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-isopropylideneuridine 5'-(bis(p-nitrophenyl)phosphate)

1-(5-O-Acetyl-2,3-O-isopropylidene-β-D-ribofuranosyl)uracil

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

5'-Uridylic Acid

Refernces

Uridine 5'-diphosphate glucose analogues. Inhibitors of protein glycosylation that show antiviral activity

10.1021/jm00379a010

The research aimed to synthesize and evaluate a series of uridine 5’-diphosphate glucose analogues as inhibitors of protein glycosylation, with the goal of demonstrating their antiviral activity. The study focused on the synthesis of these analogues by reacting various protected glucose derivatives with chlorosulfonyl isocyanate and 2’,3’-O-isopropylideneuridine. The synthesized compounds were then tested for their ability to inhibit protein glycosylation in herpes simplex virus type 1 (HSV-1) infected cells and for their antiviral effects. The results showed that certain analogues, particularly compound 13, effectively inhibited protein glycosylation and exhibited significant antiviral activity against HSV-1, suggesting their potential as therapeutic agents. The study concluded that the presence of specific protecting groups on the glucose moiety influenced the antiviral efficacy, highlighting the importance of structural features in the design of effective glycosylation inhibitors.