445397-57-9

Upstream product

• 150-76-5 4-methoxy-phenol 
• 175978-71-9 1,2,4,6-tetra-O-benzoyl-3-O-benzyl-β-L-idopyranose 

Downstream Products

• 1398044-79-5 4-methoxyphenyl 4-O-[6-O-acetyl-2-azido-3-O-benzyl-2-deoxy-4-O-(9-fluorenylmethyloxycarbonyl)-α-D-glucopyranosyl]-2-O-benzoyl-3-O-benzyl-6-O-chloroacetyl-α-L-idopyranoside 
• 1398044-80-8 4-methoxyphenyl 4-O-(6-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-α-D-glucopyranosyl)-2-O-benzoyl-3-O-benzyl-6-O-chloroacetyl-α-L-idopyranoside 
• 1398044-71-7 4-methoxyphenyl 3-O-benzyl-4,6-O-isopropylidene-α-L-idopyranoside 
• 1398044-73-9 4-methoxyphenyl 2-O-benzoyl-3-O-benzyl-α-L-idopyranoside 
• 1398044-89-7 C₄₄H₄₆ClN₃O₁₄ 
• 1398044-72-8 4-methoxyphenyl 2-O-benzoyl-3-O-benzyl-4,6-O-isopropylidene-α-L-idopyranoside 
• 1398044-74-0 4-methoxyphenyl 2-O-benzoyl-3-O-benzyl-6-O-chloroacetyl-α-L-idopyranoside 
• 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 
• 445397-72-8 methyl O-[methyl 2-O-benzoyl-3-O-benzyl-4-O-(4-methoxybenzyl)-α-L-idopyranosyluronate]-(1->3)-(6-O-benzyl-2-deoxy-4-O-pivaloyl-2-trichloroacetamido-β-D-galactopyranosyl)-(1->4)-(methyl 2-O-benzoyl-3-O-benzyl-α-L-idopyranosid)uronate 
• 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 
• 445397-71-7 methyl 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-galactopyranosyl)-(1->4)-(methyl 2-O-benzoyl-3-O-benzyl-α-L-idopyranosid)uronate 
• 445397-73-9 methyl O-[methyl 2-O-benzoyl-3-O-benzyl-4-O-(4-methoxybenzyl)-α-L-idopyranosyluronate]-(1->3)-(2-acetamido-6-O-benzyl-2-deoxy-4-O-pivaloyl-β-D-galactopyranosyl)-(1->4)-(methyl 2-O-benzoyl-3-O-benzyl-α-L-idopyranosid)uronate 
• 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 

Relevant academic research and scientific papers

Synthesis of a targeted library of heparan sulfate hexa- to dodecasaccharides as inhibitors of β-secretase: Potential therapeutics for Alzheimer's disease

Heparan sulfates (HS) are a class of sulfated polysaccharides that function as dynamic biological regulators of the functions of diverse proteins. The structural basis of these interactions, however, remains elusive, and chemical synthesis of defined structures represents a challenging but powerful approach for unravelling the structure-activity relationships of their complex sulfation patterns. HS has been shown to function as an inhibitor of the β-site cleaving enzyme β-secretase (BACE1), a protease responsible for generating the toxic Aβ peptides that accumulate in Alzheimer's disease (AD), with 6-O-sulfation identified as a key requirement. Here, we demonstrate a novel generic synthetic approach to HS oligosaccharides applied to production of a library of 16 hexa- to dodecasaccharides targeted at BACE1 inhibition. Screening of this library provided new insights into structure-activity relationships for optimal BACE1 inhibition, and yielded a number of potent non-anticoagulant BACE1 inhibitors with potential for development as leads for treatment of AD through lowering of Aβ peptide levels. Copyright

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.