5-Phenylethynyl-2'-deoxyuridine

Base Information

• Chemical Name: 5-Phenylethynyl-2'-deoxyuridine
• CAS No.: 77887-20-8
• Molecular Formula: C17H16 N2 O5
• Molecular Weight: 328.324
• ChEMBL ID: CHEMBL223015
• DSSTox Substance ID: DTXSID20470206
• Nikkaji Number: J569.876F
• Wikidata: Q82298206
• Mol file: 77887-20-8.mol

Synonyms:5-phenylethynyl-2'-deoxyuridine;77887-20-8;1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-(2-phenylethynyl)pyrimidine-2,4-dione;Uridine,2'-deoxy-5-(phenylethynyl)-;5-(3-Phenylethynyl)-dUrd;CHEMBL223015;DTXSID20470206;AG-H-12223;1-(4-Hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-5-phenylethynyl-1H-pyrimidine-2,4-dione;1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]-5-(2-phenylethynyl)pyrimidine-2,4-dione

Chemical Property of 5-Phenylethynyl-2'-deoxyuridine

Chemical Property:

• PKA: 8.25±0.10(Predicted)
• PSA: 104.81000
• Density: 1.49±0.1 g/cm3(Predicted)
• LogP: -0.01060
• XLogP3: 0.5
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 4
• Exact Mass: 328.10592162
• Heavy Atom Count: 24
• Complexity: 611

Purity/Quality:

97% ^*data from raw suppliers

2'-DEOXY-5-(PHENYLETHYNYL)-URIDINE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(C(OC1N2C=C(C(=O)NC2=O)C#CC3=CC=CC=C3)CO)O
• Isomeric SMILES: C1[C@@H]([C@H](O[C@H]1N2C=C(C(=O)NC2=O)C#CC3=CC=CC=C3)CO)O

Technology Process of 5-Phenylethynyl-2'-deoxyuridine

There total 11 articles about 5-Phenylethynyl-2'-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: 88.0%

phenylacetylene (536-74-3) + 5-(Trifluoromethanesulfonyloxy)-2'-deoxyuridine (151361-85-2) → 1-((2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)-tetrahydrofuran-2-yl)-5-(phenylethynyl)pyrimidine-2,4(1H,3H)-dione (77887-20-8) + 3-(2′-deoxy-β-D-ribofuranosyl)-6-(phenyl)-2,3-dihydrofuro-[2,3-d]pyrimidin-2-one (319425-61-1)

Guidance literature:

With copper(l) iodide; triethylamine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In N,N-dimethyl-formamide; at 50 ℃; for 2h;

DOI:10.1021/jo00076a019

Reference yield: 86.0%

C21H20N2O7 (943446-57-9) → 1-((2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)-tetrahydrofuran-2-yl)-5-(phenylethynyl)pyrimidine-2,4(1H,3H)-dione (77887-20-8)

Guidance literature:

With sodium hydroxide; In pyridine; ethanol; at 4 ℃;

DOI:10.1039/b705805e

Reference yield: 71.2%

5-Iodo-2'-deoxyuridine (54-42-2,162239-35-2) + phenylacetylene (536-74-3) → 1-((2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)-tetrahydrofuran-2-yl)-5-(phenylethynyl)pyrimidine-2,4(1H,3H)-dione (77887-20-8)

Guidance literature:

With copper(l) iodide; palladium diacetate; triethylamine; tris(4,6-dimethyl-3-sulfonatophenyl)phosphine trisodium salt hydrate; In water; acetonitrile; at 65 ℃; for 0.5h; Inert atmosphere;

DOI:10.1002/ejoc.201000313

upstream raw materials:

C₃₃H₂₈N₂O₇

5-Phenylethynyl-1-((2R,4S,5R)-4-trimethylsilanyloxy-5-trimethylsilanyloxymethyl-tetrahydro-furan-2-yl)-1H-pyrimidine-2,4-dione

phenylacetylene

5-(Trifluoromethanesulfonyloxy)-2'-deoxyuridine

Downstream raw materials:

3-(2′-deoxy-β-D-ribofuranosyl)-6-(phenyl)-2,3-dihydrofuro-[2,3-d]pyrimidin-2-one

5-phenylethynyl-2'-deoxy-5'-O-(4,4'-dimethoxytrityl)uridine