5-Fluoro-1-((3aR,4R,6R,6aR)-6-(hydroxymethyl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)pyrimidine-2,4(1H,3H)-dione

Base Information

• Chemical Name: 5-Fluoro-1-((3aR,4R,6R,6aR)-6-(hydroxymethyl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)pyrimidine-2,4(1H,3H)-dione
• CAS No.: 2797-17-3
• Molecular Formula: C12H15 F N2 O6
• Molecular Weight: 302.259
• Nikkaji Number: J403.919J
• Mol file: 2797-17-3.mol

Synonyms:2797-17-3;5-Fluoro-1-((3aR,4R,6R,6aR)-6-(hydroxymethyl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)pyrimidine-2,4(1H,3H)-dione;C12H15FN2O6;C12-H15-F-N2-O6;SCHEMBL6512158;LHTMLCXJMYPWGR-FDDDBJFASA-N;5-Fluoro-2'-O,3'-O-(propane-2,2-diyl)uridine

Chemical Property of 5-Fluoro-1-((3aR,4R,6R,6aR)-6-(hydroxymethyl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)pyrimidine-2,4(1H,3H)-dione

Chemical Property:

• Melting Point: 196-198°C
• Boiling Point: °Cat760mmHg
• PKA: 7.48±0.10(Predicted)
• Flash Point: °C
• PSA: 102.78000
• Density: 1.54g/cm³
• LogP: -0.91450
• Storage Temp.: Refrigerator
• XLogP3: -1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 2
• Exact Mass: 302.09141436
• Heavy Atom Count: 21
• Complexity: 522

Purity/Quality:

97% ^*data from raw suppliers

2'',3''-O-Isopropylidene-5-fluorouridine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(OC2C(OC(C2O1)N3C=C(C(=O)NC3=O)F)CO)C
• Isomeric SMILES: CC1(O[C@@H]2[C@H](O[C@H]([C@@H]2O1)N3C=C(C(=O)NC3=O)F)CO)C
• Uses: Suppressed in vitro primary antibody response toward sheep red blood cells (SRBC).

Technology Process of 5-Fluoro-1-((3aR,4R,6R,6aR)-6-(hydroxymethyl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)pyrimidine-2,4(1H,3H)-dione

There total 10 articles about 5-Fluoro-1-((3aR,4R,6R,6aR)-6-(hydroxymethyl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)pyrimidine-2,4(1H,3H)-dione 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%

5-fluorouridine (316-46-1) + acetone (67-64-1) → 2',3'-O-isopropylidene-5-fluorouridine (2797-17-3)

Guidance literature:

With sulfuric acid; at 0 - 20 ℃; Inert atmosphere;

DOI:10.1021/jm801224t

Reference yield: 91.0%

dimethoxypropane (4744-10-9) + 5-fluorouridine (316-46-1) → 2',3'-O-isopropylidene-5-fluorouridine (2797-17-3)

Guidance literature:

With p-toluenesulfonic acid monohydrate; In acetone; for 1.66667h; Heating / reflux;

Reference yield: 90.0%

5-fluorouridine (316-46-1) + 2,2-dimethoxy-propane (77-76-9) → 2',3'-O-isopropylidene-5-fluorouridine (2797-17-3)

Guidance literature:

With toluene-4-sulfonic acid; In acetone; Ambient temperature;

DOI:10.1021/jm00139a026

upstream raw materials:

2',3'-O-isopropylideneuridine

5-fluorouridine

2,2-dimethoxy-propane

2',3'-O-Isopropylidene-3-(4-methoxybenzyl)-5-fluorouridine

Downstream raw materials:

(5-fluorouridine)-5'-phosphoric acid (3-dodecylthio-2-decyloxy)propyl ester

5-fluoro-6-iodouridine

1-((2R,3R,4S,5R)-3,4-Dihydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-5-fluoro-6-phenylsulfanyl-1H-pyrimidine-2,4-dione

5-Fluoro-1-((3aR,4R,6R,6aR)-6-methoxymethoxymethyl-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-6-phenylsulfanyl-1H-pyrimidine-2,4-dione

Refernces

• 1、 Slusarczyk, Magdalena,Ferla, Salvatore,Brancale, Andrea,McGuigan, Christopher. "Synthesis and biological evaluation of 6-substituted-5-fluorouridine ProTides". . p. 551 - 565. Retrieved 2018.
• 2、 -. "CANCER THERAPY WITH MICROBUBBLES.". Page/Page column 24. . Retrieved 2021/10/11.
• 3、 Meltzer, Diana,Ethan, Ophir,Arguin, Guillaume,Nadel, Yael,Danino, Ortal,Lecka, Joanna,Sévigny, Jean,Gendron, Fernand-Pierre,Fischer, Bilha. "Synthesis and structure-activity relationship of uracil nucleotide derivatives towards the identification of human P2Y6 receptor antagonists". . p. 5764 - 5773. Retrieved 2015/11/11.