1-[(2S,4R,5S)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]-5-iodo-pyrimidine-2,4-dione

Base Information

• Chemical Name: 1-[(2S,4R,5S)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]-5-iodo-pyrimidine-2,4-dione
• CAS No.: 162239-35-2
• Molecular Formula: C₉H₁₁IN₂O₅
• Molecular Weight: 354.101
• DSSTox Substance ID: DTXSID90858991
• Nikkaji Number: J670.135C
• Mol file: 162239-35-2.mol

Synonyms:L-IdU;SCHEMBL5983277;DTXSID90858991;1-(2-Deoxy-beta-L-erythro-pentofuranosyl)-5-iodo-2,4(1H,3H)-pyrimidinedione;1-[(2S,4R,5S)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]-5-iodo-pyrimidine-2,4-dione

Chemical Property of 1-[(2S,4R,5S)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]-5-iodo-pyrimidine-2,4-dione

Chemical Property:

• PSA: 104.81000
• LogP: -0.80580
• XLogP3: -1
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 353.97127
• Heavy Atom Count: 17
• Complexity: 386

Purity/Quality:

97% ^*data from raw suppliers

ent-Idoxuridine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1C(C(OC1N2C=C(C(=O)NC2=O)I)CO)O
• Isomeric SMILES: C1[C@H]([C@@H](O[C@@H]1N2C=C(C(=O)NC2=O)I)CO)O
• Uses: The enantiomer of Idoxuridine (I205750). Antitumor nucleoside enantiomer thymidine kinase used as potential antiviral agents.

Technology Process of 1-[(2S,4R,5S)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]-5-iodo-pyrimidine-2,4-dione

There total 29 articles about 1-[(2S,4R,5S)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]-5-iodo-pyrimidine-2,4-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%

2'-deoxyuridine (951-78-0,63844-76-8) → 5-Iodo-2'-deoxyuridine (54-42-2,162239-35-2)

Guidance literature:

With iodine; silver nitrate; In methanol; at 40 ℃; for 3h;

DOI:10.1016/j.bmc.2017.03.045 DOI:10.1016/j.bmcl.2018.04.058

Reference yield: 92.0%

3',5'-di-O-(p-toluoyl)-5-iodo-α-2'-desoxyuridine (104267-95-0) → 5-iodo-α-2'-desoxyuridine (60110-67-0,162239-35-2)

Guidance literature:

With methanol; sodium methylate; at 20 ℃; for 1h;

DOI:10.1016/j.bmcl.2006.11.052

Reference yield: 90.0%

3',5'-O-diacetyl-5-iodo-2'-deoxyuridine (1956-30-5) → 5-Iodo-2'-deoxyuridine (54-42-2,162239-35-2)

Guidance literature:

With sodium methylate; In methanol; for 1h; Ambient temperature;

DOI:10.1021/jo00303a033

upstream raw materials:

2'-deoxyuridine

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

5-trimethylstannyl-2'-deoxyuridine

5-iodouracil

Downstream raw materials:

(E)-3-(1-((2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)acrylic acid

5-iodo-α-2'-desoxyuridine

(E)-2-((bis(4-methoxyphenyl)(phenyl)methoxy)methyl)-5-(5-(4-methoxystyryl) 2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-tetrahydrofuran-3-yl cyanomethyldiisopropylphosphoramidite

(E)-1-(5-((bis(4-methoxyphenyl)(phenyl)methoxy)methyl)-4-hydroxytetrahydrofuran-2-yl)-5-(4-methoxystyryl)pyrimidine-2,4-(1H,3H)-dione

Refernces

• 1、 Hofs??, Robert,Ensslen, Philipp,Wagenknecht, Hans-Achim. "Control of helical chirality in supramolecular chromophore-DNA architectures". . p. 1330 - 1333. Retrieved 2019.
• 2、 Le, Binh Huy,Seo, Young Jun. "Direct incorporation and extension of a fluorescent nucleotide through rolling circle DNA amplification for the detection of microRNA 24-3P". . p. 2035 - 2038. Retrieved 2018.
• 3、 Romero-Pérez, Sonia,López-Martín, Isabel,Martos-Maldonado, Manuel C.,Somoza, álvaro,González-Rodríguez, David. "Synthesis of Phosphoramidite Monomers Equipped with Complementary Bases for Solid-Phase DNA Oligomerization". supporting information. p. 41 - 45. Retrieved 2020/01/03.
• 4、 Makurat, Samanta,Spisz, Paulina,Kozak, Witold,Rak, Janusz,Zdrowowicz, Magdalena. "5-iodo-4-thio-2′-deoxyuridine as a sensitizer of X-ray induced cancer cell killing". . . Retrieved 2019/05/10.