431981-85-0

Basic information

• Product Name: methyl 2,4,6-tri-O-benzoyl-α-D-mannopyranosyl-(1->3)-2,4,6-tri-O-benzoyl-α-D-mannopyranoside
• Synonyms: methyl 2,4,6-tri-O-benzoyl-α-D-mannopyranosyl-(1->3)-2,4,6-tri-O-benzoyl-α-D-mannopyranoside
• CAS NO: 431981-85-0
• Molecular Weight: 980.976
• Mol File: 431981-85-0.mol

Chemical Properties

• CAS DataBase Reference: methyl 2,4,6-tri-O-benzoyl-α-D-mannopyranosyl-(1->3)-2,4,6-tri-O-benzoyl-α-D-mannopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: methyl 2,4,6-tri-O-benzoyl-α-D-mannopyranosyl-(1->3)-2,4,6-tri-O-benzoyl-α-D-mannopyranoside(431981-85-0)
• EPA Substance Registry System: methyl 2,4,6-tri-O-benzoyl-α-D-mannopyranosyl-(1->3)-2,4,6-tri-O-benzoyl-α-D-mannopyranoside(431981-85-0)

Safety Data

• Hazardous Substances Data: 431981-85-0(Hazardous Substances Data)

Upstream product

• 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 
• 431981-83-8 methyl 3-O-allyl-2,4,6-tri-O-benzoyl-α-D-mannopyranosyl-(1->3)-2-O-benzoyl-α-D-mannopyranoside 
• 431981-81-6 methyl 3-O-allyl-2,4,6-tri-O-benzoyl-α-D-mannopyranosyl-(1->3)-4,6-O-benzylidene-α-D-mannopyranoside 
• 500217-15-2 methyl 3-O-allyl-2,4,6-tri-O-benzoyl-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 
• 98-88-4 benzoyl chloride 
• 125226-68-8 methyl 2,4,6-tri-O-benzoyl-α-D-mannopyranoside 
• 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 
• 431981-80-5 3-O-allyl-2,4,6-tri-O-benzoyl-α-D-mannopyranoside trichloroacetimidate 
• 28541-75-5 p-methoxyphenyl α-D-mannopyranoside 
• 67381-27-5 methyl 3-O-allyl-α-D-mannopyranoside 

Relevant articles and documents

Synthesis and heparanase inhibitory activity of sulfated mannooligosaccharides related to the antiangiogenic agent PI-88

A stepwise synthetic route to the mannooligosaccharides from the neutral fraction of Pichia holstii phosphomannan hydrolysate, including a tetrasaccharylamine component, was developed using only two or three readily available d-mannose building blocks. Th

SULFATED OLIGOSACCHARIDE DERIVATIVES

The invention relates to compounds which are polysufated oligosaccharide derivatives having activity as inhibitors of heparan sulfate-binding proteins and inhibitors of the enzyme heparanase; methods for the preparation of the compounds; compositions comprising the compounds, and use of the compounds and compositions thereof for the antiangiogenic, antimetastatic, anti-inflammatory, antimicrobial, anticoagulant and/or antithrombotic treatment, lowering of blood triglyceride levels and inhibition of cardiovascular disease of a mammalian subject.

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.

An efficient and practical synthesis of α-(1→3)-linked mannohexaose and mannooctaose

α-(1→3)-Linked mannohexaose and mannooctaose as their methyl glycosides were synthesized from condensation of the corresponding α-(1→3)-linked di- (9) and tetrasaccharide donor (21) with the tetrasaccharide acceptor (23), respectively, followed by deacylation. The donor 21 and acceptor 23 were prepared readily from activation of C-1 of the tetrasaccharide 20 and deallylation of the tetrasaccharide 22, respectively. The tetrasaccharide 20 was prepared from oxidative cleavage of 1-O-p-methoxyphenyl of 19, which was obtained from coupling of 9 with 11. The tetrasaccharide 22 was obtained from condensation of the donor 13 with the acceptor 18. These disaccharides 9, 11, 13, and 18 were produced easily by simple chemical transformation using p-methoxyphenyl 3-O-allyl-α-D-mannopyranoside (1) and 2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl trichloroacetimidate (6), and methyl 3-O-allyl-α-D-mannopyranoside (14) as the synthons.