99409-32-2

Usage

Uses

Used in Pharmaceutical Industry:
Ethyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-b-D-thioglucopyranoside is used as a reactant in the synthesis of Me 2-amino-2-deoxy-a-D-glucopyranoside 6-phosphate and Me 2-amino-2-deoxy-b-D-glucopyranoside 6-phosphate. These synthesized compounds act as cell wall inhibitors targeting the GlmM and GlmU enzymes in Mycobacterium tuberculosis, which are responsible for the biosynthesis of a key component of bacterial cell walls. By inhibiting these enzymes, the compound can potentially contribute to the development of new treatments for tuberculosis.

Upstream product

• 10022-13-6 1,3,4,6-tetra-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranose 
• 75-08-1 ethanethiol 
• 10022-13-6 1,3,4,6-tetra-O-acetyl-2-phthalimido-2-deoxy-α-D-glucopyranose 
• 10022-13-6 1,3,4,6-tetra-O-acetyl-2-deoxy-2-phthalimido-D-glucopyranose 
• 31505-45-0 2-deoxy-2-phthalimido-D-glucopyranose 
• 108-24-7 acetic anhydride 
• 63000-70-4 C₂₀H₂₀INO₉ 
• 75-03-6 ethyl iodide 
• 85-44-9 phthalic anhydride 
• 90-76-6 2-deoxy-2-amino glucose 
• 72858-55-0 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-D-glucopyranose 
• 31505-42-7 2-(2-carboxybenzamido)-2-deoxy-D-glucopyranose 
• 138906-41-9 4-methoxylphenzyl 2-deoxy-2-phthalimido-3,4,6-tri-O-acetyl-β-D-glucopyranoside 
• 17460-45-6 tetra-acetyl glucosamine 

Downstream Products

• 130674-85-0 Acetic acid (2R,3S,4R,5R,6S)-3-acetoxy-2-acetoxymethyl-6-((2R,3R,4R,5S,6S)-3,5-bis-benzyloxy-2-methoxy-6-methyl-tetrahydro-pyran-4-yloxy)-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-tetrahydro-pyran-4-yl ester 
• 129519-28-4 2-((6S,7R,8aS)-6-ethylsulfanyl-8-hydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl)-isoindole-1,3-dione 
• 118579-75-2 methyl 2-O-benzyl-4,6-O-benzylidene-3-O-(3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-α-D-glucopyranoside 
• 104707-08-6 1,2,3,4-tetra-O-benzoyl-6-O-(3,4-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-β-D-glucopyranose 
• 140686-53-9 p-nitrophenyl 2-azido-3-O-benzyl-6-O-tert-butyldimethylsilyl-2-deoxy-4-O-(3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-β-D-mannopyranoside 
• 130539-43-4 ethyl 2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside 
• 131643-27-1 C₄₁H₄₁NO₁₇ 
• 165061-00-7 allyl 3-O-benzyl-2,6-bis-O-(3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-α-D-mannopyranoside 
• 10022-13-6 1,3,4,6-tetra-O-acetyl-2-deoxy-2-phthalimido-D-glucopyranose 
• 115533-35-2 ethyl 3,6-di-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside 
• 129519-27-3 2-((6S,7R,8aS)-8-benzyloxy-6-ethylsulfanyl-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl)-isoindole-1,3-dione 

Relevant academic research and scientific papers

ANTIMICROBIAL VACCINE COMPOSITIONS

This invention is directed to antimicrobial vaccine compounds and compositions comprising oligosaccharide β-(1→6)- glucosamine groups having from 3 to 12 glucosamine units linked through a linker group to tetanus toxoid wherein the toxoid is primarily in

LOW CONTAMINANT ANTIMICROBIAL VACCINES

Disclosed are antimicrobial vaccines comprising oligosaccharide β-(1→6)-glucosamine groups.

METHODS FOR PROVIDING CONTINUOUS THERAPY AGAINST PNAG COMPRISING MICROBES

Disclosed are antimicrobial vaccines comprising oligosaccharide β-(1→6)-glucosamine groups.

