85422-85-1Relevant academic research and scientific papers
A general approach to C-Acyl glycosides via palladium/copper Co-catalyzed coupling reaction of glycosyl carbothioates and arylboronic acids
Wang, Li-Na,Niu, You-Hong,Cai, Qing-Hui,Li, Qin,Ye, Xin-Shan
, (2021/02/03)
A general and efficient approach to the synthesis of various C-acyl glycosides has been developed via Pd2(dba)3/CuTC co-catalyzed cross-coupling reaction of glycosyl carbothioates with arylboronic acids. The reaction showed a broad s
Addition of Organozinc Reagents to Glycopyranosyl Cyanides: Access to Keto Ester-C-glycosides or Unsaturated Acyl-C-glycosides
Ella Obame, Idriss,Ireddy, Prathap,Guisot, Nicolas E. S.,Nourry, Arnaud,Saluzzo, Christine,Dujardin, Gilles,Dubreuil, Didier,Pipelier, Muriel,Guillarme, Stéphane
supporting information, p. 1735 - 1738 (2018/04/24)
Addition of Reformatsky-type or allylic zinc reagents to 2,3,4,6-tetra-O-benzylglycopyranosyl cyanides led to keto ester-C-glycosides or unsaturated acyl-C-glycosides in moderate to excellent yields in the galactose, glucose, and mannose series.
Improved preparation of 4(5)-aryl-2-(β-d-glucopyranosyl)-imidazoles, the most efficient glucose analogue inhibitors of glycogen phosphorylase
Szennyes, Eszter,Bokor, éva,Batta, Gyula,Docsa, Tibor,Gergely, Pál,Somsák, László
, p. 94787 - 94794 (2016/10/21)
The synthesis of 4(5)-aryl-2-(β-d-glucopyranosyl)-imidazoles, the currently most efficient glucose derived inhibitors of glycogen phosphorylase enzymes was amended and extended by using O-perbenzylated β-d-glucopyranosyl cyanide as the starting material.
Glycosyl iodides. History and recent advances
Meloncelli, Peter J.,Martin, Alan D.,Lowary, Todd L.
scheme or table, p. 1110 - 1122 (2009/09/05)
The use of glycosyl iodides as an effective method for the preparation of glycosides has had a recent resurgence in carbohydrate chemistry, despite its early roots in which these species were believed to be of limited use. Renewed interest in these specie
Efficient stereocontrolled synthesis of C-glycosides using glycosyl donors substituted by propane 1,3-diyl phosphate as the leaving group
Singh, Gurdial,Vankayalapati, Hariprasad
, p. 1727 - 1735 (2007/10/03)
α- and β-Glycosyl cyanides, per-O-acetyl-1,2-O-1-cyanoethylidenes and C-allyl glycopyranosides were efficiently prepared by treatment of 2,3,4-tri-O-acetyl-α,β-L-rhamno-, L-fuco- and 2,3,4,6-tetra-O-acetyl-α,β-D-galactopyranosyl propane-1,3-diyl phosphate
Synthesis of Glycosyl Cyanides by the Reaction of 1-S-Phosphorothioates of Carbohydrates with Trimethylsilyl Cyanide
Kudelska, Wieslawa
, p. 1277 - 1280 (2007/10/03)
A new procedure is described for the synthesis of α,β-glycosyl cyanides by the reaction of per-O-benzylated S-α-D-glycopyranosyl phosphorothioates with trimethylsilyl cyanide in the presence of Lewis acid. Starting S-glycosyl phosphorothioates are prepare
Anionic Additions to Glycosyl Iodides: Highly Stereoselective Syntheses of β C-, N-, and O-Glycosides
Gervay, Jacquelyn,Hadd, Michael J.
, p. 6961 - 6967 (2007/10/03)
Classically, glycosyl halides are activated as glycosyl donors by metal chelation under KoenigsKnorr or Helferich conditions. These reactions often proceed through oxonium formation, and the stereochemical outcome is dictated by the anorneric effect and/or the nature of the protecting group on the C2 hydroxyl. Alternatively, glycosyl halides may undergo direct displacement of the halide by an incoming nucleophile in an SN2 mechanism. The latter reaction is far less common, and before this study it was primarily performed with glycosyl bromides. Having recently shown that both α and βglycosyl iodides could be efficiently generated, we embarked upon an investigation of nucleophilic additions to glycosyl iodides. The studies reported herein show that additions of stabilized anions to α-glycosyl iodides proceed with inversion of stereochemistry to give β-glycosides, even in the absence of a C2 participatory group. Glucosyl, galactosyl, and mannosyl iodides were studied, and the combined results indicate that the reactivity of 2,3,4,6-tetra-O-benzyl-α-D-galactosyl iodide > 2,3,4,6-tetra-O-benzyl-α-D-glucosyl iodide > 2,3,4,6-tetra-O-benzyl-α-D-mannosyl iodide. Both the glucosy] and galactosyl iodides are susceptible to E-2 elimination when treated with highly basic anions. In contrast, the mannosyl iodide undergoes substitution to give the 1,2 cis configuration. The overall sequence involves reaction of an anorneric acetate with trimethylsilyl iodide with in vacua removal of the resulting trimethylsilyl acetate. The iodide is then treated with a nucleophile without further characterization. A variety of nucleophiles were stereoselectively added to the glycosyl halides providing β-, C-, N-, and O-glycosides.
Reactions of Glycosyl Fluorides. Synthesis of C-Glycosides
Nicolaou, K. C.,Dolle, Roland E.,Chucholowski, Alexander,Randall, Jared L.
, p. 1153 - 1154 (2007/10/02)
Glycosyl fluorides were found to react with a number of nucleophilic reagents with or without catalysis leading to a variety of C-glycosides and related compounds.
