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2-IODOADENOSINE

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2-IODOADENOSINE Basic information
Product Name:2-IODOADENOSINE
Synonyms:2-Iodo-D-adenosine;(2R,3R,4R,5R)-2-(6-AMINO-2-IODO-PURIN-9-YL)-5-(HYDROXYMETHYL)OXOLANE-3,4-DIOL(2-IODOADENOSINE);2-IODOADENOSINE;6-Amino-2-iodo-9-(beta-D-ribofuranosyl)purine;(2R,3R,4S,5R)-2-(6-aMino-2-iodo-9H-purin-9-yl)-5-(hydroxyMethyl)tetrahydrofuran-3,4-diol;(4S,2R,3R,5R)-2-(6-amino-2-iodopurin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol;2-Iodoadenosine>;Adenosine, 2-iodo-
CAS:35109-88-7
MF:C10H12IN5O4
MW:393.14
EINECS:623-798-8
Product Categories:Carbohydrates & Derivatives;Intermediates & Fine Chemicals;Pharmaceuticals;Nucleotides and Nucleosides;Bases & Related Reagents;Nucleotides;Nucleosides;Oligonucleotide Synthesis;Specialty Synthesis
Mol File:35109-88-7.mol
2-IODOADENOSINE Structure
2-IODOADENOSINE Chemical Properties
Melting point 200 °C (dec.)
Boiling point 776.3±70.0 °C(Predicted)
density 2.69±0.1 g/cm3(Predicted)
storage temp. Keep in dark place,Inert atmosphere,Room temperature
solubility DMSO, Methanol, Water
form Solid
pka13.05±0.70(Predicted)
color Off-White to Pale Yellow
λmax265nm(H2O)(lit.)
InChIKeyMGEBVSZZNFOIRB-UUOKFMHZSA-N
CAS DataBase Reference35109-88-7(CAS DataBase Reference)
Safety Information
Hazard Codes Xi
Risk Statements 36/37/38
Safety Statements 26
WGK Germany 3
HS Code 29349990
MSDS Information
2-IODOADENOSINE Usage And Synthesis
Description2-Iodoadenosine is a chemical compound that is produced from the oxidation of uridine. It is used in the synthesis of peptides, which are important for biological processes like signal transduction and cell growth.
Chemical PropertiesOff-White Crystalline Solid
Synthesis
ACETIC ACID (2R,3R,4R,5R)-3,4-DIACETOXY-5-(6-CHLORO-2-IODO-PURIN-9-YL)-TETRAHYDRO-FURAN-2-YLMETHYL ESTER

5987-76-8

2-IODOADENOSINE

35109-88-7

GENERAL STEPS: To a flask containing 6.0 g (11.1 mmol) of (2R,3R,4R,5R)-2-(acetyloxymethyl)-5-(6-chloro-2-iodo-9H-purin-9-yl)tetrahydrofuran-3,4-diyldiacetate was added 100 mL of liquid NH3 at -78 °C with continuous stirring for 6 hours. Subsequently, the reaction mixture was slowly warmed to room temperature and the NH3 was evaporated overnight to give a brown oil. The product was purified by hot isopropanol crystallization to give 2-iodoadenosine (80% yield, melting point 143-145°C). Thin layer chromatographic analysis (20% MeOH/CHCl3) showed an Rf value of 0.6. 1H NMR (300 MHz, DMSO-d6) δ 8.24 (s, 1H), 7.68 (s, 2H), 5.75 (d, J = 6.16 Hz, 1H), 5.42 (d, J = 5.40 Hz, 1H), 5.16 (d, J = 4.62 Hz , 1H), 4.99 (t, J = 5.39 Hz, 1H), 4.67 (d, J = 4.81 Hz, 1H), 4.06 (d, J = 3.37 Hz, 1H), 3.89 (m, 1H), 3.54 (m, 2H).

References[1] Journal of Organic Chemistry, 1985, vol. 50, # 3, p. 406 - 408
[2] Chemical and Pharmaceutical Bulletin, 1985, vol. 33, # 4, p. 1766 - 1769
[3] Journal of Organic Chemistry, 1988, vol. 53, # 13, p. 3051 - 3057
[4] Journal of Medicinal Chemistry, 1992, vol. 35, # 2, p. 241 - 252
[5] Patent: US4956345, 1990, A
Tag:2-IODOADENOSINE(35109-88-7) Related Product Information
Vidarabine 2-Fluoroadenosine Adenosine 5'-monophosphate PROMETHAZINE Aminophylline S-ADENOSYL-L-METHIONINE Doxofylline Adenosine Cyclic adenosine monophosphate 2-Iodopyrimidine 2-Iodoadenine 2-IODOADENOSINE 2-IODO-5'-ETHYLCARBOXAMIDOADENOSINE 2-IODOADENOSINE 2',3'-ACETONIDE 2-Azido-6-iodoadenosine 2-IODOADENOSINE 5'-CARBOXY-2',3'-ACETONIDE TFA & 2-IODOADENOSINE 2'-deoxy-2'-iodoadenosine-5'-triphosphate

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