Licofelone Acyl--D-glucuronide

Base Information

• Chemical Name: Licofelone Acyl--D-glucuronide
• CAS No.: 1033702-58-7
• Molecular Formula: C29H30ClNO8
• Molecular Weight: 556
• Mol file: 1033702-58-7.mol

Synonyms:Licofelone Acyl--D-glucuronide;Licofelone M1 Metabolite;1-[6-(4-Chlorophenyl)-2,3-dihydro-2,2-diMethyl-7-phenyl-1H-pyrrolizine-5-acetate] β-D-Glucopyranuronic Acid;beta-D-Glucopyranuronic acid 1-[6-(4-chlorophenyl)-2,3-dihydro-2,2-dimethyl-7-phenyl-1H-pyrrolizine-5-acetate]

Chemical Property of Licofelone Acyl--D-glucuronide

Chemical Property:

• Boiling Point: 738.4±60.0 °C(Predicted)
• PKA: 2.68±0.70(Predicted)
• PSA: 138.45000
• Density: 1.47±0.1 g/cm3(Predicted)
• LogP: 3.03570

Purity/Quality:

99% ^*data from raw suppliers

LicofeloneAcyl-β-D-glucuronide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: M1 metabolite of Licofeline M1 metabolite of Licofeline.

Technology Process of Licofelone Acyl--D-glucuronide

There total 18 articles about Licofelone Acyl--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:

methyl (benzyl 2,3,4-tri-O-acetyl-β-D-glucopyranosid)uronate (3080-47-5) → Licofelone glucuronide (1033702-58-7)

Guidance literature:

Multi-step reaction with 8 steps

1: MeONa / methanol / 12 h / -40 - 0 °C

2: 4-DMAP, imidazole / dimethylformamide / 48 h / 80 °C

3: aq. NaOH / tetrahydrofuran / 10 h / 50 °C

4: 1.) (EtO)2POCl, Et₃N, 2.) 4-DMAP / 1) toluene, 0 deg C, 1.5 h; 2) rt, 6 h

5: 71 percent / H₂ / Pd/C / ethyl acetate / 48 h / Ambient temperature

6: 72 percent / PPh₃, DIAD / tetrahydrofuran / 2 h / -50 - 20 °C

7: 67 percent / Zn, aq. KH₂PO₄ buffer / 12 h / Ambient temperature

8: aq. HF / acetonitrile / 5 h / 0 - 20 °C

With 1H-imidazole; dmap; sodium hydroxide; KH₂PO₄ buffer; di-isopropyl azodicarboxylate; hydrogen fluoride; hydrogen; sodium methylate; diethyl chlorophosphate; triethylamine; triphenylphosphine; zinc; palladium on activated charcoal; In tetrahydrofuran; methanol; ethyl acetate; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1016/S0960-894X(97)00123-6

Reference yield:

methyl (benzyl 2,3,4-tri-O-acetyl-β-D-glucopyranosid)uronate (3080-47-5) → (2S,3S,4S,5R,6R)-6-{2-[2-(4-Chloro-phenyl)-6,6-dimethyl-1-phenyl-6,7-dihydro-5H-pyrrolizin-3-yl]-acetoxy}-3,4,5-trihydroxy-tetrahydro-pyran-2-carboxylic acid (1033702-58-7)

Guidance literature:

Multi-step reaction with 8 steps

1: MeONa / methanol / 12 h / -40 - 0 °C

2: 4-DMAP, imidazole / dimethylformamide / 48 h / 80 °C

3: aq. NaOH / tetrahydrofuran / 10 h / 50 °C

4: 1.) (EtO)2POCl, Et₃N, 2.) 4-DMAP / 1) toluene, 0 deg C, 1.5 h; 2) rt, 6 h

5: 71 percent / H₂ / Pd/C / ethyl acetate / 48 h / Ambient temperature

6: 72 percent / PPh₃, DIAD / tetrahydrofuran / 2 h / -50 - 20 °C

7: 67 percent / Zn, aq. KH₂PO₄ buffer / 12 h / Ambient temperature

8: aq. HF / acetonitrile / 5 h / 0 - 20 °C

With 1H-imidazole; dmap; sodium hydroxide; KH₂PO₄ buffer; di-isopropyl azodicarboxylate; hydrogen fluoride; hydrogen; sodium methylate; diethyl chlorophosphate; triethylamine; triphenylphosphine; zinc; palladium on activated charcoal; In tetrahydrofuran; methanol; ethyl acetate; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1016/S0960-894X(97)00123-6

Reference yield:

(2S,3R,4S,5R,6R)-6-Benzyloxy-3,4,5-tris-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-carboxylic acid → Licofelone glucuronide (1033702-58-7)

Guidance literature:

Multi-step reaction with 5 steps

1: 1.) (EtO)2POCl, Et₃N, 2.) 4-DMAP / 1) toluene, 0 deg C, 1.5 h; 2) rt, 6 h

2: 71 percent / H₂ / Pd/C / ethyl acetate / 48 h / Ambient temperature

3: 72 percent / PPh₃, DIAD / tetrahydrofuran / 2 h / -50 - 20 °C

4: 67 percent / Zn, aq. KH₂PO₄ buffer / 12 h / Ambient temperature

5: aq. HF / acetonitrile / 5 h / 0 - 20 °C

With dmap; KH₂PO₄ buffer; di-isopropyl azodicarboxylate; hydrogen fluoride; hydrogen; diethyl chlorophosphate; triethylamine; triphenylphosphine; zinc; palladium on activated charcoal; In tetrahydrofuran; ethyl acetate; acetonitrile;

DOI:10.1016/S0960-894X(97)00123-6

upstream raw materials:

O¹-benzyl-β-D-glucopyranuronic acid methyl ester

methyl (benzyl 2,3,4-tri-O-acetyl-β-D-glucopyranosid)uronate

methyl (benzyl 2,3,4-tri-O-tert-butyldimethylsilyl-β-D-glucopyranosid)uronate

2,2,2-trichloroethyl (benzyl 2,3,4-tri-O-tert-butyldimethylsilyl-β-D-glucopyranosid)uronate

Refernces