[(2S,5R)-5-(2,4-Dioxo-3,4-dihydropyrimidin-1(2H)-yl)oxolan-2-yl]methyl benzoate

Base Information

• Chemical Name: [(2S,5R)-5-(2,4-Dioxo-3,4-dihydropyrimidin-1(2H)-yl)oxolan-2-yl]methyl benzoate
• CAS No.: 28616-91-3
• Molecular Formula: C16H16N2O5
• Molecular Weight: 316.313
• ChEMBL ID: CHEMBL88993
• DSSTox Substance ID: DTXSID10558764
• Mol file: 28616-91-3.mol

Synonyms:CHEMBL88993;28616-91-3;SCHEMBL10465192;DTXSID10558764;PBFATPYEUBCWJS-GXTWGEPZSA-N;BDBM50013116;5'-O-benzoyl-2',3'-dideoxy-uridine;[(2S,5R)-5-(2,4-Dioxo-3,4-dihydropyrimidin-1(2H)-yl)oxolan-2-yl]methyl benzoate;Benzoic acid 5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester (ddUrd)

Chemical Property of [(2S,5R)-5-(2,4-Dioxo-3,4-dihydropyrimidin-1(2H)-yl)oxolan-2-yl]methyl benzoate

Chemical Property:

• XLogP3: 1.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 5
• Exact Mass: 316.10592162
• Heavy Atom Count: 23
• Complexity: 513

Purity/Quality:

97% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1CC(OC1COC(=O)C2=CC=CC=C2)N3C=CC(=O)NC3=O
• Isomeric SMILES: C1C[C@@H](O[C@@H]1COC(=O)C2=CC=CC=C2)N3C=CC(=O)NC3=O

Technology Process of [(2S,5R)-5-(2,4-Dioxo-3,4-dihydropyrimidin-1(2H)-yl)oxolan-2-yl]methyl benzoate

There total 19 articles about [(2S,5R)-5-(2,4-Dioxo-3,4-dihydropyrimidin-1(2H)-yl)oxolan-2-yl]methyl benzoate 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: 85.0%

benzoyl chloride (98-88-4) + 2',3'-Dideoxyuridine (5983-09-5,153547-98-9) → 1-(5-O-benzoyl-2,3-dideoxy-β-D-glycero-pentofuranosyl)uracil (28616-91-3)

Guidance literature:

With pyridine; In N,N-dimethyl-formamide;

DOI:10.1081/NCN-100002484

Reference yield: 85.0%

tribenzoyl uridine (1748-04-5) → 1-(5-O-benzoyl-2,3-dideoxy-β-D-glycero-pentofuranosyl)uracil (28616-91-3)

Guidance literature:

With magnesium(II) perchlorate; N-methylcarbazole; In water; isopropyl alcohol; for 18h; Irradiation;

DOI:10.1021/ja00271a057

Reference yield: 75.0%

1-(5-O-benzoyl-2,3-dideoxy-β-D-glycero-pento-2-enofuranosyl)uracil (6038-56-8) → 1-(5-O-benzoyl-2,3-dideoxy-β-D-glycero-pentofuranosyl)uracil (28616-91-3)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethanol; for 2h; under 1292.9 Torr;

DOI:10.1021/jm00163a043

upstream raw materials:

Benzoic acid (2S,5R)-5-[3-((E)-3-ethoxy-acryloyl)-ureido]-tetrahydro-furan-2-ylmethyl ester

1-(5-O-benzoyl-2,3-dideoxy-β-D-glycero-pento-2-enofuranosyl)uracil

tribenzoyl uridine

1-chloro-5-O-benzoyl-2,3-dideoxy-D-glycero-pentofuranose

Downstream raw materials:

Benzoic acid (2S,5R)-5-(4-methoxy-2-oxo-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester

5'-O-benzoyl-2',3'-dideoxy-4-thiouridine

Benzoic acid (2S,5R)-5-(5-chloro-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester

2',3'-Dideoxyuridine