40268-95-9

Basic information

• Product Name: methyl 1,2,3,4-tetra-O-acetyl-α,β-D-glucopyranosyluronate
• CAS NO: 40268-95-9
• Molecular Weight: 376.317
• Mol File: 40268-95-9.mol
• Article Data: 22

Chemical Properties

• CAS DataBase Reference: methyl 1,2,3,4-tetra-O-acetyl-α,β-D-glucopyranosyluronate(CAS DataBase Reference)
• NIST Chemistry Reference: methyl 1,2,3,4-tetra-O-acetyl-α,β-D-glucopyranosyluronate(40268-95-9)
• EPA Substance Registry System: methyl 1,2,3,4-tetra-O-acetyl-α,β-D-glucopyranosyluronate(40268-95-9)

Safety Data

• Hazardous Substances Data: 40268-95-9(Hazardous Substances Data)

Upstream product

• 82228-14-6 methyl D-glucopyranuronate 
• 108-24-7 acetic anhydride 
• 67-56-1 methanol 
• 63-29-6 D-glucurono-6,3-lactone 
• 487-44-5 D-(+)-glucuronic acid γ-lactone 
• 6556-12-3 D-glucuronic acid 
• 1190935-89-7 D-glucurono-6,3-lactone 

Downstream Products

• 174264-49-4 (2S,3S,4S,5R,6S)-3,4,5-Triacetoxy-6-{2-[4-(tert-butyl-dimethyl-silanyloxy)-phenyl]-3-[4-(2-piperidin-1-yl-ethoxy)-benzoyl]-benzo[b]thiophen-6-yloxy}-tetrahydro-pyran-2-carboxylic acid methyl ester 
• 67776-38-9 2,3,4-tri-O-acetyl-1-azido-1-deoxy-β-D-glucopyranuronic acid methyl ester 
• 14365-73-2 2,3,4-tri-O-acetyl-β-D-glucopyranosylamine uronic acid methyl ester 
• 1350467-71-8 methyl (phenyl 2,3-di-O-acetyl-4-deoxy-1-thio-α-L-threo-hex-4-enopyranosid)uronate 
• 52173-67-8 methyl (2,4,6-trichlorophenyl 2,3,4-tri-O-acetyl-β-D-glucopyranosid)uronate 
• 1350467-75-2 methyl (2,4,6-trichlorophenyl 2,3-di-O-acetyl-4-deoxy-α-L-threo-hex-4-enopyranosid)uronate 
• 1350467-76-3 C₁₇H₁₅⁽²⁾H₂Cl₃O₈ 
• 1350467-77-4 methyl (2,4,6-trichlorophenyl 2,3-di-O-acetyl-4-deoxy-5-C-bromo-4-{²H}-β-D-glucopyranosid)uronate 
• 1350467-78-5 methyl (2,4,6-trichlorophenyl 2,3-di-O-acetyl-4-deoxy-4-{(2)H}-α-L-threo-hex-4-enopyranosid)uronate 
• 1350467-79-6 methyl (phenyl 4-deoxy-5-C-methoxy-β-D-glucopyranosid)uronate 
• 1350467-81-0 phenyl 4-deoxy-5-C-methoxy-β-D-glucopyranosiduronic acid 
• 1350467-68-3 phenyl 4-deoxy-1-thio-α-L-threo-hex-4-enopyranosiduronic acid 
• 1350467-69-4 2,4,6-trichlorophenyl 4-deoxy-α-L-threo-hex-4-enopyranosiduronic acid 
• 1350467-70-7 2,4,6-trichlorophenyl 4-deoxy-4-{(2)H}-α-L-threo-hex-4-enopyranosiduronic acid 

Relevant articles and documents

Efficient acetylation of carbohydrates promoted by imidazole

An efficient per-O-acetylation of carbohydrate derivatives and unprotected reducing sugars promoted by imidazole is reported. The reaction conditions have been successfully employed to acetylate carbohydrate derivatives containing acid-susceptible functional groups. In most of the cases the yields obtained were excellent. Wiley-VCH Verlag GmbH & Co. KGaA, 2005.

Potent and Prolonged Innate Immune Activation by Enzyme-Responsive Imidazoquinoline TLR7/8 Agonist Prodrug Vesicles

Synthetic immune-stimulatory drugs such as agonists of the Toll-like receptors (TLR) 7/8 are potent activators of antigen-presenting cells (APCs), however, they also induce severe side effects due to leakage from the site of injection into systemic circulation. Here, we report on the design and synthesis of an amphiphilic polymer-prodrug conjugate of an imidazoquinoline TLR7/8 agonist that in aqueous medium forms vesicular structures of 200 nm. The conjugate contains an endosomal enzyme-responsive linker enabling degradation of the vesicles and release of the TLR7/8 agonist in native form after endocytosis, which results in high in vitro TLR agonist activity. In a mouse model, locally administered vesicles provoke significantly more potent and long-lasting immune stimulation in terms of interferon expression at the injection site and in draining lymphoid tissue compared to a nonamphiphilic control and the native TLR agonist. Moreover, the vesicles induce robust activation of dendritic cells in the draining lymph node in vivo.

A combinatorial approach towards the synthesis of non-hydrolysable triazole-iduronic acid hybrid inhibitors of human α-l-iduronidase: Discovery of enzyme stabilizers for the potential treatment of MPSI

Preparation of substituent-diverse, triazole-iduronic acid hybrid molecules by click reaction of an azido iduronic acid derivative with randomly chosen alkynes is described. Library members were screened for their ability to inhibit α-l-iduronidase, and hit molecules and analogues were then investigated for their ability to stabilize rh-α-IDUA in a thermal denaturation study. This work resulted in the discovery of the first small molecules that can be used to stabilize exogenous rh-α-IDUA protein in vitro.