475672-29-8

Basic information

• Product Name: methyl (2-O-acetyl-4-O-benzyl-α-L-rhamnopyranosyl)-(1->3)-2-acetamido-2-deoxy-4,6-O-isopropylidene-β-D-glucopyranoside
• Synonyms: methyl (2-O-acetyl-4-O-benzyl-α-L-rhamnopyranosyl)-(1->3)-2-acetamido-2-deoxy-4,6-O-isopropylidene-β-D-glucopyranoside
• CAS NO: 475672-29-8
• Molecular Weight: 553.607
• Mol File: 475672-29-8.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: methyl (2-O-acetyl-4-O-benzyl-α-L-rhamnopyranosyl)-(1->3)-2-acetamido-2-deoxy-4,6-O-isopropylidene-β-D-glucopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: methyl (2-O-acetyl-4-O-benzyl-α-L-rhamnopyranosyl)-(1->3)-2-acetamido-2-deoxy-4,6-O-isopropylidene-β-D-glucopyranoside(475672-29-8)
• EPA Substance Registry System: methyl (2-O-acetyl-4-O-benzyl-α-L-rhamnopyranosyl)-(1->3)-2-acetamido-2-deoxy-4,6-O-isopropylidene-β-D-glucopyranoside(475672-29-8)

Safety Data

• Hazardous Substances Data: 475672-29-8(Hazardous Substances Data)

Upstream product

• 1445-45-0 Trimethyl orthoacetate 
• 475672-28-7 methyl (4-O-benzyl-α-L-rhamnopyranosyl)-(1->3)-2-acetamido-2-deoxy-4,6-O-isopropylidene-β-D-glucopyranoside 
• 475672-27-6 methyl (2,3-di-O-acetyl-4-O-benzyl-α-L-rhamnopyranosyl)-(1->3)-2-acetamido-2-deoxy-4,6-O-isopropylidene-β-D-glucopyranoside 

Downstream Products

• 475672-30-1 methyl (2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-(1->3)-(2-O-benzoyl-4-O-benzyl-α-L-rhamnopyranosyl)-(1->3)-(2-O-acetyl-4-O-benzyl-α-L-rhamnopyranosyl)-(1->3)-2-acetamido-2-deoxy-4,6-O-isopropylidene-β-D-glucopyranoside 

Relevant articles and documents

Convergent synthesis, NMR and conformational analysis of tetra- and pentasaccharide haptens of the Shigella flexneri serotype 5a O-specific polysaccharide

Convergent syntheses of the methyl glycosides of the branched pentasaccharide α-L-Rhap-(1→2)-[α-D-Glcp-(1→3)]-α-L-Rhap- (1→3)-α-L-Rhap-(1→3)-β-D-GlcNAcp [A(E)BCD], featuring the biological repeating unit of the O-specific polysaccharide of Shigella flexneri serotype 5a, and of a related linear tetrasaccharide (EBCD) are described. The strategy, based on the trichloroacetimidate methodology, relied on the use of a key EB disaccharide donor and appropriate CD acceptors. The use of an isopropylidene acetal to block OH-4 and OH-6 of residue D was found to be a suitable alternative to the employment of the more commonly used benzylidene acetal. Conformational analysis of EBCD-OMe and A(E)BCD-OMe was based on analysis of 1H and 13C chemical shifts and inter-proton distances data obtained by NMR spectroscopy. The data showed that residue A had no influence on the conformational behaviour of residue E, although these two residues were involved in a 2,3-cis vicinal glycosylation pattern in A(E)BCD-OMe. Comparison of 1H and 13C chemical shifts of the two oligosaccharides with those of their corresponding sequences in the O-specific polysaccharide of S. flexneri 5a showed that the two oligosaccharides presented a distribution of solution conformations similar to that in the O-specific polysaccharide. The conformation of A(E)BCD-OMe was investigated by two approaches: (i) energy minimisation based on ROE-derived distances with the DISCOVER program and (ii) a conformational searching method (the CICADA algorithm interfaced with MM3 force-field), The minimised conformation obtained by the former approach was in total agreement with the average of the two major families of conformations resulting from the CICADA calculations. Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002.