473442-27-2

Upstream product

• 18422-54-3 1,2;4,5-di-O-isopropylidene-β-D-fructopyranose 
• 34626-95-4 1,2:3,4-di-O-isopropylidene-β-D-psicofuranose 
• 58501-81-8 1,2:3,4-di-O-isopropylidene-6-O-p-toluenesulfonyl-β-D-psicofuranose 
• 473442-26-1 1,2-di-O-acetyl-3,4-O-isopropylidene-6-azido-6-deoxy-β-D-ribohexulofuranose 
• 473442-25-0 6-azido-6-deoxy-1,2;3,4-di-O-isopropylidene-β-D-ribohexulofuranose 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 151252-18-5 (3aR,4R,6R,6aR)-6-Azidomethyl-4-hydroxymethyl-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-ol 

Relevant academic research and scientific papers

Synthesis of 1-deoxy-L-gulonojirimycin (L-guloDNJ) and 1-deoxy-D-talonojirimycin (D-taloDNJ)

Carbohydrate based syntheses of azasugars with unusual configurations viz. 1,5-dideoxy-1,5-imino-L-gulitol (L-guloDNJ) and 1,5-dideoxy-1,5-imino-L-talitol (L-taloDNJ) are reported, from D-mannose and D-fructose, respectively. The key steps in both syntheses involved reductive aminative cyclizations. Thus, L-guloDNJ was obtained by reduction of 2,3;4,6-di-O-isopropylidene-5-O-p-toluenesulfonyl-D-mannononitrile with LiAlH4 in DME to give the protected azasugar which upon hydrolysis with HCl afforded crystalline L-guloDNJ as the HCl salt in 29% overall yield. Reduction of 6-azido-1-O-tert-butyldimethylsilyl-2,3-O-isopropylidene-β-D- ribohexulofuranose obtained from D-fructose in six steps, followed by treatment with HCl, afforded L-taloDNJ as an HCl salt in ～10% overall yield.