69927-20-4

Basic information

• Product Name: methyl 2,3,5-tri-O-benzoyl-αβ-D-lyxofuranoside
• CAS NO: 69927-20-4
• Molecular Weight: 476.483
• Mol File: 69927-20-4.mol
• Article Data: 9

Chemical Properties

• CAS DataBase Reference: methyl 2,3,5-tri-O-benzoyl-αβ-D-lyxofuranoside(CAS DataBase Reference)
• NIST Chemistry Reference: methyl 2,3,5-tri-O-benzoyl-αβ-D-lyxofuranoside(69927-20-4)
• EPA Substance Registry System: methyl 2,3,5-tri-O-benzoyl-αβ-D-lyxofuranoside(69927-20-4)

Safety Data

• Hazardous Substances Data: 69927-20-4(Hazardous Substances Data)

Upstream product

• 25545-03-3 β-D-arabinofuranose 
• 532-20-7 D-arabinofuranose 
• 67-56-1 methanol 
• 87-72-9 L-(+)-arabinose 
• 98-88-4 benzoyl chloride 
• 3795-69-5 methyl β-L-arabinofuranoside 
• 1824-96-0 Methyl α-lyxofuranoside 
• 79083-42-4 methyl D-arabinofuranoside 
• 28697-53-2 D-arabinopyranose 
• 56607-40-0 methyl D-arabinofuranoside 
• 4348-68-9 2,3,5-tri-O-benzoyl-α-D-arabinofuranosyl bromide 
• 70051-90-0 tri-O-benzoyl-β-D-arabinofuranosyl bromide 
• 10323-20-3 D-Arabinose 

Downstream Products

• 4348-68-9 2,3,5-tri-O-benzoyl-α-D-arabinofuranosyl bromide 
• 502761-66-2 C₁₃H₁₆O₆C₁₄H₈O₂ 
• 171074-30-9 (2S,3R,5R)-3-Azido-2-benzoyloxy-5-(2',3',5'-tri-O-benzoyl-α-D-arabinofuranosyloxy)cyclohexanone ethylene dithioacetal 
• 171074-29-6 (2S,3R,5R)-2,3-Dibenzoyloxy-5-(2',3',5'-tri-O-benzoyl-α-D-arabinofuranosyloxy)cyclohexanone ethylene dithioacetal 
• 171074-32-1 (2S,3R,5R)-3-Azido-2-benzoyloxy-5-(2',3',5'-tri-O-benzoyl-α-D-arabinofuranosyloxy)cyclohexanone O-benzyl oxime 
• 171074-33-2 (2S,3R,5R)-3-Azido-2-hydroxy-5-(α-D-arabinofuranosyloxy)cyclohexanone O-benzyl oxime 
• 1276043-29-8 3,5-di-O-benzoyl-β-D-lyxofuranose-1,2-(pent-4-enyl orthobenzoate) 
• 1431370-34-1 3,5-di-O-benzoyl-β-D-arabinofuranoside-prop-2-ynyl-1,2-orthobenzoate 
• 1431370-38-5 (pent-4-enyl) 2,3,5-tri-O-benzoyl-α-D-arabinofuranoside 
• 103702-71-2 benzyl 2,3,5-tri-O-benzoyl-α-D-arabinofuranoside 
• 1431370-40-9 benzyl N-(benzyloxycarbonyl)-O-(2,3,5-tri-O-benzoyl-α-D-arabinofuranosyl)-L-serinate 
• 1431370-42-1 methyl 2,3,6-tri-O-benzyl-4-O-(2,3,5-tri-O-benzoyl-α-D-arabinofuranosyl)-α-D-glucopyranoside 
• 1431370-43-2 pent-4-enyl 2,3,4-tri-O-benzyl-6-O-(2,3,5-tri-O-benzoyl-α-D-arabinofuranosyl)-α-D-mannopyranoside 
• 1431370-45-4 propargyl 3,5-di-O-benzyl-2-O-(2,3,5-tri-O-benzoyl-α-D-arabinofuranosyl)-α-D-arabinofuranoside 

Relevant articles and documents

Total Synthesis of a Partial Structure from Arabinogalactan and Its Application for Allergy Prevention

Arabinogalactan, a microheterogeneous polysaccharide occurring in plants, is known for its allergy-protective activity, which could potentially be used for preventive allergy treatment. New treatment options are highly desirable, especially in a preventive manner, due to the constant rise of atopic diseases worldwide. The structural origin of the allergy-protective activity of arabinogalactan is, however, still unclear and isolation of the polysaccharide is not feasible for pharmaceutical applications due to a variation of the activity of the natural product and contaminations with endotoxins. Therefore, a pentasaccharide partial structure was selected for total synthesis and subsequently coupled to a carrier protein to form a neoglycoconjugate. The allergy-protective activity of arabinogalactan could be reproduced with the partial structure in subsequent in vivo experiments. This is the first example of a successful simplification of arabinogalactan with a single partial structure while retaining its allergy-preventive potential.

Automated solid phase synthesis of oligoarabinofuranosides

Automated solid phase synthesis enables rapid access to the linear and branched arabinofuranoside oligosaccharides. A simple purification step is sufficient to provide the conjugation ready oligosaccharides in good yield.

Ready preparation of furanosyl n-pentenyl orthoesters from corresponding methyl furanosides

The 3,5-di-O-benzoyl n-pentenyl orthoesters of the four pentofuranoses have been prepared. The first key intermediate in each case is the methyl pentofuranoside(s), and a user-friendly procedure for the preparation of each, based on the Callam-Lowary precedent, is described, whereby formation of the crucial α/β anomeric mixture is optimized. The mixture is used directly to prepare the corresponding perbenzoylated pentofuranosyl bromide(s) and then the title compounds.