241129-72-6

Upstream product

• 67-56-1 methanol 
• 781657-62-3 phenyl 2,4,6-tri-O-acetyl-1-thio-α/β-L-idopyranose 
• 256348-52-4 2,4,6-tri-O-acetyl-3-O-benzyl-L-idopyranosyl trichloroacetimidate 
• 118711-49-2 1,2,4,6-tetra-O-acetyl-3-O-benzyl-L-idopyranoside 

Downstream Products

• 156977-38-7 methyl 2-O-acetyl-3-O-benzyl-α-L-idopyranoside 
• 156977-40-1 methyl 2-O-acetyl-3-O-benzyl-α-L-idopyranosiduronic acid 
• 156977-42-3 methyl (methyl 2-O-acetyl-3-O-benzyl-α-L-idopyranosid)uronate 
• 181228-43-3 methyl 3-O-benzyl-4,6-O-isopropylidene-α-L-idopyranoside 
• 241129-73-7 Acetic acid (4aS,6R,7R,8S,8aR)-8-benzyloxy-6-methoxy-2,2-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl ester 
• 241129-85-1 (2R,3S,4S,5R,6R)-5-Acetoxy-3-[(2R,3R,4R,5S,6R)-6-acetoxymethyl-3-azido-4-benzyloxy-5-(2-oxo-ethoxy)-tetrahydro-pyran-2-yloxy]-4-benzyloxy-6-methoxy-tetrahydro-pyran-2-carboxylic acid methyl ester 
• 241129-74-8 (2R,3S,4S,5R,6R)-5-Acetoxy-3-((2R,3R,4R,5S,6R)-6-acetoxymethyl-5-allyloxy-3-azido-4-benzyloxy-tetrahydro-pyran-2-yloxy)-4-benzyloxy-6-methoxy-tetrahydro-pyran-2-carboxylic acid methyl ester 
• 241129-75-9 (2R,3S,4S,5R,6R)-5-Acetoxy-3-((2R,3R,4R,5S,6R)-6-acetoxymethyl-3-azido-4-benzyloxy-5-carboxymethoxy-tetrahydro-pyran-2-yloxy)-4-benzyloxy-6-methoxy-tetrahydro-pyran-2-carboxylic acid methyl ester 
• 181228-42-2 methyl 3-O-benzyl-α-L-idopyranoside 

Relevant academic research and scientific papers

Glycosylations of Simple Acceptors with 2-O-Acyl l-Idose or l-Iduronic Acid Donors Reveal Only a Minor Role for Neighbouring-Group Participation

Several l-idose and l-iduronic acid glycosyl donors (mostly thioglycosides but also halides and trichloroacetimidates) with acyl protecting groups at the C-2 position were prepared and evaluated in glycosylation reactions with simple acceptors. In glycosaminoglycan oligosaccharide syntheses in the literature, the presence of C-2 acyl protecting groups in l-ido-configured glycosyl donors generally results in exclusive formation of 1,2-trans glycosidic linkages, a finding that has typically been attributed to neighbouring-group participation. However, glycosylations of simple alcohols with l-ido-configured donors (particularly thioglycosides), reported here, generally displayed incomplete stereocontrol and gave mixtures of the 1,2-trans and 1,2-cis products, suggesting that neighbouring-group participation has lesser importance in these reactions. Glycosyl donors and reaction conditions were identified that gave improved, but not exclusive, selectivity for the desired α-l-anomer (1,2-trans) as the major product. Interestingly, glycosylations under the same reaction conditions with more complex monosaccharide acceptors gave exclusively the expected 1,2-trans products. The role of neighbouring-group participation in these glycosylations was explored with density functional theory (DFT) calculations, which revealed that the non-stereoselective addition of the acceptor alcohol to the intermediate oxocarbenium ion is competitive with the stereospecific addition of the acceptor to the acyloxonium ion intermediate.

Synthesis and biological activity of oligomer-model compounds containing units of a key platelet-binding disaccharide of heparin

A key disaccharide unit in heparin, O-(2-deoxy-2-sulfamido-6-O-sulfo-α-D-glucopyranosyl)-(1→4)-2-O-sulfo-α-L-idop yranosyluronic acid, was previously found to be responsible for the binding interaction of heparin to platelets. A clustering effect to enhance the binding was found to be dependent on the number and frequency of the disaccharide units in a heparin molecule. To systematically examine the clustering effect, three oligomer-model compounds containing two or three units of the disaccharide were synthesized. These compounds inhibited 3H-labelled heparin binding to human platelets more strongly than a compound containing only one unit of the disaccharide.