1-(3,5-Di-O-acetyl-2-deoxy-5-C-iodopentofuranosyl)-4-hydroxypyrimidin-2(1H)-one

Base Information

• Chemical Name: 1-(3,5-Di-O-acetyl-2-deoxy-5-C-iodopentofuranosyl)-4-hydroxypyrimidin-2(1H)-one
• CAS No.: 1956-30-5
• Molecular Formula: C13H15 I N2 O7
• Molecular Weight: 438.176
• Hs Code.: 29389090
• DSSTox Substance ID: DTXSID10941339
• Mol file: 1956-30-5.mol

Synonyms:DTXSID10941339;1-(3,5-Di-O-acetyl-2-deoxy-5-C-iodopentofuranosyl)-4-hydroxypyrimidin-2(1H)-one

Chemical Property of 1-(3,5-Di-O-acetyl-2-deoxy-5-C-iodopentofuranosyl)-4-hydroxypyrimidin-2(1H)-one

Chemical Property:

• Melting Point: 161-163 °C
• Boiling Point: °Cat760mmHg
• Flash Point: °C
• PSA: 116.69000
• Density: 1.81g/cm³
• LogP: -0.07650
• Storage Temp.: -20°C
• XLogP3: 0.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 6
• Exact Mass: 437.99240
• Heavy Atom Count: 23
• Complexity: 565

Purity/Quality:

99% ^*data from raw suppliers

3'',5''-Di-O-acetyl-2''-deoxy-5-iodouridine ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)OC1CC(OC1C(OC(=O)C)I)N2C=CC(=O)NC2=O

Technology Process of 1-(3,5-Di-O-acetyl-2-deoxy-5-C-iodopentofuranosyl)-4-hydroxypyrimidin-2(1H)-one

There total 7 articles about 1-(3,5-Di-O-acetyl-2-deoxy-5-C-iodopentofuranosyl)-4-hydroxypyrimidin-2(1H)-one 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: 99.0%

5-Iodo-2'-deoxyuridine (54-42-2,162239-35-2) + acetic anhydride (108-24-7) → 3',5'-O-diacetyl-5-iodo-2'-deoxyuridine (1956-30-5)

Guidance literature:

With pyridine; at 20 ℃; for 16.5h;

DOI:10.1080/15257770701501534

Reference yield: 96.0%

3',5'-di-O-acetyl-2'-deoxyuridine (13030-62-1) → 3',5'-O-diacetyl-5-iodo-2'-deoxyuridine (1956-30-5)

Guidance literature:

With ammonium cerium (IV) nitrate; 1-ethylene glycol monomethyl ether-3-methylimidazolium methanesulfonate; lithium iodide; at 80 ℃; for 0.333333h;

DOI:10.1080/15257770903170252

Reference yield: 95.0%

5-Iodo-2'-deoxyuridine (54-42-2,162239-35-2) + acetyl chloride (75-36-5) → 3',5'-O-diacetyl-5-iodo-2'-deoxyuridine (1956-30-5)

Guidance literature:

With acetic anhydride; acetic acid; 1.) 0 deg C, 1 h, 2.) RT, 24 h;

DOI:10.1021/jm00358a028

upstream raw materials:

5-Iodo-2'-deoxyuridine

acetic anhydride

acetyl chloride

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

Downstream raw materials:

5-Iodo-2'-deoxyuridine

2'-deoxy-4-thiouridine

5-trifluoromethyl-2′-deoxyuridine-3′,5′-diacetate

2'-deoxy-5-trifluoromethyluridine

Refernces

• 1、 Esho, Noor,Desaulniers, Jean-Paul,Davies, Brian,Chui, Helen M.-P.,Rao, Meneni Srinivasa,Chow, Christine S.,Szafert, Slawomir,Dembinski, Roman. "NMR conformational analysis of p-tolyl furanopyrimidine 2′-deoxyribonucleoside and crystal structure of its 3′,5′-di- O-acetyl derivative". . p. 1231 - 1238. Retrieved 2005.
• 2、 Zhang, Xiao-Hui,Yin, Hong-Yan,Trigiante, Giuseppe,Brem, Reto,Karran, Peter,Pitak, Mateusz B.,Coles, Simon J.,Xu, Yao-Zhong. "5-Iodo-4-thio-2′-deoxyuridine: Synthesis, structure, and cytotoxic activity". . p. 147 - 149. Retrieved 2015.
• 3、 Park, Sun Min,Yang, Heeju,Park, Song-Kyu,Kim, Hwan Mook,Kim, Byeang Hyean. "Design, synthesis, and anticancer activities of novel perfluoroalkyltriazole-appended 2′-deoxyuridines". . p. 5831 - 5834. Retrieved 2010.
• 4、 Durand, Adeline,Brown, Tom. "Synthesis and properties of oligonucleotides containing a cholesterol thymidine monomer". . p. 785 - 794. Retrieved 2007.
• 5、 Chen, Zhixing,Paley, Daniel W.,Wei, Lu,Weisman, Andrew L.,Friesner, Richard A.,Nuckolls, Colin,Min, Wei. "Multicolor live-cell chemical imaging by isotopically edited alkyne vibrational palette". . p. 8027 - 8033. Retrieved 2014.
• 6、 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.