228412-71-3

Basic information

• Product Name: β-D-Glucopyranuronic Acid Methyl Ester 2,3,4-Triacetate 1-(4-Nitrophenyl Carbonate)
• Synonyms: [Methyl(2,3,4-tri-O-acetyl-β-D-glucopyranosyl)uronate]-4-nitro-phenyl Carbonate;β-D-Glucopyranuronic Acid Methyl Ester 2,3,4-Triacetate 1-(4-Nitrophenyl Carbonate);UOZDLZHZVWFBBG-UHFFFAOYSA-N
• CAS NO: 228412-71-3
• Molecular Formula: C₂₀H₂₁NO₁₄
• Molecular Weight: 499.37904
• Product Categories: Glucuronides, Intermediates;Glucuronides;Intermediates
• Mol File: 228412-71-3.mol

Chemical Properties

• Appearance: /
• Solubility: Chloroform, Dichloromethane, Ethyl Acetate
• CAS DataBase Reference: β-D-Glucopyranuronic Acid Methyl Ester 2,3,4-Triacetate 1-(4-Nitrophenyl Carbonate)(CAS DataBase Reference)
• NIST Chemistry Reference: β-D-Glucopyranuronic Acid Methyl Ester 2,3,4-Triacetate 1-(4-Nitrophenyl Carbonate)(228412-71-3)
• EPA Substance Registry System: β-D-Glucopyranuronic Acid Methyl Ester 2,3,4-Triacetate 1-(4-Nitrophenyl Carbonate)(228412-71-3)

Safety Data

• Hazardous Substances Data: 228412-71-3(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Synthesis:
β-D-Glucopyranuronic Acid Methyl Ester 2,3,4-Triacetate 1-(4-Nitrophenyl Carbonate) is used as an intermediate in the synthesis of Varenicline Carbamoyl metabolite, a drug used for smoking cessation and as a treatment for nicotine addiction.
Used in Organic Chemistry:
β-D-Glucopyranuronic Acid Methyl Ester 2,3,4-Triacetate 1-(4-Nitrophenyl Carbonate) is used as a protected form of Glucopyranuronic Acid, allowing for the addition of this functional group to other molecules without unwanted side reactions. This is particularly useful in the synthesis of complex organic compounds and pharmaceuticals.

Upstream product

• 3082-95-9 2,3,4-Tri-O-acetyl-β-D-glucopyranuronic acid methylester 
• 7693-46-1 4-Nitrophenyl chloroformate 
• 5070-13-3 bis-(p-nitrophenyl) carbonate 
• 1033-26-7 4,4'-dinitrobenzophenone 
• 7355-18-2 (2S,3S,4S,5R,6S)-3,4,5,6-Tetraacetoxy-tetrahydro-pyran-2-carboxylic acid methyl ester 
• 21085-72-3 1-bromo-2,3,4-tri-O-acetyl-α-D-glucuronic acid methyl ester 
• 3080-47-5 methyl (benzyl 2,3,4-tri-O-acetyl-β-D-glucopyranosid)uronate 
• 72692-06-9 methyl 2,3,4-tri-O-acetyl-D-glucopyranuronate 

Relevant articles and documents

Mirabegron metabolite synthesis method

The invention discloses a mirabegron metabolite synthesis method and belongs to the field of drug metabolism. The mirabegron metabolite synthesis method can prepare a mirabegron metabolite from glucurolactone (1R)-2-2[2-(4-nitrophenyl)ethylamino]-1-phenylethanol as starting materials through eight-step reaction. The mirabegron metabolite synthesis method has the advantages that the synthesis method is reasonable in process design and strong in operability on the basis of optimal preparation steps and reaction conditions screened by a great number of experiments; the synthesis method is high inyield and can reach high chemical purity above 99% and therefore can be applied to industrial production of mirabegron metabolite; the mirabegron metabolite can provide a standard substance for metabolic mechanism research of the mirabegron drug, can be used for exploring the metabolic process of the drugs in vivo, and has high application research value in clinical pharmacokinetic study.

GLUCURONIDE PRODRUGS OF TOFACITINIB

The invention relates to glucuronide prodrug compounds of the Janus kinase (JAK) inhibitor tofacitinib having formula (I): (Formula (I)) where A1 and R1 are as defined. The invention also relates to pharmaceutical compositions comprising such compounds; methods of using such compounds to treat gastrointestinal inflammatory diseases; and processes and intermediates for preparing such compounds.

GLUCURONIDE PRODRUGS OF JANUS KINASE INHIBITORS

The invention relates to glucuronide prodrug compounds of Janus kinase (JAK) inhibitors having formula I: where W1, R1 and A1 are as defined. The invention also relates to pharmaceutical compositions comprising such compounds; methods of using such compounds to treat gastrointestinal inflammatory diseases; and processes and intermediates for preparing such compounds.

Combatting implant-associated biofilms through localized drug synthesis

Bacterial contamination of implantable biomaterials is a significant socioeconomic and healthcare burden. Indeed, bacterial colonization of implants after surgery has a high rate of incidence whereas concurrent prophylaxis using systemic antibiotics has limited clinical success. In this work, we develop enzyme-prodrug therapy (EPT) to prevent and to treat bacteria at interfaces. Towards the overall goal, novel prodrugs for fluoroquinolone antibiotics were developed on a privileged glucuronide scaffold. Whereas carbamoyl prodrugs were not stable and not suitable for EPT, glucuronides containing self-immolative linker between glucuronic acid masking group and the antibiotic were stable in solution and readily underwent bioconversion in the presence of β-glucuronidase. Surface coatings for model biomaterials were engineered using sequential polymer deposition technique. Resulting coatings afforded fast prodrug conversion and mediated antibacterial measures against planktonic species as evidenced by pronounced zone of bacterial growth inhibition around the biomaterial surface. These biomaterials coupled with the glucuronide prodrugs also effectively combatted bacteria within established biofilms and also successfully prevented bacterial colonization of the surface. To our knowledge, this is the first report of EPT engineered to the surface of biomaterials to mediate antibacterial measures.

Reagents for stereoselective preparation of N-carbamyl β-d- glucuronides

Carbamyl glucuronidation is an increasingly well-recognized route of metabolism for secondary amine drugs. Proper characterization of these metabolites requires the synthesis of authentic standards. O-Protected glucuronyl p-nitrophenyl carbonates can be p

Synthesis of self-immolative glucuroenide spacers based on aminomethylcarbamate. Application to 5-fluorouracil prodrugs for antibody-directed enzyme prodrug therapy

The synthesis of three novel potential glucuronide-based prodrugs for antibody-directed enzyme prodrug therapy (ADEPT) is described. These prodrugs were designed to be activated at the tumour site by -glucuronidase to afford the corrresponding anticancer agent, 5-FU. The structural pattern of these compounds includes a self-immolative spacer between the glucuronyl residue and the N1 of 5-FU. Three types of spacers have been elaborated which, after enzymic hydrolysis, spontaneously decompose to deliver an unstable N1 aminal 5-FU derivative and, from there, the cytotoxic drug. All potential prodrugs were stable and proved to be excellent substrates of E. coll in in vitro experiments.