445397-84-2

Upstream product

• 445397-83-1 methyl O-(2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-galactopyranosyl)-(1->4)-(3-O-benzyl-α-L-idopyranosyluronic acid)-(1->3)-2-acetamido-6-O-benzyl-2-deoxy-4-O-pivaloyl-β-D-galactopyranoside 
• 445397-79-5 methyl O-(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-idopyranosyluronate)-(1->3)-6-O-benzyl-2-deoxy-4-O-pivaloyl-2-trichloroacetamido-β-D-galactopyranoside 
• 445397-80-8 methyl O-(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-idopyranosyluronate)-(1->3)-4-O-acetyl-6-O-benzyl-2-deoxy-2-trichloroacetamido-β-D-galactopyranoside 
• 445397-81-9 methyl O-(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-idopyranosyluronate)-(1->3)-2-acetamido-6-O-benzyl-2-deoxy-4-O-pivaloyl-β-D-galactopyranoside 
• 445397-82-0 methyl O-(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-idopyranosyluronate)-(1->3)-2-acetamido-4-O-acetyl-6-O-benzyl-2-deoxy-β-D-galactopyranoside 
• 445397-67-1 (methyl 2-O-benzoyl-3-O-benzyl-4-O-chloroacetyl-α-L-idopyranosyluronate)-(1->3)-6-O-benzyl-2-deoxy-4-O-pivaloyl-2-trichloroacetamido-1-O-trichloroacetamidoyl-α-D-galactopyranoside 
• 445397-64-8 4-methoxyphenyl O-(methyl 2-O-benzoyl-3-O-benzyl-4-O-chloroacetyl-α-L-idopyranosyluronate)-(1->3)-6-O-benzyl-2-deoxy-4-O-pivaloyl-2-trichloroacetamido-β-D-galactopyranoside 
• 445397-61-5 4-methoxyphenyl O-(2-O-benzoyl-3-O-benzyl-4,6-O-benzylidene-α-L-idopyranosyl)-(1->3)-6-O-benzyl-2-deoxy-4-O-pivaloyl-2-trichloroacetamido-β-D-galactopyranoside 
• 445397-68-2 (methyl 2-O-benzoyl-3-O-benzyl-4-O-chloroacetyl-α-L-idopyranosyluronate)-(1->3)-4-O-acetyl-6-O-benzyl-2-deoxy-2-trichloroacetamido-1-O-trichloroacetamidoyl-α-D-galactopyranoside 
• 445397-66-0 4-methoxyphenyl O-(methyl 2-O-benzoyl-3-O-benzyl-4-O-chloroacetyl-α-L-idopyranosyluronate)-(1->3)-4-O-acetyl-6-O-benzyl-2-deoxy-2-trichloroacetamido-β-D-galactopyranoside 
• 445397-62-6 4-methoxyphenyl O-(2-O-benzoyl-4,6-O-benzylidene-α-L-idopyranosyl)-(1->3)-4-O-acetyl-6-O-benzyl-2-deoxy-2-trichloroacetamido-β-D-galactopyranoside 
• 445397-63-7 4-methoxyphenyl O-(methyl 2-O-benzoyl-3-O-benzyl-α-L-idopyranosyluronate)-(1->3)-6-O-benzyl-2-deoxy-4-O-pivaloyl-2-trichloroacetamido-β-D-galactopyranoside 
• 445397-87-5 4-methoxyphenyl O-(2-O-benzoyl-3-O-benzyl-α-L-idopyranosyl)-(1->3)-6-O-benzyl-2-deoxy-4-O-pivaloyl-2-trichloroacetamido-β-D-galactopyranoside 
• 445397-65-9 4-methoxyphenyl O-(methyl 2-O-benzoyl-3-O-benzyl-α-L-idopyranosyluronate)-(1->3)-4-O-acetyl-6-O-benzyl-2-deoxy-2-trichloroacetamido-β-D-galactopyranoside 

Relevant academic research and scientific papers

An access to various sulfation patterns in dermatan sulfate: Chemical syntheses of sulfoforms of trisaccharide methyl glycosides

The syntheses are reported for the first time of α-L-IdopA2SO3-(1→3)-β-D-GalpNAc4SO3- (1→4)-α-L-IdopA2SO3-(1→OMe), its disulfated analogue α-L-IdopA2SO3-(1→3)-β-D-GalpNAc-(1→4)- α-L-IdopA2SO3-(1→OMe), and of β-D-GalpNAc4SO3-(1→4)-α-L-IdopA2SO3- (1→3)-β-D-GalpNAc4SO3-(1→OMe), which represent structural fragments of dermatan sulfate, unavailable directly by chemical or enzymatic degradation of the glycosaminoglycan polymer. These molecules were readily obtained from a pair of key disaccharide intermediates, in which the relative difference of stability of the D-GalNAc 4-hydroxy protecting groups (acetate or pivalate) toward saponification conditions allowed access to various sulfoforms from a common precursor. For the preparation of these blocks, the 4-O-pivaloyl-D-galacto moiety was readily obtained through a one-pot stereospecific intramolecular nucleophilic displacement on an easily available 3-O-pivaloyl-D-gluco precursor, and the L-IdoA moiety through selective radical oxidation at C-6 of a L-ido 4,6-diol derivative with oxoammonium salts.