461666-81-9

Upstream product

• 108-24-7 acetic anhydride 
• 461666-80-8 Acetic acid (2R,3R,4S,5S)-4-acetoxy-5-acetoxymethyl-2-[(2S,3R,4R,5S)-3,4-dihydroxy-5-(4-methoxy-phenoxy)-tetrahydro-furan-2-ylmethoxy]-tetrahydro-furan-3-yl ester 
• 13035-61-5 1,2,3,6-tetra-O-acetyl-5-deoxy-α-L-arabino-hexofuranose 
• 150-76-5 4-methoxy-phenol 
• 461666-79-5 4'-methoxyphenyl α-L-arabinofuranoside 
• 461666-78-4 Acetic acid (2S,3R,4S,5S)-4-acetoxy-5-acetoxymethyl-2-(4-methoxy-phenoxy)-tetrahydro-furan-3-yl ester 

Relevant academic research and scientific papers

Successful combination of (methoxydimethyl)methyl (MIP) and (2-naphthyl)methyl (NAP) ethers for the synthesis of arabinogalactan-type oligosaccharides

In order to characterise the presumed epitopes of arabinogalactans, isolated from the extract of the cell-cultured Echinacea purpurea, two oligosaccharides were synthesized. The whole synthetic route was based on the successful combination of the (methoxydimethyl)methyl (MIP) and the (2-naphthyl)methyl ether (NAP) protecting groups. A β-(1→6)-linked trigalactoside was prepared, which contained a NAP ether at position 2′.This protecting group was selectively removed using either DDQ or Pd-C/H2 and the acceptor was ready for further glycosylation. We have used two arabinofuranosyl donor compounds: 2,3,5-tri-O-acetyl arabinofuranosyl trichloroacetimidate and a peracetylated α-(1→5)-linked diarabinofuranosyl trichloroacetimidate. For the deprotection of the tetra- and pentasaccharides a common procedure was used. All of the synthesized compounds were characterized by 1H and 13C NMR spectroscopy, as well as by MALDI-TOF mass-spectrometry.