Methods for inhibiting biofilm formation

Disclosed are methods and kits of parts useful in inhibiting biofilm formation in vivo in subjects at risk of developing biofilms. These methods include inhibiting biofilm formation where the extracellular matrix in the biofilm includes poly-β-(1→6)glucos

Chemoenzymatic Synthesis of Glycoconjugates Mediated by Regioselective Enzymatic Hydrolysis of Acetylated 2-Amino Pyranose Derivatives

Highly regioselective deprotection of a series of 2-amino pyranose building blocks was achieved by enzymatic hydrolysis. These monodeprotected intermediates were successfully used in the synthesis of a variety of glycoconjugate derivatives with a core of glucosamine or galactosamine, including neo-glycoproteins and glycosphingolipids. The hydrolysis catalyzed by acetylxylan esterase from Bacillus pumilus (AXE) is suitable for the synthesis of neo-glycoproteins with an N-acetyl glucosamine core. The hydrolysis catalyzed by Candida rugosa lipase (CRL) was successfully applied in the preparation of new sialylated glycolipids starting from glucosamine building blocks protected as phthalimide. This chemoenzymatic approach can be used for the preparation of new glycoconjugate products with anticancer activity.

Triflic acid-mediated synthesis of thioglycosides

An efficient synthesis of thioglycosides from per-acetates in the presence of triflic acid is described. The developed protocol features high reaction rates and product yields. Some reactive sugar series give high efficiency in the presence of sub-stoichiometric trifluoromethanesulfonic acid (TfOH) in contrast to other known protocols that require multiple equivalents of Lewis acids to reach high conversion rates.

Ionic-liquid supported rapid synthesis of an: N -glycan core pentasaccharide on a 10 g scale

A new and efficient Ionic Liquid-Supported Oligosaccharide Synthesis (ILSOS) strategy for an N-linked core pentasaccharide on a 10 g scale is reported. This new ILSOS includes a new spacer for an IL support, a new tagging strategy, and fast, efficient and orthogonal removal of the ionic-liquid support, producing the N-linked core pentasaccharide with direct applicability potential in a short time, with high yield and on a large gram scale.

Synthesis of Azido-Glycans for Chemical Glycomodification of Proteins

Chemically produced, accurately linkable oligosaccharides are of importance for the synthesis of neo-glycoproteins. On the route to high-mannose type N-glycans, we present a convenient synthesis of several glycans bearing an azide moiety at the reducing end. An azido-glycan core structure as valuable precursor was modified into the protected N-glycan pentasaccharide core structure and the possibility of modular attachment of different antenna was demonstrated through synthesis of a pentamannose donor and glycosylation with the core structure. The azido function allows for chemical ligation with recombinantly modified proteins featuring noncanonical cyclooctyne amino acids, providing access to customized glycopatterns of glycoproteins, e.g., of antibodies that are of high interest for biopharmaceutical applications.

Synthesis and immunological evaluation of a low molecular weight saccharide with TLR-4 agonist activity

The paucity of FDA approved adjuvants renders the synthesis, characterization, and use of new compounds as vaccine adjuvants, a necessity. For this purpose, a novel saccharide analog has been synthesized from glucosamine, pyruvylated galactose and 1,4-cyclohexanediol and its biological efficacy was determined in innate immune cells. More specifically, we assessed the production of pro-inflammatory cytokines from the murine monocyte cell line, Raw 264.7 and from C57 BL/6 mouse peritoneal macrophages following exposure to the saccharide analog. Our data conclude that the novel saccharide has immunostimulatory activity on mouse macrophages as indicated by the elevated levels of IL-6 and TNF-α in culture supernatants. This effect was TLR-4-dependent but TLR-2-independent. Our data, suggest TLR-4 agonism; a key feature of vaccine adjuvants.

Synthesis of building blocks for an iterative approach towards oligomers of the Streptococcus pneumoniae type 1 zwitterionic capsular polysaccharide repeating unit

Zwitterionic capsular polysaccharide extracts, 8 kDa in mass, from Streptococcus pneumoniae type 1 (Spt1) have shown unique T-cell activating properties. Oligomers of the trisaccharide repeating unit of the Spt1 capsular polysaccharide [3)-4-NH2-α-d-QuipNAc-(14)-α-d-GalpA-(13)-α-d-GalpA-(1-]n of defined length are needed to further investigate this response. An approach towards iteratively extendable trisaccharide building blocks of the zwitterionic capsular polysaccharides of Spt1 is described. Key elements include the comparison of pre-glycosylation oxidation and post-glycosylation oxidation approaches using thioglycoside donors to the target trisaccharide, the optimisation of the post-glycosylation oxidation approach, and the conversion of the trisaccharide to building blocks tailored for iterative glycosylation. The construction and evaluation of stereotunable 2-N-3-O-oxazolidinone donors for the common bacterial 2-acetamido-4-amino-2,4,6-trideoxy-α-d-galactopyranoside motif is also described, as is a key intermediate for their efficient synthesis.