155585-33-4

Upstream product

• 124-63-0 methanesulfonyl chloride 
• 57099-04-4 3-O-benzyl-1,2-O-isopropylidene-α-D-allofuranose 
• 155585-32-3 3-O-benzyl-1,2-O-isopropylidene-5-O-methylsulfonyl-6-O-triphenylmethyl-α-D-allofuranose 

Downstream Products

• 155585-34-5 (3aR,6R,6aR)-6-benzyloxy-2,2-dimethyl-5-[(2S)-oxiran-2-yl]tetrahydrofuro[2,3-d][1,3]dioxole 
• 155585-24-3 3-O-benzyl-6-deoxy-1,2-isopropylidene-β-L-talofuranose 
• 23537-43-1 5,6-dideoxy-3-O-benzyl-1,2-O-isopropylidene-α-D-xylofuranose 
• 155585-25-4 3-O-benzyl-6-deoxy-1,2-isopropylidene-5-O-methylsulfonyl-β-L-talofuranose 
• 155585-29-8 Trifluoro-methanesulfonic acid (S)-1-((3aR,5S,6R,6aR)-6-benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-ethyl ester 

Relevant academic research and scientific papers

Total synthesis of L-(+)-swainsonine and other indolizidine azasugars from D-glucose

A total synthesis of L-(+)-swainsonine, a potent and specific inhibitor of naringinase, along with the syntheses of six unnatural indolizidine azasugars are reported by starting from D-glucose. L-(+)-Swainsonine was synthesized in 14 steps in 17% overall yield. Further, two of the indolizidine analogues were found to be good glycosidase inhibitors at micromolar concentrations. In all of these syntheses, the key step was an intramolecular SN2 reaction. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.

Fluorination Reactions at C-5 of 3-O-Benzyl-6-deoxy-1,2-isopropylidenehexofuranoses

Fluorination reactions of 2-O-benzyl-6-deoxy-1,2-O-isopropylidene-α-D-gluco-, β-L-ido-, α-D-allo-, and β-L-talo-furanoses (1, 2, 3, and 4) were investigated.The reaction of 1 with diethylaminosulfur trifluoride (DAST) predominantly produced 2-O-benzyl-5,6-dideoxy-5-fluoro-1,2-O-isopropylidene-α-D-glucofuranose with the retention of the configuration at C-5.Both of the fluorides with retained and inverted configurations were obtained in the fluorination of 2 with DAST.In contrast, only the inversion of the configuration occurred when 3 and 4 were reacted with DAST.The reactions of the methanesulfonates of 3 and 4 with tetrabutylammonium fluoride (TBAF) and those of their trifluoromethanesulfonates with tris(dimethylamino)sulfonium difluorotrimethylsilicate (TASF) gave the 5-deoxy-5-fluoro derivatives with the inversion of each configuration and the 5,6-unsaturated derivative.However, the reactions of the sulfonates of 1 and 2 overwhelmingly produced the 4,5- and 5,6-eliminated derivatives.For the reaction in which the steric hindrance of the benzyloxyl group at C-3 and the electronic repulsion of ring oxygen to the SN2 displacement with fluoride anion are significant, such as the fluorination of 1 with DAST, the SNi mechanism is reasonable.