321380-16-9

Upstream product

• 175978-71-9 1,2,4,6-tetra-O-benzoyl-3-O-benzyl-β-L-idopyranose 
• 67-56-1 methanol 
• 181024-52-2 methyl 2,4,6-tri-O-benzoyl-3-O-benzyl-α-L-idopyranoside 
• 181228-42-2 methyl 3-O-benzyl-α-L-idopyranoside 
• 98-88-4 benzoyl chloride 
• 181228-43-3 methyl 3-O-benzyl-4,6-O-isopropylidene-α-L-idopyranoside 

Downstream Products

• 321380-47-6 methyl (4-O-acetyl-3,6-di-O-benzyl-2-deoxy-2-trichloroacetamido-β-D-galactopyranosyl)-(1->4)-(methyl 2-O-benzoyl-3-O-benzyl-α-L-idopyranosid)uronate 
• 321380-51-2 methyl (2-acetamido-4-O-acetyl-3,6-di-O-benzyl-2-deoxy-β-D-galactopyranosyl)-(1->4)-(methyl 2-O-benzoyl-3-O-benzyl-α-L-idopyranosid)uronate 
• 321380-67-0 (2R,3S,4R,5R,6R)-3-((2S,3R,4R,5R,6R)-3-Acetylamino-4-benzyloxy-6-benzyloxymethyl-5-hydroxy-tetrahydro-pyran-2-yloxy)-4-benzyloxy-5-hydroxy-6-methoxy-tetrahydro-pyran-2-carboxylic acid 
• 321380-20-5 methyl 2-O-benzoyl-3-O-benzyl-4,6-di-O-tert-butyldimethylsilyl-α-L-idopyranoside 
• 321380-62-5 (2R,3S,4R,5R,6R)-5-Benzoyloxy-4-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-6-methoxy-tetrahydro-pyran-2-carboxylic acid 
• 321380-24-9 methyl (methyl 2-O-benzoyl-3-O-benzyl-4-O-tert-butyldimethylsilyl-α-L-idopyranosid)uronate 
• 321380-28-3 methyl (methyl 2-O-benzoyl-3-O-benzyl-α-L-idopyranosid)uronate 

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.

Syntheses of β-D-GalpNAc4SO3-(1→4)-L-IdopA2SO3, a disaccharide fragment of dermatan sulfate, and of its methyl α-L-glycoside derivative

The syntheses of sodium (sodium 2-acetamido-2-deoxy-4-O-sulfonato-β-D-galactopyranosyl)-(1→4)-(sodium 2-O-sulfonato-L-idopyran)uronate, a disaccharide fragment of dermatan sulfate, and of its methyl α-L-glycoside derivative are reported for the first time. The use of 4-O-acetyl-3,6-di-O-benzyl-2-deoxy-2-trichloroacetamido-1-O-trichloroaceti midoyl-α-D-galactopyranose, readily prepared from a D-gluco precursor, allowed the stereocontrolled and high yielding coupling with the low reactive 4-hydroxyl group of L-iduronic acid ester derivatives. Classical transformation of the disaccharide products into the target molecules was achieved in high yield. (C) 2000 Elsevier Science Ltd.