An efficient approach to O-glycosides through CuBr2-Bu4NBr mediated activation of glycosides

Glycosylation Reaction of <i>Thioglycosides</i> by Using Hypervalent Iodine(III) Reagent as an Excellent Promoter

“…General Remarks The 1 H-NMR and 13 C-NMR spectra were recorded by a JEOL JMN-400 spectrometer operating at 400 MHz in CDCl 3 at 25°C with tetramethylsilane as the internal standard. Data are reported as follows: chemical shift in ppm (δ), integration, multiplicity (s=singlet, d=doublet, t=triplet, q=quartet, br s=broad singlet, m=multiplet), coupling constant (Hz).…”

“…[8][9][10][11] The use of copper(II) trifluoromethanesulfonate Cu(OTf) 2 (Mukaiyama) or CuBr 2 -Bu 4 NBr-AgOTf (Ogawa and Ito) as an activator was further investigated. 12,13) Recently, In(OTf) 3 was reported to become an effective activator by ball milling under a solvent-free condition. 14) However, these reported systems for the glycosylation of thioglycosides have relied on a toxic heavy metal oxidant for product formation.…”

An unusual glycosylation product from a partially protected fucosyl donor under silver triflate activation conditions

“…24 It has been established that activation of fucosyl donors in the presence of sterically demanding glycosyl acceptors preferentially form the alpha products via both S N 1 and S N 2 type reaction mechanisms. [25][26][27] These reactions are vital for accessing biologically important fucosides with stereocontrol of the glycosidic linkage. The potential role of partially protected donors in combinatorial approaches towards accessing complex glycoconjugate libraries has been highlighted by Seeberger and co-workers.…”

Stereoselective Total Synthesis of Wheat Flour Ceramide Dihexoside

“…D-Glucosyl acceptor 24 10 -141 was prepared from D-glucose by the synthetic route of Ogawa. 14 1 So we now discuss the synthesis of D-mannosyl donor 23.…”