431981-81-6

Basic information

• Product Name: methyl 3-O-allyl-2,4,6-tri-O-benzoyl-α-D-mannopyranosyl-(1->3)-4,6-O-benzylidene-α-D-mannopyranoside
• Synonyms: methyl 3-O-allyl-2,4,6-tri-O-benzoyl-α-D-mannopyranosyl-(1->3)-4,6-O-benzylidene-α-D-mannopyranoside
• CAS NO: 431981-81-6
• Molecular Weight: 796.825
• Mol File: 431981-81-6.mol

Chemical Properties

• CAS DataBase Reference: methyl 3-O-allyl-2,4,6-tri-O-benzoyl-α-D-mannopyranosyl-(1->3)-4,6-O-benzylidene-α-D-mannopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: methyl 3-O-allyl-2,4,6-tri-O-benzoyl-α-D-mannopyranosyl-(1->3)-4,6-O-benzylidene-α-D-mannopyranoside(431981-81-6)
• EPA Substance Registry System: methyl 3-O-allyl-2,4,6-tri-O-benzoyl-α-D-mannopyranosyl-(1->3)-4,6-O-benzylidene-α-D-mannopyranoside(431981-81-6)

Safety Data

• Hazardous Substances Data: 431981-81-6(Hazardous Substances Data)

Upstream product

• 28541-75-5 p-methoxyphenyl α-D-mannopyranoside 
• 431981-78-1 p-methoxyphenyl 3-O-allyl-2,4,6-tri-O-benzoyl-α-D-mannopyranoside 
• 431981-79-2 3-O-allyl-2,4,6-tri-O-benzoyl-α-D-mannopyranose 
• 319922-17-3 p-methoxyphenyl 3-O-allyl-α-D-mannopyranoside 
• 3162-96-7 methyl-4,6-O-phenylmethylene-α-D-mannopyranoside 

Downstream Products

• 431981-84-9 methyl 3-O-allyl-2,4,6-tri-O-benzoyl-α-D-mannopyranosyl-(1->3)-2,4,6-tri-O-benzoyl-α-D-mannopyranoside 
• 431981-85-0 methyl 2,4,6-tri-O-benzoyl-α-D-mannopyranosyl-(1->3)-2,4,6-tri-O-benzoyl-α-D-mannopyranoside 
• 431981-83-8 methyl 3-O-allyl-2,4,6-tri-O-benzoyl-α-D-mannopyranosyl-(1->3)-2-O-benzoyl-α-D-mannopyranoside 
• 431981-82-7 methyl 3-O-allyl-2,4,6-tri-O-benzoyl-α-D-mannopyranosyl-(1->3)-2-O-benzoyl-4,6-O-benzylidene-α-D-mannopyranoside 

Relevant articles and documents

Synthesis of α-Manp-(1→2)-α-Manp-(1→3)-α-Manp-(1→3)-Manp, the tetrasaccharide repeating unit of Escherichia coli O9a, and α-Manp-(1→2)-α-Manp-(1→2)-α-Manp-(1→3)- α-Manp-(1→3)-Manp, the pentasaccharide repeating unit of E. coli O9 and Klebsiella O3

The tetrasaccharide repeating unit of Escherichia coli O9a, α-D-Manp-(1→2)-α-D-Manp-(1→3)-α-D-Manp- (1→3)-D-Manp, and the pentasaccharide repeating unit of E. coli O9 and Klebsiella O3, α-D-Manp-(1→2)-α-D-Manp-(1→2)-α-D-Manp- (1→3)-α-D-Manp-(1→3)-D-Manp, were synthesized as their methyl glycosides. Thus, selective 3-O-allylation of p-methoxyphenyl α-D-mannopyranoside via a dibutyltin intermediate gave p-methoxyphenyl 3-O-allyl-α-D-mannopyranoside (2) in good yield. Benzoylation (→3), then removal of 1-O-methoxyphenyl (→4), and subsequent trichloroacetimidation afforded the 3-O-allyl-2,4,6-tri-O-benzoyl-α-D-mannopyranosyl trichloroacetimidate (5). Condensation of 5 with methyl 4,6-O-benzylidene-α-D-mannopyranoside (6) selectively afforded the (1→3)-linked disaccharide 7. Benzoylation of 7, debenzylidenation, benzoylation, and deallylation gave methyl 2,4,6-tri-O-benzoyl-α-D-mannopyranosyl-(1→3)-2,4,6-tri-O-benzoyl- α-D-mannopyranoside (11) as the disaccharide acceptor. Coupling of 11 with (1→2)-linked mannose disaccharide donor 17 or trisaccharide donor 21, followed by deacylation, furnished the target tetrasaccharide and pentasaccharide, respectively.