2',3'-Isopropylideneuridine

Base Information

• Chemical Name: 2',3'-Isopropylideneuridine
• CAS No.: 362-43-6
• Molecular Formula: C12H16N2O6
• Molecular Weight: 284.269
• Hs Code.: 29339900
• European Community (EC) Number: 206-647-7
• Nikkaji Number: J34.472I
• ChEMBL ID: CHEMBL1867890
• Mol file: 362-43-6.mol

Synonyms:2',3'-O-isopropylidene uridine;2',3'-O-isopropylideneuridine;2,3-IPU

Chemical Property of 2',3'-Isopropylideneuridine

Chemical Property:

• Melting Point: 163-166 °C
• Refractive Index: 1.5460 (estimate)
• Boiling Point: 426.76°C (rough estimate)
• PKA: 9.25±0.10(Predicted)
• PSA: 102.78000
• Density: 1.376 /cm³
• LogP: -1.05360
• Storage Temp.: -20°C
• Solubility.: Chloroform (Slightly, Heated), DMSO (Slightly), Methanol (Slightly)
• XLogP3: -1.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 2
• Exact Mass: 284.10083623
• Heavy Atom Count: 20
• Complexity: 477

Purity/Quality:

98% ^*data from raw suppliers

2'',3''-O-Isopropylideneuridine ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(OC2C(OC(C2O1)N3C=CC(=O)NC3=O)CO)C
• Isomeric SMILES: CC1(O[C@@H]2[C@H](O[C@H]([C@@H]2O1)N3C=CC(=O)NC3=O)CO)C
• Description: 2',3'-Isopropylideneuridine has been shown to inhibit binding of pestivirus inhibitors by monoclonal antibodies. 2',3'-Isopropylideneuridine was also found to inhibit the replication of human immunodeficiency virus (HIV) in tissue culture by binding to the viral RNA polymerase and inhibiting its activity, preventing viral replication.
• Uses: 2′,3′-O-Isopropylideneuridine is used in the chemical synthesis of N-benzoylated uridine derivatives and N3-substituted 2′,3′-O-isopropylideneuridines with central nervous system (CNS) depressant activity. 2',3'-O-Isopropylideneuridine can be used as a useful precursor for the preparation of nucleic acids.

Technology Process of 2',3'-Isopropylideneuridine

There total 46 articles about 2',3'-Isopropylideneuridine 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%

2,2-dimethoxy-propane (77-76-9) + uridine (58-96-8) → 2',3'-O-isopropylideneuridine (362-43-6)

Guidance literature:

With toluene-4-sulfonic acid; In acetone; for 1h; Reflux;

DOI:10.1039/b926894d

Reference yield: 100.0%

acetone (67-64-1) + uridine (58-96-8) → 2',3'-O-isopropylideneuridine (362-43-6)

Guidance literature:

With sulfuric acid; at 20 ℃; for 1h;

DOI:10.1021/jm060827p

Reference yield: 99.0%

3-((benzyloxy)methyl)-1-((3aR,4R,6R,6aR)-6-(hydroxymethyl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)pyrimidine-2,4(1H,3H)-dione (191479-26-2) → 2',3'-O-isopropylideneuridine (362-43-6)

Guidance literature:

With formic acid; palladium on activated charcoal; hydrogen; In water; isopropyl alcohol; for 6h; under 760.051 Torr;

DOI:10.1016/j.tetlet.2012.05.035

upstream raw materials:

acetone

uridine

5-methoxy-N-acetyl-tryptamine

2',3'-O-isopropylidene-5-bromouridine

Downstream raw materials:

2',3'-O-isopropylidene-O²,5'-cyclouridine

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

N³-benzyl-2',3'-O-isopropylideneuridine

O^2',O^3'-isopropylidene-[5']uridylic acid diphenyl ester

Refernces

• 1、 Cornia, Mara,Menozzi, Monica,Ragg, Enzio,Mazzini, Stefania,Scarafoni, Alessio,Zanardi, Franca,Casiraghi, Giovanni. "Synthesis and utility of novel C-meso-glycosylated metalloporphyrins". . p. 3977 - 3983. Retrieved 2000.
• 2、 Ryan, Philip,Shi, Yun,von Itzstein, Mark,Rudrawar, Santosh. "Novel bisubstrate uridine-peptide analogues bearing a pyrophosphate bioisostere as inhibitors of human O-GlcNAc transferase". . . Retrieved 2021.
• 3、 Mincher, David J.,Shaw, Gordon. "A Simple Conversion of 5-Cyanouridine into Uridine". . p. 1488 - 1489. Retrieved 1986.
• 4、 Van Ostrand, Robert,Jacobsen, Casey,Delahunty, Alicia,Stringer, Carley,Noorbehesht, Ryan,Ahmed, Haidi,Awad, Ahmed M.. "Synthesis and antibacterial activity of 5′-tetrachlorophthalimido and 5′-azido 5′-deoxyribonucleosides". . p. 181 - 197. Retrieved 2017.
• 5、 Seebald, Leah,Madec, Ama?l G. E.,Imperiali, Barbara. "Deploying Fluorescent Nucleoside Analogues for High-Throughput Inhibitor Screening". . p. 108 - 112. Retrieved 2020.
• 6、 Srivastava,Rousseau. "-". . p. 455. Retrieved 1973.
• 7、 Walvoort, Marthe T. C.,Lukose, Vinita,Imperiali, Barbara. "A Modular Approach to Phosphoglycosyltransferase Inhibitors Inspired by Nucleoside Antibiotics". . p. 3856 - 3864. Retrieved 2016.
• 8、 Sontakke, Vyankat A.,L?nnberg, Harri,Ora, Mikko. "4-(Acetylthio)-2,2-dimethyl-3-oxobutyl and 4-(tert-Butyldisulfanyl)-2,2-dimethyl-3-oxobutyl as Protecting Groups for Nucleoside 5′-Phosphoramidates Derived from L -Alanine Methyl Ester". . p. 5004 - 5012. Retrieved 2015.
• 9、 Kogami, Masakazu,Koketsu, Mamoru. "An efficient method for the synthesis of selenium modified nucleosides: its application in the synthesis of Se-adenosyl-l-selenomethionine (SeAM)". . p. 9405 - 9417. Retrieved 2015.
• 10、 Jord?o, Carina I.C.,Farinha, Andreia S.F.,Enes, Roger F.,Tomé, Augusto C.,Silva, Artur M.S.,Cavaleiro, José A.S.,Ramos, Catarina I.V.,Santana-Marques,Almeida Paz, Filipe A.,de la Torre Ramirez, José M.,de la Torre, Maria D.L.,Nogueras, Manuel. "Synthesis of [60]fullerene-glycopyranosylaminopyrimidin-4-one conjugates". . p. 4427 - 4437. Retrieved 2008.