147332-52-3Relevant academic research and scientific papers
S-Adamantyl Group Directed Site-Selective Acylation: Applications in Streamlined Assembly of Oligosaccharides
Blaszczyk, Stephanie A.,Xiao, Guozhi,Wen, Peng,Hao, Hua,Wu, Jessica,Wang, Bo,Carattino, Francisco,Li, Ziyuan,Glazier, Daniel A.,McCarty, Bethany J.,Liu, Peng,Tang, Weiping
supporting information, p. 9542 - 9546 (2019/06/10)
The site-selective functionalization of carbohydrates is an active area of research. Reported here is the surprising observation that the sterically encumbered adamantyl group directed site-selective acylation at the C2 position of S-glycosides through dispersion interactions between the adamantyl C?H bonds and the π system of the cationic acylated catalyst, which may have broad implications in many other chemical reactions. Because of their stability, chemical orthogonality, and ease of activation for glycosylation, the site-selective acylation of S-glycosides streamlines oligosaccharide synthesis and will have wide applications in complex carbohydrate synthesis.
Efficient acetylation of carbohydrates promoted by imidazole
Tiwari, Pallavi,Kumar, Rishi,Maulik, Prakas R.,Misra, Anup Kumar
, p. 4265 - 4270 (2007/10/03)
An efficient per-O-acetylation of carbohydrate derivatives and unprotected reducing sugars promoted by imidazole is reported. The reaction conditions have been successfully employed to acetylate carbohydrate derivatives containing acid-susceptible functional groups. In most of the cases the yields obtained were excellent. Wiley-VCH Verlag GmbH & Co. KGaA, 2005.
InCl3 as a powerful catalyst for the acetylation of carbohydrate alcohols under microwave irradiation
Das, Saibal Kumar,Reddy, K. Anantha,Krovvidi, V. L. Narasimha Rao,Mukkanti
, p. 1387 - 1392 (2007/10/03)
Indium(III) chloride catalyzed microwave assisted acetylation of different carbohydrates is an efficient synthesis of per-O-acetyl derivatives and provides the products in good to excellent yields.
One-pot acetalation-acetylation of sugar derivatives employing perchloric acid immobilised on silica
Mukhopadhyay, Balaram,Russell, David A.,Field, Robert A.
, p. 1075 - 1080 (2007/10/03)
Perchloric acid immobilised on silica gel has been used as an efficient promoter for per-O-acetylation, and acetalation and subsequent O-acetylation of glycosides and thioglycosides in one-pot using stoichiometric reagents.
An efficient and stereoselective synthesis of β-D-Arap-(1 → 2)-β-D-Galp-(1 → 3)-β-D-Galp-(1 → 4)-α-D-Manp, a tetrasaccharide fragment of Leishmania major lipophosphoglycan
Yashunsky, Dmitry V,Higson, Adrian P,Ross, Andrew J,Nikolaev, Andrei V
, p. 243 - 248 (2007/10/03)
A tetrasaccharide fragment of Leishmania major lipophosphoglycan (which seems to be involved in a biological mechanism for the parasite transmission) has been synthesised using the thioglycoside, trichloroacetimidate and halide-exchange glycosylation procedures and step-wise chain elongation strategy.
Regioselective C-3-O-acylation and O-methylation of 4,6-O-benzylidene-β-D-gluco- and galactopyranosides displaying a range of anomeric substituents
Osborn, Helen M.I.,Brome, Victoria A.,Harwood, Laurence M.,Suthers, William G.
, p. 157 - 166 (2007/10/03)
The regioselective C-3-O-acylation and O-methylation of a range of 4,6-O-benzylidene-β-D-gluco- and galactopyranosides has been studied. Regioselectivity is achieved by forming the copper chelate of the 2,3-diol using either sodium hydride and copper(II) chloride, or copper(II) acetylacetanoate, or copper(II) acetate, prior to introduction of the acylating or methylating agent.
