118246-03-0

Basic information

• Product Name: methyl 2,3,4-tri-O-acetyl-O-α-L-rhamnopyranosyI-(1->3)-2-O-benzoyl-4,6-O-benzylidene-O-α-D-gluco-pyranoside
• Synonyms: methyl 2,3,4-tri-O-acetyl-O-α-L-rhamnopyranosyI-(1->3)-2-O-benzoyl-4,6-O-benzylidene-O-α-D-gluco-pyranoside
• CAS NO: 118246-03-0
• Molecular Weight: 658.656
• Mol File: 118246-03-0.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: methyl 2,3,4-tri-O-acetyl-O-α-L-rhamnopyranosyI-(1->3)-2-O-benzoyl-4,6-O-benzylidene-O-α-D-gluco-pyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: methyl 2,3,4-tri-O-acetyl-O-α-L-rhamnopyranosyI-(1->3)-2-O-benzoyl-4,6-O-benzylidene-O-α-D-gluco-pyranoside(118246-03-0)
• EPA Substance Registry System: methyl 2,3,4-tri-O-acetyl-O-α-L-rhamnopyranosyI-(1->3)-2-O-benzoyl-4,6-O-benzylidene-O-α-D-gluco-pyranoside(118246-03-0)

Safety Data

• Hazardous Substances Data: 118246-03-0(Hazardous Substances Data)

Upstream product

• 125520-01-6 ethyl 2,3,4-tri-O-acetyl-1-thio-α-L-rhamnopyranoside 
• 28642-64-0 methyl 2-O-benzoyl-4,6-di-O-benzylidene-α-D-glucopyranoside 
• 7404-35-5 1,2,3,4-tetra-O-acetyl-L-rhamnopyranose 
• 54769-36-7 N-benzoyloxybenzotriazole 
• 5158-64-5 2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl bromide 
• 136809-99-9 phenyl 2,3,4-tri-O-acetyl-1-seleno-α-L-rhamnopyranoside 
• 3162-96-7 4,6-O-benzylidene-1-O-methyl-α-D-glucopyranoside 
• 113893-72-4 2,3,4-tri-O-acetyl-L-rhamnopyranosyl trichloroacetimidate 

Downstream Products

• 221002-67-1 methyl 2-O-benzoyl-3-O-(2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl)-α-D-glucopyranosiduronic acid 
• 221002-64-8 methyl 2,3,4-tri-O-acetyl-O-α-L-rhamnopyranosyl-(1->3)-2-O-benzoyI-O-α-D-glucopyranoside 

Relevant articles and documents

Iron(iii) chloride modulated selective 1,2-trans glycosylation based on glycosyl trichloroacetimidate donors and its application in orthogonal glycosylation

The development of a new glycosylation method for efficient stereoselective synthesis of β-gluco- and galactosides from their corresponding armed trichloroacetimidate donors mediated by 10 mole% of FeCl3 has been focused. FeCl3 has a

Synthesis and nmr characterisation of methyl mono- and DI-0-α-L-rhamnopyranosyl-α-d-glucopyranosiduronic acids

The synthesis and NMR characterisation of methyl mono- and di-O-α-L-rhamnopyranosyl-α-D-glucopyranosiduronic acids 1-6 are described. Two commercial starting products were used: methyl α-D-glucopyranoside 7 for the preparation of 1 and 2, and methyl (R)-4,6-O-benzylidene-α-D-glucopyranoside 8 for 3-6. Oxidation reaction of the hydroxymethyl group of glucose to a carboxylic acid group was performed by sodium hypochlorite 2,2,6,6-tetramethyl-1-piperidinyloxy (TEMPO)-mediated procedure after the coupling reaction. Glycosylation was carried out using the trichloroacetimidate approach with trimethylsilyl trifluoromethanesulfonate (TMSOTf) as promoter, resulting in a completely stereoselective formation of the a glycosyl linkage.

SYNTHESIS AND CONFORMATIONAL ANALYSIS OF METHYL 3-O-MALTOSIDE DERIVATIVES: A BRANCHED TRISACCHARIDE WITH THE CENTRAL GLUCOPYRANOSE RESIDUE IN THE 1C4 CONFORMATION

The branched trisaccharide 4-O-α-D-glucopyranosyl-3-O-α-L-rhamnopyranosyl-β-D-glucopyranose is a model for a part of the lipopolysaccharide from Shigella flexneri serotype I,1a, which has the structure ->2)-α-L-Rha-(1->3)-α-tives, using silver triflate-promoted glycosylation reactions.Similarly, the model disaccharide glucosides methyl 3-O-α-L(and D)-rhamnopyranosyl-α-(and β)-D-glucosides have been synthesized.The acetylated derivatives of the trisaccharides have been converted into their glycosyl bromides (22 and 23) and glycosyl fluorides (24 and25), and the latter transformed into the 1,6-anhydro derivatives by treatment with srong acid base.The conformations of the acetylated derivatives have been analysed by 1H- and 13C-n.m.r. spectroscopy.In most of the branched trisaccharide derivatives, the conformation of the central glucopyranose residue is predominantly 1C4.X-Ray analysis showed that, in the solid state for the glycosyl fluoride 24, the conformation of the central glucopyranose residue is 1C4.