99701-64-1Relevant academic research and scientific papers
Organocatalytic direct α-selective N-glycosylation of amide with glycosyl trichloroacetimidate
Li, Shanji,Kobayashi, Yusuke,Takemoto, Yoshiji
, p. 768 - 770 (2018)
Through the synergistic catalytic effect of the halogen bond (XB) donor and thiourea catalyst, a direct α-selective N-glycosylation of the amide residue of asparagine derivative was achieved using readily accessible glycosyl trichloroacetimidate. n-Butyl methyl ether was found to be the most suitable solvent for the α-selectivity.
Chemoselectivity in Self-Promoted Glycosylation: N- vs. O-Glycosylation
Pedersen, Christian Marcus,Pinna, Alessandro
supporting information, (2020/06/23)
Self-promoted glycosylation using trichloroacetimidates and sulfonamides have recently been developed. In this communication, we study the parameters controlling the chemoselectivity between a nucleophilic sulfonamide nitrogen and an alcohol, both contain
Rearrangement of Benzylic Trichloroacetimidates to Benzylic Trichloroacetamides
Adhikari, Arijit A.,Suzuki, Tamie,Gilbert, Reesheda T.,Linaburg, Matthew R.,Chisholm, John D.
, p. 3982 - 3989 (2017/04/11)
The rearrangement of allylic trichloroacetimidates is a well-known transformation, but the corresponding rearrangement of benzylic trichloroacetimidates has not been explored as a method for the synthesis of benzylic amines. Conditions that provide the tr
Investigations of scope and mechanism of nickel-catalyzed transformations of glycosyl trichloroacetimidates to glycosyl trichloroacetamides and subsequent, atom-economical, one-step conversion to α-urea-glycosides
McKay, Matthew J.,Park, Nathaniel H.,Nguyen, Hien M.
supporting information, p. 8691 - 8701 (2014/07/21)
The development and mechanistic investigation of a highly stereoselective methodology for preparing α-linked-urea neo-glycoconjugates and pseudo-oligosaccharides is described. This two-step procedure begins with the selective nickel-catalyzed conversion of glycosyl trichloroacetimidates to the corresponding α-trichloroacetamides. The α-selective nature of the conversion is controlled with a cationic nickel(II) catalyst, [Ni(dppe)(OTf)2] (dppe=1,2-bis(diphenylphosphino)ethane, OTf=triflate). Mechanistic studies have identified the coordination of the nickel catalyst with the equatorial C2-ether functionality of the α-glycosyl trichloroacetimidate to be paramount for achieving an α-stereoselective transformation. A cross-over experiment has indicated that the reaction does not proceed in an exclusively intramolecular fashion. The second step in this sequence is the direct conversion of α-glycosyl trichloroacetamide products into the corresponding α-urea glycosides by reacting them with a wide variety of amine nucleophiles in presence of cesium carbonate. Only α-urea-product formation is observed, as the reaction proceeds with complete retention of stereochemical integrity at the anomeric C-N bond.
Stereoselective rearrangement of trichloroacetimidates: application to the synthesis of α-glycosyl ureas
Park, Nathaniel H.,Nguyen, Hien M.
supporting information; experimental part, p. 2433 - 2436 (2009/11/30)
A new method for the stereoselective synthesis of r-glycosyl ureas, via nickel-catalyzed [1,3]-rearrangement of glycosyl trichloroacetimidates, has been developed. The r-stereoselectivity at the anomeric carbon of the resulting trichloroacetamides depends
Acid-catalysed rearrangement of glycosyl trichloroacetimidates: a novel route to glycosylamines
Larsen, Kim,Olsen, Carl Erik,Motawia, Mohammed Saddik
, p. 383 - 387 (2008/09/19)
A novel route to glycosylamines has been developed. Treatment of glycosyl trichloroacetimidates with TMSOTf under glycosylation conditions, but in the absence of an acceptor, resulted in complete rearrangement of the trichloroacetimidates into the corresp
O-Glycosyl Imidates, 19. - Reactions of Glycosyl Trichloroacetimidates with Silylated C-Nucleophiles
Hoffmann, Michael G.,Schmidt, Richard R.
, p. 2403 - 2419 (2007/10/02)
Reaction of O-benzyl-protected α-glycopyranosyl trichloroacetimidates 1 and the xylo analogues 7 with silyl enol ethers or allyltrimethylsilane as C-nucleophiles yields with zink chloride as catalyst mainly or exclusively α-C-glycosides (5a-α to 5h-α, 8b,
