535960-64-6

Upstream product

• 22796-65-2 p-nitrophenyl α-L-arabinofuranoside 
• 108-24-7 acetic anhydride 
• 100-02-7 4-nitro-phenol 
• 56272-01-6 1,2,3,5-tetra-O-acetyl-L-arabinofuranose 
• 535960-65-7 p-nitrophenyl 3,5-di-O-acetyl-α-L-arabinofuranoside 
• 880491-85-0 p-nitrophenyl 2,5-di-O-acetyl-α-L-arabinofuranoside 
• 108-05-4 vinyl acetate 

Downstream Products

• 59997-94-3 p-nitrophenyl 2,3-di-O-acetyl-α-L-arabinofuranoside 
• 535960-67-9 p-nitrophenyl 5-O-(4'-O-acetylferuloyl)-2,3-di-O-acetyl-α-L-arabinofuranoside 

Relevant academic research and scientific papers

Synthesis of 5-deoxy-β-d-galactofuranosides as tools for the characterization of β-d-galactofuranosidases

Derivatives of 5-deoxy-β-d-galactofuranose (5-deoxy-α-l-arabino- hexofuranose) have been synthesized starting from d-galacturonic acid. The synthesis of methyl 5-deoxy-α-l-arabino-hexofuranoside (14α) was achieved by an efficient strategy previously optimized, involving a photoinduced electron transfer (PET) deoxygenation. Compound 14α was converted into per-O-acetyl-5-deoxy-α,β-l-arabino-hexofuranoside (16), an activated precursor for glycosylation reactions. The SnCl4-promoted glycosylation of 16 led to 4-nitrophenyl (19α), and 4-methylthiophenyl 5-deoxy-α-l-arabino-hexofuranosides (20α). The oxygenated analog 4-methylphenyl 1-thio-β-d-galactofuranoside (23β) was also prepared. The 5-deoxy galactofuranosides were evaluated as inhibitors or substrates of the exo-β-d-galactofuranosidase from Penicillium fellutanum, showing that the absence of HO-5 drastically diminishes the affinity for the protein.

The acetates of p-nitrophenyl α-L-arabinofuranoside - Regioselective preparation by action of lipases

All possible di-O-acetates and mono-O-acetates of p-nitrophenyl α-l-arabinofuranoside were prepared by chemoenzymatic way using lipases. The 2,3-di-O-acetate was obtained in 90% yield by deacetylation of the primary acetyl group of per-O-acetylated p-nitr