151252-12-9

Basic information

• Product Name: .alpha.-L-Tagatofuranose, 6-azido-6-deoxy-3,4-O-(1-methylethylidene)-, 1,2-diacetate
• Synonyms: .alpha.-L-Tagatofuranose, 6-azido-6-deoxy-3,4-O-(1-methylethylidene)-, 1,2-diacetate
• CAS NO: 151252-12-9
• Molecular Formula: C13H19 N3 O7
• Molecular Weight: 329.31
• Mol File: 151252-12-9.mol
• Article Data: 1

Chemical Properties

• Appearance: /
• CAS DataBase Reference: .alpha.-L-Tagatofuranose, 6-azido-6-deoxy-3,4-O-(1-methylethylidene)-, 1,2-diacetate(CAS DataBase Reference)
• NIST Chemistry Reference: .alpha.-L-Tagatofuranose, 6-azido-6-deoxy-3,4-O-(1-methylethylidene)-, 1,2-diacetate(151252-12-9)
• EPA Substance Registry System: .alpha.-L-Tagatofuranose, 6-azido-6-deoxy-3,4-O-(1-methylethylidene)-, 1,2-diacetate(151252-12-9)

Safety Data

• Hazardous Substances Data: 151252-12-9(Hazardous Substances Data)

Upstream product

• 58501-81-8 1,2:3,4-di-O-isopropylidene-6-O-p-toluenesulfonyl-β-D-psicofuranose 
• 34626-95-4 1,2:3,4-di-O-isopropylidene-β-D-psicofuranose 
• 18422-54-3 1,2;4,5-di-O-isopropylidene-β-D-fructopyranose 
• 108-24-7 acetic anhydride 
• 473442-25-0 6-azido-6-deoxy-1,2;3,4-di-O-isopropylidene-β-D-ribohexulofuranose 

Downstream Products

• 473442-27-2 (3aR,4R,6R,6aR)-6-Azidomethyl-4-(tert-butyl-dimethyl-silanyloxymethyl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-ol 
• 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 articles and documents

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.