334834-20-7

Upstream product

• 134198-40-6 6-O-benzoyl-3-O-benzyl-1,2-O-isopropylidene-5-O-methanesulfonyl-α-D-glucofuranose 
• 334834-37-6 1,6-anhydro-2,3,4-triO-trimethylsilyl-β-L-idopyranose 
• 42926-91-0 3-O-benzyl-1,6-anhydro-β-L-idopyranose 
• 60619-47-8 1,6-anhydro-β-L-idopyranose 
• 87357-54-8 6-deoxy-1,2:3,5-di-O-isopropylidene-α-D-xylo-hex-5-enofuranose 
• 81562-09-6 6-hydroxy-1,2:3,5-di-O-isopropylidene-α-D-glucofuranoside 
• 358-23-6 trifluoromethylsulfonic anhydride 
• 334834-19-4 1,6-anhydro-2-O-benzoyl-3-O-benzyl-β-L-idopyranoside 

Relevant academic research and scientific papers

Biologically potent L-hexoses and 6-deoxy-L-hexoses: Their syntheses and applications

This account describes our recent work in the development of new methodologies to prepare rare and biologically potent L-hexoses and 6-deoxy-L-hexoses, from cheapest D-glucose, via L-hexofuranoses and 1,6-anhydro-β-L-hexopyranoses as key building blocks. Their applications in the syntheses of heparin oligosaccharides, the carbohydrate moiety of bleomycin A2, and L-acovenose are also summarized here.

From D-Glucose to Biologically Potent L-Hexose Derivatives: Synthesis of α-L-Iduronidase Fluorogenic Detector and the Disaccharide Moieties of Bleomycin A2 and Heparan Sulfate

A novel and convenient route for the synthesis of biologically potent and rare L-hexose derivatives from D-glucose is described. Conversion of diacetone-α-D-glucose (14) into 1,2:3,5-di-O-isopropylidene-β -L-idofuranose (19) was efficiently carried out in two steps. Orthogonal isopropylidene rearrangement of compound 19 led to 1,2:5,6-di-O-isopropylidene-β-L-idofuranose (27), which underwent regioselective epimerization at the C3 position to give the L-talo- and 3-functionalized L-idofuranosyl derivatives. Hydrolysis of compound 19 under acidic conditions furnished 1,6-anhydro-β-L-idopyranose (35) in excellent yield, which was successfully transformed into the corresponding L-allo, L-altro, L-gulo, and L-ido derivatives via regioselective benzylation, benzoylation, triflation and nucleophilic substitution as the key steps. Applications of these 1,6-anhydro-β-L-hexopyranoses as valuable building blocks to the syntheses of 4-methylcoumarin-7-yl-α-L-iduronic acid and the disaccharide moieties of bleomycin A2 as well as heparan sulfate are highlighted.