10028-45-2

Upstream product

• 138906-41-9 4-methoxylphenzyl 2-deoxy-2-phthalimido-3,4,6-tri-O-acetyl-β-D-glucopyranoside 
• 85-44-9 phthalic anhydride 

Downstream Products

• 161767-31-3 Acetic acid (2R,3S,4R,5R,6S)-3-acetoxy-2-acetoxymethyl-6-((2S,3S,4S,5S,6S)-4,5-bis-benzyloxy-6-fluoromethyl-2-methoxy-tetrahydro-pyran-3-yloxy)-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-tetrahydro-pyran-4-yl ester 
• 161767-11-9 methyl O-(2-phthalimido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-(1<*>2)-3-O-methyl-4,6-di-O-benzyl-α-D-mannopyranoside 
• 92733-65-8 tert-butyl 3,6-di-O-benzoyl-2-deoxy-2-phthalimido-β-D-glucopyranoside 
• 92733-67-0 tert-butyl 4-O-acetyl-3,6-di-O-benzoyl-2-deoxy-2-phthalimido-β-D-galactopyranoside 
• 92733-66-9 tert-butyl 3,6-di-O-benzoyl-2-deoxy-4-O-(methylsulfonyl)-2-phthalimido-β-D-glucopyranoside 
• 92733-69-2 4-O-acetyl-3,6-di-O-benzoyl-2-deoxy-2-phthalimido-β-D-galactopyranosyl bromide 
• 92733-68-1 4-O-acetyl-3,6-di-O-benzoyl-2-deoxy-2-phthalimido-α-D-galactopyranosyl bromide 
• 142968-03-4 2-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-1,3-di-O-benzyl-4,6-O-benzylidene-5a-carba-α-D-mannopyranose 
• 146194-28-7 8-(Methoxycarbonyl)octyl 6-O-(2-deoxy-2-phthalimido-β-D-glucopyranosyl)-2,4-di-O-benzyl-α-D-mannopyranoside 
• 146194-25-4 8-(Methoxycarbonyl)octyl 2-O-(2-deoxy-2-phthalimido-β-D-glucopyranosyl)-3,4,6-tri-O-benzyl-α-D-mannopyranoside 
• 146194-29-8 8-(Methoxycarbonyl)octyl 6-O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-2,4-di-O-benzyl-α-D-mannopyranoside 
• 146194-26-5 8-(Methoxycarbonyl)octyl 2-O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-3,4,6-tri-O-benzyl-α-D-mannopyranoside 
• 118466-47-0 allyl 3-O-<3'-O-(3'',4'',6''-tri-O-acetyl-2''-deoxy-2''-phthalimido-β-D-glucopyranosyl)-2'-O-benzoyl-4'-O-benzyl-α-L-rhamnopyranosyl>-2-O-benzoyl-4-O-benzyl-α-L-rhamnopyranoside 
• 118466-48-1 8-methoxycarbonyloctyl 3-O-<3'-O-(3'',4'',6''-tri-O-acetyl-2''-deoxy-2''-phthalimido-β-D-glucopyranosyl)-2'-O-benzoyl-4'-O-benzyl-α-L-rhamnopyranosyl>-2,4-di-O-benzoyl-α-L-rhamnopyranoside 

Relevant academic research and scientific papers

Traceless Staudinger ligation of glycosyl azides with triaryl phosphines: Stereoselective synthesis of glycosyl amides

α-Glycosyl amides can be synthesized from the corresponding O-benzyl-α-glycosyl azides using a traceless Staudinger ligation with diphenylphosphanyl-phenyl esters 4. All the phosphines employed and their phenol precursors are stable to air at 4 °C for months. Fast intramolecular trapping of the reduction intermediates results in the direct formation of the amide link, which, in turn, prevents epimerisation and allows retention of configuration at the anomeric carbon. Yields and α-selectivity are high when the reaction is performed in polar aprotic solvents. Removal of the benzyl ether protecting groups is achieved by catalytic hydrogenation. α-Glycosyl amides represent a class of virtually unexplored nonhydrolyzable monosaccharide derivatives that may find a useful application as sugar mimics. Conformational studies by NMR spectroscopy confirm that deprotected α-glycosyl amides in the gluco, galacto, and fuco series retain the normal pyranose conformation of the monosaccharide. The reaction of phosphines 4 with tetra-O-acetyl-glycosyl azides is nonstereoconservative, and β-glycosyl amides are obtained in good yields and with complete stereoselectivity starting from both α and β azides.

Conversion of p-methoxyphenyl glycosides into the corresponding glycosyl chlorides and bromides, and into thiophenyl glycosides

p-Methoxyphenyl (pMP) β-D-glycopyranosides (Glc, Gal, GlcNPhth, GalNPhth, GlcNTroc, Galβ4Glc, Galα4Gal) were prepared from the corresponding 1-O-acetyl sugars in 79-90% yield, using boron trifluoride etherate as promoter. Treatment of the pMP glycosides with acyl chlorides or bromides in the presence of various Lewis acids gave the corresponding glycosyl chlorides and bromides in 81-98% yield. Treatment of the acyl-protected pMP glycosides with thiophenol and boron trifluoride etherate gave the corresponding thioglycosides in 80-100% yield and high (> 20:1) β/α selectivity. The stability of pMP glycosides was investigated against a series of reagents.