130847-19-7

Upstream product

• 100-39-0 benzyl bromide 
• 132799-03-2 ethyl 4-O-benzyl-1-thio-α-L-rhamnopyranoside 
• 1125-88-8 benzaldehyde dimethyl acetal 

Downstream Products

• 163226-14-0 Ethyl 3,4-di-O-benzyl-2-O-(3-carboxypropanoyl)-1-thio-α-L-rhamnopyranoside 
• 172296-74-1 Ethyl 3,4-di-O-benzyl-2-O-(2-carboxybenzoyl)-1-thio-α-L-rhamnopyranoside 
• 172296-77-4 Ethyl 3,4-di-O-benzyl-2-O-(2-tert-butyloxycarbonylethanoyl)-1-thio-α-L-rhamnopyranoside 
• 163226-13-9 ethyl 2-O-benzoyl-3,4-di-O-benzyl-1-thio-α-L-rhamnopyranoside 
• 1622317-97-8 ethyl (2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-(1→3)-(2,4-di-O-benzyl-α-L-rhamnopyranosyl)-(1→2)-3,4-di-O-benzyl-1-thio-α-L-rhamnopyranoside 
• 1437303-53-1 ethyl 3,4-di-O-benzyl-2-O-(p-methoxybenzyl)-1-thio-α-L-rhamnoside 
• 1437303-56-4 phenyl [3,4-di-O-benzyl-2-O-(p-methoxybenzyl)-α-L-rhamnopyranosyl]-(1→3)-2,3,6-tribenzyl-1-thio-β-D-glucopyranoside 
• 1437303-55-3 phenyl [3,4-di-O-benzyl-2-O-(p-methoxybenzyl)-α-L-rhamnopyranosyl]-(1→3)-2,3,6-tri-benzoyl-1-thio-β-D-glucopyranoside 
• 1269776-99-9 ethyl (2,3,5,6-tetra-O-benzyl-α-D-galactofuranosyl)-(1->2)-3,4-di-O-benzyl-1-thio-α-D-rhamnopyranoside 
• 1192175-04-4 ethyl 3,4-di-O-benzoyl-2-O-methyl-1-thio-α-L-rhamnopyranoside 
• 172296-78-5 Ethyl 3,4-di-O-benzyl-2-O-(2-carboxyethanoyl)-1-thio-α-L-rhamnopyranoside 
• 163226-23-1 Ethyl 2-O-<(2-O-benzoyl-1,6-di-O-benzyl-α-D-glucopyranos-3-yloxy)carbonylpropanoyl>-3,4-di-O-benzyl-1-thio-α-L-rhamnopyranoside 

Relevant academic research and scientific papers

Synthesis and solution-phase conformation of the RG-I fragment of the plant polysaccharide pectin reveals a modification-modulated assembly mechanism

The syntheses of pure RG-I fragments of key plant matrix biomolecule pectin using a counterintuitive late-stage convergent cis-glycosylation has allowed detailed analyses of their solution-phase conformations, metal binding affinities, pKa values, self-assembly equilibria, and diffusional kinetics. These reveal a striking, right-handed 31-helix that provides an effective and repeating lateral display of putative liganding carboxylates. Moreover, these heteropolymeric structures allow units as short as tetrasaccharides to self-assemble through carbohydrate-carbohydrate interactions that are induced by the presence of Ca(II), a known dynamic trigger in planta. These self-assembly properties can be switched simply by the addition or removal of a single methyl group in this repeating unit through methyl (de)esterification, another known dynamic trigger in planta. Together, the combined effect of Ca(II) and methylation revealed here suggests a concerted molecular basis for these two major dynamic modifications in planta.

Synthesis of the α-D-GlcpA-(1 → 3)-α-L-Rhap-(1 → 2)-L-Rha trisaccharide isolated from the cell wall hydrolyzate of the green alga, Chlorella vulgaris

The title trisaccharide was synthesized from 6-O-acetyl-2,3,4-tri-O-benzyl-α-D-glucopyranosyl chloride (10), ethyl 2,4-di-O-benzyl-1-thio- (5) and benzyl 3,4-di-O-benzyl-α-L-rhamnopyranoside (9). The disaccharide 11 obtained from compounds 5 and 10 was used as the glycosyl donor to glycosylate the rhamnopyranoside derivative 9 having free OH-2 using the NIS-AgOTf-mediated glycosylation methodology. Zemplen deacetylation of the trisaccharide 12 resulted in the 6″-OH derivative (13), which was selectively oxidized with CrO3 to the uronic acid derivative 14. The benzyl groups were removed by catalytic hydrogenolysis to furnish the target trisaccharide (1).

Intramolecular Glycosylation of Prearranged Glycosides. A Novel Tool for Controlling the Reactivity and Anomeric Selectivity of Glycosylations

The intramolecular (1->4) glycosylation of partially protected alkyl gluco- and galactosides with ethyl 1-thio-rhamnoside that is preconnected via position 2 with a succinyl spacer to positions 3 and 6, respectively of the glycosyl acceptor affords the co

Prearranged Glycosides, 2. Intramolecular Glycosylation of Prearranged Saccharides as a Novel Strategy for the Construction of β-L-Rhamnosidic Linkages

Disaccharides containing a β-L-rhamnosyl residue were prepared by a novel intramolecular glycosylation strategy.Thus, suitably benzyl-protected L-rhamnosyl donors (ethyl and phenyl 1-thiorhamnoside 7, 18) were prearranged in positions 2 and 3 with benzyl 2-O-benzoyl-4,6-O-benzylidene-α-D-glucopyranoside 8 in position 3 by a malonyl, succinyl and phthaloyl bridge, respectively, to give the corresponding conected saccharides 9, 12, 16 and 20.After regioselective opening of the benzylidene ring of the glucoside residue to give compounds 10, 13, 17 and 21, the latter afforded the 3,2'- and 3,3'-bridged disaccharides 22-25 upon intramolecular glycosylation with a thiophilic reagent.The anomeric selectivity of this intramolecular glycosylation is strongly influenced by the nature of the alkanoyl and aroyl bridge, its position at the rhamnosyl residue and the solvent used for the coupling.Best results were obtaind in acetonitrile with the succinyl "spacer" attached to position 2 of the phenyl 1-thiorhamnoside and position 3 of the glucoside that afforded the corresponding β-(1->4)-linked disaccharide 22β in 76percent yield. - Keywords: Carbohydrates / Disaccharides / Glycosylation, intramolecular / β-L-Rhamnoside