((2R,3S,5R)-3-Acetoxy-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-2-yl)methyl acetate

Base Information

• Chemical Name: ((2R,3S,5R)-3-Acetoxy-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-2-yl)methyl acetate
• CAS No.: 13030-62-1
• Molecular Formula: C13H16 N2 O7
• Molecular Weight: 312.279
• DSSTox Substance ID: DTXSID60427739
• Nikkaji Number: J211.542E
• Wikidata: Q82240422
• Mol file: 13030-62-1.mol

Synonyms:13030-62-1;3',5'-Di-O-acetyl-2'-deoxyuridine;((2R,3S,5R)-3-Acetoxy-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-2-yl)methyl acetate;[(2R,3S,5R)-3-acetyloxy-5-(2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methyl acetate;SCHEMBL1271663;DTXSID60427739;XCLQOCSQUSRPDH-HOSYDEDBSA-N;AKOS024260289;3'-O,5'-O-Diacetyl-2'-deoxyuridine;AC-32266;3',5'-Di-O-acetyl-2'-deoxy-D-uridine;3/',5/'-Di-O-acetyl-2/'-deoxyuridine;E87794;A888774;J-700302;((2R,3S,5R)-3-Acetoxy-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-2-yl)methylacetate;[(2R,3S,5R)-3-(acetyloxy)-5-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)oxolan-2-yl]methyl acetate

Chemical Property of ((2R,3S,5R)-3-Acetoxy-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-2-yl)methyl acetate

Chemical Property:

• Melting Point: 99-101°C
• PSA: 157.15000
• Density: 1.4g/cm3
• LogP: -0.41810
• Storage Temp.: Refrigerator
• Solubility.: Chloroform (Slightly), Ethyl Acetate (Slightly), Water (Slightly)
• XLogP3: -0.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 6
• Exact Mass: 312.09575085
• Heavy Atom Count: 22
• Complexity: 531

Purity/Quality:

97% ^*data from raw suppliers

3'',5''-Di-O-acetyl-2''-deoxyuridine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)OCC1C(CC(O1)N2C=CC(=O)NC2=O)OC(=O)C
• Isomeric SMILES: CC(=O)OC[C@@H]1[C@H](C[C@@H](O1)N2C=CC(=O)NC2=O)OC(=O)C
• Uses: An antitumor carbocyclic nucleoside An antitumor carbocyclic nucleoside.

Technology Process of ((2R,3S,5R)-3-Acetoxy-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-2-yl)methyl acetate

There total 10 articles about ((2R,3S,5R)-3-Acetoxy-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-2-yl)methyl acetate 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: 100.0%

2'-deoxyuridine (951-78-0,63844-76-8) + acetic anhydride (108-24-7) → 3',5'-di-O-acetyl-2'-deoxyuridine (13030-62-1)

Guidance literature:

With dmap;

DOI:10.1021/jo9822939

Reference yield: 96.0%

acetic anhydride (108-24-7) + 3'-O-acetyl-2'-deoxyuridine (23197-88-8) → 3',5'-di-O-acetyl-2'-deoxyuridine (13030-62-1)

Guidance literature:

With O-(3-sulfopropyl)-functionalized nano γ-Al₂O₃; In neat (no solvent); at 20 - 50 ℃; for 0.5h;

DOI:10.1016/j.carres.2012.10.014

Reference yield: 95.0%

1-(3,5-di-O-acetyl-2-bromo-2-deoxy-β-D-ribofuranosyl)-uracil (19325-92-9) → 3',5'-di-O-acetyl-2'-deoxyuridine (13030-62-1)

Guidance literature:

With sodium tetrahydroborate; tributyltin chloride; In ethanol; for 0.333333h; Heating;

upstream raw materials:

2'-deoxyuridine

acetic anhydride

4-<(triphenylmethyl)oxy>-1-butyne

3',5'-O-diacetyl-5-iodo-2'-deoxyuridine

Downstream raw materials:

1-(2'-deoxy-3',5'-tri-O-acetyl-β-D-ribofuranosyl)-5-fluorouracil

1-(3,5-di-O-acetyl-β-D-2-deoxyribofuranosyl)-5-bromouracil

1-(3,5-di-O-acetyl-β-D-2-deoxyribofuranosyl)-5-chlorouracil

3',5'-O-diacetyl-5-iodo-2'-deoxyuridine

Refernces

• 1、 Haga,Ishikawa,Takayanagi,Ogura. "Photocycloaddition of deoxyuridines to 2,3-dimethyl-2-butene". . p. 728 - 737. Retrieved 1994.
• 2、 Talekar,Coe,Walker. "An efficient and general synthesis of 5'-esters of 2',3'-didehydro-2',3'-dideoxynucleosides: A facile opening of 2',3'-orthoacetates of ribonucleosides followed by reductive elimination of the halogenoacetates". . p. 303 - 306. Retrieved 1993.
• 3、 Tauraite, Daiva,Jakubovska, Jevgenija,Dabu?inskaite, Julija,Bratchikov, Maksim,Me?kys, Rolandas. "Modified nucleotides as substrates of terminal deoxynucleotidyl transferase". . . Retrieved 2017.
• 4、 Lin,Gao. "Synthesis and biological activity of 5-(trifluoromethyl)- and 5-(pentafluorethyl)pyrimidine nucleoside analogues". . p. 598 - 601. Retrieved 1983.
• 5、 Bayach, Imene,Khalil, Ahmed,Mathé, Christophe. "A synergistic synthetic and computational insights towards anomerization of N-nitro pyrimidine nucleosides using fluorinating agents". . . Retrieved 2020.