(R)-Naproxen Acyl-b-D-glucuronide

Base Information

• Chemical Name: (R)-Naproxen Acyl-b-D-glucuronide
• CAS No.: 112828-15-6
• Molecular Formula: C₂₀H₂₂O₉
• Molecular Weight: 406.389
• Hs Code.: 29389090
• Mol file: 112828-15-6.mol

Synonyms:b-D-Glucopyranuronic acid,1-(6-methoxy-a-methyl-2-naphthaleneacetate),(R)-; (R)-Naproxen glucuronide

Chemical Property of (R)-Naproxen Acyl-b-D-glucuronide

Chemical Property:

• Melting Point: 128-130°C
• Refractive Index: 1.652
• PSA: 142.75000
• LogP: 0.38730
• Storage Temp.: Hygroscopic, -20°C Freezer, Under Inert Atmosphere
• Solubility.: Methanol (Slightly)

Purity/Quality:

98% ^*data from raw suppliers

(R)-NaproxenAcyl-β-D-glucuronide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: A metabolite of Naproxen A metabolite of Naproxen.

Technology Process of (R)-Naproxen Acyl-b-D-glucuronide

There total 8 articles about (R)-Naproxen Acyl-b-D-glucuronide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

C27H28O9 (946517-36-8) → (+)-Naproxen glucuronide (41945-43-1,112828-15-6)

Guidance literature:

With cyclohexa-1,4-diene; palladium on activated charcoal; In tetrahydrofuran; isopropyl alcohol; for 2h; Heating;

DOI:10.1016/j.tet.2007.05.050

Reference yield: 99.0%

benzyl 1-O-[(S)-2-(6-methoxy-2-naphthyl)propionyl]-2,3,4-tri-O-benzyl-β-D-glucopyranuronate → (+)-Naproxen glucuronide (41945-43-1,112828-15-6)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethyl acetate; at 20 ℃; under 760 Torr;

DOI:10.1081/CAR-120034003

Reference yield:

(2S)-2-(6-methoxy(2-naphthyl))propanoic acid (22204-53-1) → (+)-Naproxen glucuronide (41945-43-1,112828-15-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 67 percent / HATU; N-methylmorpholine / acetonitrile / 20 °C

2: 100 percent / cyclohexa-1,4-diene / Pd-C / tetrahydrofuran; propan-2-ol / 2 h / Heating

With 4-methyl-morpholine; cyclohexa-1,4-diene; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; palladium on activated charcoal; In tetrahydrofuran; isopropyl alcohol; acetonitrile;

DOI:10.1016/j.tet.2007.05.050

upstream raw materials:

(R)-2-(6-methoxy-2-naphthyl)propionic acid

uridine diphosphoglucuronic acid

C₂₇H₂₈O₉

(2S)-2-(6-methoxy(2-naphthyl))propanoic acid

Refernces

• 1、 Bischer, Alfred,Zia-Amirhosseini, Parnian,Iwaki, Masahiro,McDonagh, Antony F.,Benet, Leslie Z.. "Stereoselective Binding Properties of Naproxen Glucuronide Diastereomers to Proteins". . p. 379 - 396. Retrieved 1995.
• 2、 Baba, Akiko,Yoshioka, Tadao. "Synthesis of 1-β-O-acyl glucuronides of diclofenac, mefenamic acid and (S)-naproxen by the chemo-selective enzymatic removal of protecting groups from the corresponding methyl acetyl derivatives". . p. 3303 - 3310. Retrieved 2008/09/17.