-cis glycopyranosides in the d-galacto, d-gluco, and 2-azido-2-deoxy-d-glucopyranoside series utilizing minimally protected (3-bromo-2-pyridyloxy) β-d-glycopyranosyl donors in the presence of BF3-N,N-dimethylformamide (DMF) as a catalyst and a variety of alcohol acceptors relying on the "remote activation concept". Precursors to antifreeze glycopeptide components are synthesized in excellent yields and high α/β ratios. The method is adaptable to one-pot sequential glycosidation as well as to solid-supported synthesis giving access to diverse sets of minimally protected α-d-glycopyranosides as major products.
Concise synthesis of a pentasaccharide related to the anti-leishmanial triterpenoid saponin isolated from Maesa balansae
Rajput, Vishal Kumar,Mukhopadhyay, Balaram
, p. 6924 - 6927 (2008/12/22)
(Chemical Equation Presented) Concise synthesis of the glycone part (a pentasaccharide) of the anti-leishmanial triterpenoid saponin isolated from Maesa balansae is reported. A late-stage TEMPO-mediated oxidation of a primary hydroxyl group to carboxylic
Aflexible synthesis of cyclopentitol derivatives based on ring-closing metathesis of carbohydrate-derived 1,6-dienes
Ovaa, Huib,Lastdrager, Bas,Codee, Jeroen D. C.,Van der Marel, Gijs A.,Overkleeft, Herman S.,Van Boom, Jacques H.
, p. 2370 - 2377 (2007/10/03)
Four partially protected stereoisomeric cyclopentenetriols 5, 10, 15 and 21 have been prepared by ring-closing metathesis of carbohydrate-derived 1,6-dienes. The presence of a differentiated allylic alcohol in the cyclopentenetriols allows a variety of synthetic transformations, underlining the synthetic use of the prepared cyclopentenetriol derivatives as chiral building blocks.
A versatile approach to the synthesis of highly functionalised carbocycles
Ovaa, Huib,Codee, Jeroen D. C.,Lastdrager, Bas,Overkleeft, Herman S.,Van Der Marel, Gijs A.,Van Boom, Jacques H.
, p. 5063 - 5066 (2007/10/03)
A synthetic route towards conduramine and carbasugar derivatives based on the transformation (i.e. two-carbon Wittig olefination and ester reduction) of the Vasella rearrangement product derived from D-galactose followed by either a [3,3] Overman or a [2,3]-Wittig-Still sigmatropic rearrangement, and subsequent ring-closing metathesis, is presented.
