Synthesis of N-substituted iminosugars from 2′-carbonyl-C-glycofuranosides

Synthesis and Biological Evaluation of New Dihydrofuro[3,2-b]piperidine Derivatives as Potent α-Glucosidase Inhibitors

“…Selective deprotection of 5- O -acetyl and mesylation of the naked hydroxyl yielded mesylates 3 and 9 . By nucleophilic substitution, mesylates 3 and 9 were reacted with NaN 3 afforded 5-azido- C -ribosides 4 and 10 [ 39 ]. The reduction of the azido group to amine was performed after the terminal oxidation of olefin, which was immediately subject to saturated NaOMe in methanol at room temperature overnight.…”

InCl3Catalyzed Highly Diastereoselective [3 + 2] Cycloaddition of 1,2-Cyclopropanated Sugars with Aldehydes: A Straightforward Synthesis of PersubstitutedBis-Tetrahydrofurans and Perhydrofuro[2,3-b]pyrans

“…Given the important role of the substituted perhydrofuro[2,3- b ]pyrans (and bis -THFs), the lack of utility of cyclopropanated carbohydrates in both Lewis acid and transition metal catalyzed cycloadditions, and as part of our continuing interest in the synthesis of carbohydrate analogues, ,,, we disclose herein our results on an InCl 3 catalyzed [3 + 2] cycloaddition of cyclopropanated sugars and aldehydes. , This reaction offers a mild, efficient method to generate multisubstituted perhydrofuro[2,3- b ]pyrans (and bis -THFs) in high yield with excellent diastereoselectivity (Scheme ). To our knowledge, this is the first successful example that utilizes the [3 + 2] cycloaddition between cyclopropanes and CX (X = C, N, O) compounds to synthesize multisubstituted perhydrofuro[2,3- b ]pyrans and bis -THFs.…”