Glycosyl thioimidates

Glycosyl Thioimidates - Preparation and Application as Glycosyl Donors... 

Reaction of glycosyl thioimidate 79 with aa -dibromo-m-xylene in the presence of NaH as a base and 15-crown-5 as a supporting reagent allowed the intermediate 80 (Scheme 4.88). Treatment of the diol 81 with dibutyltin oxide in dry toluene and then reaction with 80 in the presence of tetrabutylammonium iodide afforded the desired O-linked intermediate 82. Activation of this compound with NIS-TMSOTf afforded 83 in a good yield. Hydrogenolysis followed by acetylation gave the desired disac-... 

P. Pomsuriyasak and A. V. Demchenko, Glycosyl thioimidates in a highly convergent one-pot strategy for oligosaccharide synthesis, Tetrahedron Asymmetry, 16 (2005) 433 439. 

Glycosyl Thioimidates as Versatile Glycosyl Donors for Stereoselective f>-Glycosylation and Convergent Oligosaccharide Synthesis... 

A number of different classes of glycosyl thioimidates have been discussed herein. Due to a fairly broad diversity of these derivatives, generalization is often impractical. So far, only S-pyridyl, SBox, and STaz glycosides have been more or less systematically investigated. The following conclusions are primarily focused on the properties of the SBox and STaz glycosides developed by the authors of this overview. 

Glycosyl thioimidates as versatile building blocks for organic synthesis 12KGS229. 

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