29325-33-5Relevant academic research and scientific papers
Thioperoxide-mediated activation of thioglycoside donors
He, Hongwen,Zhu, Xiangming
supporting information, p. 3102 - 3105 (2014/06/23)
Thioperoxide (1) in combination with trimethylsilyl trifluoromethanesulfonate (TMSOTf) provides a powerful thiophilic promoter system, capable of activating different thioglycosides. Both armed and disarmed thioglycosides were activated effectively in the
Stereoselective synthesis of α-glycosyl azides by TMSOTf-mediated ring opening of 1,6-anhydro sugars
Lepage, Mathieu L.,Bodlenner, Anne,Compain, Philippe
, p. 1963 - 1972 (2013/05/21)
Access to α-glycosyl azides in modest to high diastereoselectivity by way of TMSN3 ring-opening of 1,6-anhydro sugars mediated by TMSOTf is reported. The reaction tolerates a wide variety of functional groups including alcohol, alkyne, azide and ester groups. The efficient synthesis of a pseudopentasaccharide in five steps from commercially available levoglucosan by way of a "click-click" approach is presented to highlight the interest of the TMSN3 ring-opening reaction. A new route to α-glycosyl azides by way of TMSN3 ring-opening of 1,6-anhydro sugars is presented. The potential of this methodology is demonstrated by the expeditious synthesis of a pseudopentasaccharide following a "click-click" approach.
Anomeric O-Alkylation, 9. Disaccharide Synthesis via Anomeric O-Alkylation
Tsvetkov, Yury E.,Klotz, Wolfgang,Schmidt, Richard R.
, p. 371 - 376 (2007/10/02)
Base-promoted reaction of tetra-O-benzyl-glucose 1a with secondary alkyl trifluoromethanesulfonates 2 and 3 in toluene provides in the presence of 15-crown-5 preferentially β-glycosides 2aβ and 3aβ, respectively, in high yields.For reactions carried out a
