201056-61-3Relevant academic research and scientific papers
Studies of Catalyst-Controlled Regioselective Acetalization and Its Application to Single-Pot Synthesis of Differentially Protected Saccharides
Wang, Sibin,Zhelavskyi, Oleksii,Lee, Jeonghyo,Argüelles, Alonso J.,Khomutnyk, Yaroslav Ya.,Mensah, Enoch,Guo, Hao,Hourani, Rami,Zimmerman, Paul M.,Nagorny, Pavel
, p. 18592 - 18604 (2021/11/16)
This article describes studies on the regioselective acetal protection of monosaccharide-based diols using chiral phosphoric acids (CPAs) and their immobilized polymeric variants, (R)-Ad-TRIP-PS and (S)-SPINOL-PS, as the catalysts. These catalyst-controll
An Efficient and Regioselective Deprotection Method for Acetylated Glycosides
Li, Jubiao,Wang, Yanguang
, p. 211 - 217 (2007/10/03)
A new regioselective 2-O-deacetylation methodology of acetylated glycosides using 85% hydrazine hydrate in THF is described. Using this method, acetylated 1-thio-glycoside could also be selectively deprotected to give 3-O-deprotected compound.
Synthesis of Trisaccharide of Incanoside from Caryopteris incana
Li, Jubiao,Wang, Yanguang
, p. 515 - 522 (2007/10/03)
Trisaccharide phenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl-(1 → 2)-3,4-di-O-benzoyl-α-L-rhamnopyranosyl-(1 → 3)-2-O-acetyl-4,6-O-benzylidene-1-thio-β-D-glucopyranoside, the sugar core of incanosides from Caryopteris incana (THUNB.), was syn
Synthesis of Vancomycin from the Aglycon
Thompson, Christopher,Ge, Min,Kahne, Daniel
, p. 1237 - 1244 (2007/10/03)
Vancomycin-resistant bacterial strains pose a serious threat to human health. Efforts to overcome vancomycin resistance by modifying the natural product have shown that the carbohydrates help modulate biological activity. To explore the mechanisms by which the carbohydrates function, it would be useful to have access to vancomycin derivatives containing different disaccharides. We now describe the synthesis of vancomycin from a readily available protected aglycon. This chemistry lays the groundwork for wide-ranging investigations of the roles of the carbohydrates in the biological activity of vancomycin. Moreover, in developing methods to glycosylate vancomcyin, we have extended the utility of the sulfoxide glycosylation reaction considerably by making it possible to use unhindered esters as neighboring groups. The chemistry we describe may also have implications for how to improve some other glycosylation methods.
Regioselective Lipase-catalysed acylation of 4,6-O-benzylidene-α- and - β-D-pyranoside derivatives displaying a range of anomeric substituents
Gridley, Jonathan J.,Hacking, Andrew J.,Osborn, Helen M. I.,Spackman, David G.
, p. 14925 - 14946 (2007/10/03)
The application of Lipase enzymes to effect regioselective C-3-O- acylation of 4,6-O-benzylidene-β-D-gluco- and -galactopyranosides displaying a range of anomeric substituents, and C-2-O-acylation of phenyl 4,6-O- benzylidene-α-D-glucopyranoside and ethyl 4,6-O-benzylidene-1-thio-α-D- glucopyranoside is reported. In particular this method has allowed introduction of a variety of acyl protecting groups at the C-3 hydroxyl group of ethyl 4,6-O-benzylidene-1-thio-β-D-glucopyranoside 11.
Regioselective lipase-catalysed acylation of 4,6-O-benzylidene-β-D-pyranoside derivatives displaying a range of anomeric substituents
Gridley, Jonathan J.,Hacking, Andrew J.,Osborn, Helen M. I.,Spackman, David G.
, p. 1397 - 1399 (2007/10/03)
The application of lipase enzymes to effect regioselective C-3-O-acylation of 4,6-O-benzylidene-β-D-gluco- and galactopyranosides displaying a range of anomeric substituents is reported. In particular this method has allowed introduction of a variety of acyl protecting groups at the C-3 hydroxyl group of ethyl 4,6-O-benzylidene-1-thio-β-D-glucopyranoside 9.
