Uridine, 2'-deoxy-4-thio-

Base Information

• Chemical Name: Uridine, 2'-deoxy-4-thio-
• CAS No.: 5580-20-1
• Molecular Formula: C9H12N2O4S
• Molecular Weight: 244.271
• NSC Number: 517771
• DSSTox Substance ID: DTXSID90971199
• Mol file: 5580-20-1.mol

Synonyms:4-thio-2'-deoxyuridine;4-thiodeoxyuridine

Chemical Property of Uridine, 2'-deoxy-4-thio-

Chemical Property:

• Boiling Point: 473°Cat760mmHg
• Flash Point: 239.9°C
• PSA: 119.57000
• Density: 1.54g/cm³
• LogP: -0.45340
• Storage Temp.: ?20°C
• XLogP3: -1
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 244.05177804
• Heavy Atom Count: 16
• Complexity: 346

Purity/Quality:

97% ^*data from raw suppliers

2'-Deoxy-4-thiouridine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(C(OC1N2C=CC(=S)NC2=O)CO)O

Technology Process of Uridine, 2'-deoxy-4-thio-

There total 4 articles about Uridine, 2'-deoxy-4-thio- 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:

3',5'-di-O-acetyl-2'-deoxyuridine (13030-62-1) → 5-Iodo-2'-deoxyuridine (54-42-2,162239-35-2) + C9H11IN2O5S + C18H20I2N4O8S2 + C18H21IN4O8S2 + 2'-deoxy-4-thiouridine (5580-20-1)

Guidance literature:

Multi-step reaction with 4 steps

1: ammonium cerium (IV) nitrate; iodine / acetonitrile / 1 h / 80 °C

2: tetraphosphorus decasulfide / 1,4-dioxane / Reflux

3: sodium hydride / methanol / 0.17 h / 0 - 20 °C

4: aq. phosphate buffer; tert-butyl alcohol / Radiolysis

With ammonium cerium (IV) nitrate; tetraphosphorus decasulfide; iodine; sodium hydride; In 1,4-dioxane; methanol; aq. phosphate buffer; acetonitrile; tert-butyl alcohol;

DOI:10.3390/ijms20061308

Reference yield:

3',5'-O-diacetyl-5-iodo-2'-deoxyuridine (1956-30-5) → 5-Iodo-2'-deoxyuridine (54-42-2,162239-35-2) + C9H11IN2O5S + C18H20I2N4O8S2 + C18H21IN4O8S2 + 2'-deoxy-4-thiouridine (5580-20-1)

Guidance literature:

Multi-step reaction with 3 steps

1: tetraphosphorus decasulfide / 1,4-dioxane / Reflux

2: sodium hydride / methanol / 0.17 h / 0 - 20 °C

3: aq. phosphate buffer; tert-butyl alcohol / Radiolysis

With tetraphosphorus decasulfide; sodium hydride; In 1,4-dioxane; methanol; aq. phosphate buffer; tert-butyl alcohol;

DOI:10.3390/ijms20061308

Reference yield:

2'-deoxyuridine (951-78-0,63844-76-8) → 5-Iodo-2'-deoxyuridine (54-42-2,162239-35-2) + C9H11IN2O5S + C18H20I2N4O8S2 + C18H21IN4O8S2 + 2'-deoxy-4-thiouridine (5580-20-1)

Guidance literature:

Multi-step reaction with 5 steps

1: pyridine / 24 h / 20 °C

2: ammonium cerium (IV) nitrate; iodine / acetonitrile / 1 h / 80 °C

3: tetraphosphorus decasulfide / 1,4-dioxane / Reflux

4: sodium hydride / methanol / 0.17 h / 0 - 20 °C

5: aq. phosphate buffer; tert-butyl alcohol / Radiolysis

With pyridine; ammonium cerium (IV) nitrate; tetraphosphorus decasulfide; iodine; sodium hydride; In 1,4-dioxane; methanol; aq. phosphate buffer; acetonitrile; tert-butyl alcohol;

DOI:10.3390/ijms20061308

upstream raw materials:

3',5'-di-O-acetyl-2'-deoxyuridine

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

5-iodo-4-thio-2'-deoxyuridine

2'-deoxyuridine

Downstream raw materials:

5'-O-dimethoxytrityl-4-S-pivaloyloxymethyl-2'-deoxy-4-thiouridine

5'-O-dimethoxytrityl-4-(S-pivaloyloxymethyl)-2'-deoxy-4-thiouridin-3'-yl hydrogenphosphonate

C₄₈H₅₅N₄O₁₆PS

C₄₈H₅₅N₄O₁₆PS

Refernces