5-Ethyl-1-beta-D-glucopyranosyl-5-phenyl-2,4,6(1H,3H,5H)-pyrimidinetrione

Base Information

• Chemical Name: 5-Ethyl-1-beta-D-glucopyranosyl-5-phenyl-2,4,6(1H,3H,5H)-pyrimidinetrione
• CAS No.: 72209-10-0
• Molecular Formula: C₁₈H₂₂N₂O₈
• Molecular Weight: 394.381
• Nikkaji Number: J599.430F
• ChEMBL ID: CHEMBL3706521
• Mol file: 72209-10-0.mol

Synonyms:1-(beta-D-glucopyranosyl)phenobarbital;1-GPPB;5-ethyl-1-(1-beta-glucopyranosyl)-5-phenyl-2,4,6-(1H,3H,5H)pyrimidinetrione;phenobarbital-N-glucoside

Chemical Property of 5-Ethyl-1-beta-D-glucopyranosyl-5-phenyl-2,4,6(1H,3H,5H)-pyrimidinetrione

Chemical Property:

• PSA: 156.63000
• Density: 1.494g/cm³
• LogP: -1.52060
• XLogP3: -0.7
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 4
• Exact Mass: 394.13761566
• Heavy Atom Count: 28
• Complexity: 637

Purity/Quality:

97% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC1(C(=O)NC(=O)N(C1=O)C2C(C(C(C(O2)CO)O)O)O)C3=CC=CC=C3
• Isomeric SMILES: CCC1(C(=O)NC(=O)N(C1=O)[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)O)C3=CC=CC=C3

Technology Process of 5-Ethyl-1-beta-D-glucopyranosyl-5-phenyl-2,4,6(1H,3H,5H)-pyrimidinetrione

There total 6 articles about 5-Ethyl-1-beta-D-glucopyranosyl-5-phenyl-2,4,6(1H,3H,5H)-pyrimidinetrione 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:

phenobarbital (50-06-6) → 5-ethyl-1-β-D-glucopyranosyl-5-phenyl-2,4,6-(1H,3H,5H)pyrimidinetrione (72209-10-0,121918-10-3,121918-11-4)

Guidance literature:

Multi-step reaction with 2 steps

1: SnCl₄ / 1,2-dichloro-ethane / 0 °C

2: sodium methoxide / methanol

With sodium methylate; tin(IV) chloride; In methanol; 1,2-dichloro-ethane;

DOI:10.1016/0008-6215(89)85110-9

Reference yield:

phenobarbital (50-06-6) → 5-ethyl-1-β-D-glucopyranosyl-5-phenyl-2,4,6-(1H,3H,5H)pyrimidinetrione (72209-10-0,121918-10-3,121918-11-4)

Guidance literature:

Multi-step reaction with 2 steps

1: SnCl₄ / 1,2-dichloro-ethane / 0 °C

2: sodium methoxide / methanol

With sodium methylate; tin(IV) chloride; In methanol; 1,2-dichloro-ethane;

DOI:10.1016/0008-6215(89)85110-9

Reference yield:

β-D-glucose pentaacetate (604-69-3) → 5-ethyl-1-β-D-glucopyranosyl-5-phenyl-2,4,6-(1H,3H,5H)pyrimidinetrione (72209-10-0,121918-10-3,121918-11-4)

Guidance literature:

Multi-step reaction with 2 steps

1: SnCl₄ / 1,2-dichloro-ethane / 0 °C

2: sodium methoxide / methanol

With sodium methylate; tin(IV) chloride; In methanol; 1,2-dichloro-ethane;

DOI:10.1016/0008-6215(89)85110-9

upstream raw materials:

5-ethyl-5-phenyl-1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-2,4,6(1H,3H,5H)pyrimidinetrione

phenobarbital

β-D-glucose pentaacetate

Downstream raw materials:

5-ethyl-1-β-D-glucopyranosyl-3-methyl-5-phenyl-2,4,6-(1H,3H,5H)pyrimidinetrione

5-ethyl-1-β-D-glucopyranosyl-3-methyl-5-phenyl-2,4,6-(1H,3H,5H)pyrimidinetrione

Refernces