2',2'-Difluorodeoxyuridine

Base Information

• Chemical Name: 2',2'-Difluorodeoxyuridine
• CAS No.: 114248-23-6
• Molecular Formula: C9H10 F2 N2 O5
• Molecular Weight: 264.186
• Hs Code.: 29389090
• European Community (EC) Number: 806-458-5
• UNII: Y30D8SIL1I
• DSSTox Substance ID: DTXSID50891460
• Nikkaji Number: J465.930I
• Wikidata: Q27294196
• ChEMBL ID: CHEMBL3526970
• Mol file: 114248-23-6.mol

Synonyms:2',2'-dFdU;2',2'-difluoro-2'-deoxyuridine;2',2'-difluorodeoxyuridine

Chemical Property of 2',2'-Difluorodeoxyuridine

Chemical Property:

• Melting Point: 147-149掳C
• PKA: 9.39±0.10(Predicted)
• PSA: 104.55000
• Density: 1.69±0.1 g/cm3(Predicted)
• LogP: -1.57750
• Storage Temp.: -20°C Freezer
• Solubility.: Methanol (Slightly), Water (Very Slightly, Heated)
• XLogP3: -1.3
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 2
• Exact Mass: 264.05577775
• Heavy Atom Count: 18
• Complexity: 414

Purity/Quality:

97% ^*data from raw suppliers

2’,2’-Difluoro-2’-deoxyuridine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CN(C(=O)NC1=O)C2C(C(C(O2)CO)O)(F)F
• Isomeric SMILES: C1=CN(C(=O)NC1=O)[C@H]2C([C@@H]([C@H](O2)CO)O)(F)F
• Uses: A metabolite product of Gemcitabine A metabolite of Gemcitabine (G305000) in human plasma.

Technology Process of 2',2'-Difluorodeoxyuridine

There total 7 articles about 2',2'-Difluorodeoxyuridine 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: 99.0%

((2R,3R,5R)-3-(benzoyloxy)-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-4,4-difluorotetrahydrofuran-2-yl)methyl benzoate (143157-27-1) → Deoxydifluorouridine (114248-23-6)

Guidance literature:

With ammonia; In methanol; at 20 ℃; for 12h; Temperature;

Reference yield: 95.0%

gemcitabine hydrochloride (122111-03-9) → Deoxydifluorouridine (114248-23-6)

Guidance literature:

With acetic acid; sodium nitrite; In water; at 20 ℃; for 48h;

Reference yield: 90.0%

2'-deoxy-2',2'-difluorouridine-3',5'-dibenzoate (1201895-94-4) → Deoxydifluorouridine (114248-23-6)

Guidance literature:

With ammonia; In methanol; at 23 ℃; for 23h;

DOI:10.1055/s-1992-26167

upstream raw materials:

2’-deoxy-2’,2’-difluoro-cytidine

2'-deoxy-2',2'-difluorouridine-3',5'-dibenzoate

gemcitabine hydrochloride

(2R,3R,5R)-5-(4-benzamido-2-oxopyrimidin-1(2H)-yl)-2-((benzoyloxy)methyl)-4,4-difluorotetrahydrofuran-3-yl benzoate

Downstream raw materials:

C₃₁H₃₁F₂N₃O₅

((2R,3R,5R)-3-(benzoyloxy)-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-4,4-difluorotetrahydrofuran-2-yl)methyl benzoate

Refernces

• 1、 Zheng, Zihua,Groaz, Elisabetta,Snoeck, Robert,De Jonghe, Steven,Herdewijn, Piet,Andrei, Graciela. "Influence of 4′-Substitution on the Activity of Gemcitabine and Its ProTide against VZV and SARS-CoV-2". . p. 88 - 92. Retrieved 2020/12/21.
• 2、 Wang, Guangyi,Deval, Jerome,Hong, Jin,Dyatkina, Natalia,Prhavc, Marija,Taylor, Joshua,Fung, Amy,Jin, Zhinan,Stevens, Sarah K.,Serebryany, Vladimir,Liu, Jyanwei,Zhang, Qingling,Tam, Yuen,Chanda, Sushmita M.,Smith, David B.,Symons, Julian A.,Blatt, Lawrence M.,Beigelman, Leo. "Discovery of 4′-chloromethyl-2′-deoxy-3′,5′-di- O -isobutyryl-2′-fluorocytidine (ALS-8176), A first-in-class RSV polymerase inhibitor for treatment of human respiratory syncytial virus infection". . p. 1862 - 1878. Retrieved 2015/04/22.