(beta-D-glucopyranosyloxymethyl)deoxyuridine

Base Information

• Chemical Name: (beta-D-glucopyranosyloxymethyl)deoxyuridine
• CAS No.: 53910-96-6
• Molecular Formula: C₁₆H₂₄N₂O₁₁
• Molecular Weight: 420.373
• Nikkaji Number: J996.655B
• Wikidata: Q27191230
• Mol file: 53910-96-6.mol

Synonyms:(beta-D-glucopyranosyloxymethyl)deoxyuridine;alpha-(beta-D-Glucopyranosyloxy)thymidine;beta-D-glucosyl-HOMedU;CHEBI:111513;5-((Glucopyranosyloxy)methyl)uridine;(beta-D-glucosyloxymethyl)deoxyuridine;5-(beta-D-glucopyranosyloxymethyl)-2'-deoxyuridine;2'-deoxy-5-[(beta-D-glucopyranosyloxy)methyl]uridine;Q27191230;1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]pyrimidine-2,4-dione;dJ

Chemical Property of (beta-D-glucopyranosyloxymethyl)deoxyuridine

Chemical Property:

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• PSA: 203.93000
• Density: 1.71g/cm³
• LogP: -4.50620
• XLogP3: -4
• Hydrogen Bond Donor Count: 7
• Hydrogen Bond Acceptor Count: 11
• Rotatable Bond Count: 6
• Exact Mass: 420.13800959
• Heavy Atom Count: 29
• Complexity: 659

Purity/Quality:

97% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(C(OC1N2C=C(C(=O)NC2=O)COC3C(C(C(C(O3)CO)O)O)O)CO)O
• Isomeric SMILES: C1[C@@H]([C@H](O[C@H]1N2C=C(C(=O)NC2=O)CO[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)CO)O

Technology Process of (beta-D-glucopyranosyloxymethyl)deoxyuridine

There total 16 articles about (beta-D-glucopyranosyloxymethyl)deoxyuridine 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: 91.0%

5-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)oxymethyl-2'-deoxyuridine (157728-65-9) → 5-(β-D-glucopyranosyloxymethyl)-2'-deoxyuridine (53910-96-6)

Guidance literature:

With potassium tert-butylate; In methanol; for 16h;

DOI:10.1002/recl.19941130607

Reference yield:

2'-deoxy-5-(hydroxymethyl)uridine (5116-24-5,15425-01-1,143156-50-7) → 5-(β-D-glucopyranosyloxymethyl)-2'-deoxyuridine (53910-96-6)

Guidance literature:

Multi-step reaction with 6 steps

1: 84 percent / CF₃COOH / Heating

2: 90 percent / pyridine / 0.5 h

3: 65 percent / K₂CO₃ / methanol

4: 50 percent / HgBr₂; Hg(CN)2; powdered molecular sieves, 4 Angstroem / acetonitrile / 3 h

5: 78 percent / Et₃N*3HF / pyridine / 16 h

6: 91 percent / KOtBu; methanol / 16 h

With methanol; molecular sieve; 4 A molecular sieve; potassium tert-butylate; mercury(II) cyanide; potassium carbonate; triethylamine tris(hydrogen fluoride); trifluoroacetic acid; mercury dibromide; In pyridine; methanol; acetonitrile; 1: Acetylation / 2: silylation, bifunctional / 3: Deacetylation / 4: Condensation / 5: desilylation / 6: Hydrolysis;

Reference yield:

5-acetoxymethyl-2’-deoxyuridine (148380-55-6) → 5-(β-D-glucopyranosyloxymethyl)-2'-deoxyuridine (53910-96-6)

Guidance literature:

Multi-step reaction with 5 steps

1: 90 percent / pyridine / 0.5 h

2: 65 percent / K₂CO₃ / methanol

3: 50 percent / HgBr₂; Hg(CN)2; powdered molecular sieves, 4 Angstroem / acetonitrile / 3 h

4: 78 percent / Et₃N*3HF / pyridine / 16 h

5: 91 percent / KOtBu; methanol / 16 h

With methanol; molecular sieve; 4 A molecular sieve; potassium tert-butylate; mercury(II) cyanide; potassium carbonate; triethylamine tris(hydrogen fluoride); mercury dibromide; In pyridine; methanol; acetonitrile; 1: silylation, bifunctional / 2: Deacetylation / 3: Condensation / 4: desilylation / 5: Hydrolysis;

upstream raw materials:

5-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)oxymethyl-2'-deoxyuridine

5-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)oxymethyl-2'-deoxy-N³-pivaloyloxymethyluridine

2'-deoxy-5-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)oxymethyluridine

2'-deoxy-5-(2,3,4,6-tetra-O-methoxyacetyl-β-D-glucopyranosyl)oxymethyluridine

Downstream raw materials:

5-(aminomethyl)-2'-deoxyuridine