5-Iodo-2'-deoxycytidine Chemical Properties

Melting point:

180-183℃

Boiling point:

522.1±60.0 °C(Predicted)

Density 

2.37±0.1 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Store in freezer, under -20°C

solubility 

DMSO:100.0(Max Conc. mg/mL);283.19(Max Conc. mM)

form 

Powder

pka

14.03±0.60(Predicted)

color 

White

Water Solubility 

Slightly soluble in water.

InChI

InChI=1S/C9H12IN3O4/c10-4-2-13(9(16)12-8(4)11)7-1-5(15)6(3-14)17-7/h2,5-7,14-15H,1,3H2,(H2,11,12,16)/t5-,6+,7+/m0/s1

InChIKey

WEVJJMPVVFNAHZ-UHFFFAOYSA-N

SMILES

OC[C@H]1O[C@@H](N2C=C(I)C(N)=NC2=O)C[C@@H]1O

CAS DataBase Reference

611-53-0(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn,T

Risk Statements 

22-63-42/43-36/37/38

Safety Statements 

23-26-36/37/39-24/25

WGK Germany 

3

HS Code 

29071212

5-Iodo-2'-deoxycytidine Usage And Synthesis

Description

5-Iodo-2'-deoxycytidine is an iodinated analog of deoxycytidine and acts as an anti-viral agent.

Chemical Properties

White crystals or powder

Uses

5-Iodo-2'-deoxycytidine is used in the construction of DNA oligomers to enable structural studies and photoactivated cross-linking. It is used in the synthesis of other modified nucleosides, such as 5-ethynylferrocenyl-2?-deoxycytidine used in semiconductor electrodes and 10-(2-deoxyβ-D-ribofuranosyl)pyrimido[4?,5?:4,5]pyrimido[1,6-a]indole-6,9(7H)-dione (dCPPI).

Definition

ChEBI: Ibacitabine is a pyrimidine 2'-deoxyribonucleoside.

Synthesis

General procedure for the synthesis of 4-amino-1-((2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyrimidin-2(1H)-one (dC) from 4-amino-1-((2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-5-iodopyrimidin-2(1H)-one: in a flame-dried round-bottom flask In a flame-dried round-bottom flask, 10.0 g of dC (44.0 mmol, 1.0 eq.), 7.70 g of iodine (26.4 mmol, 0.6 eq.) and 11.4 g of mCPBA (70%, 46.2 mmol, 1.05 eq.) were dissolved in 120 mL of DMF. The reaction mixture was stirred at room temperature for 2 h and subsequently evaporated to dryness (a small amount of DMF residue was acceptable in subsequent column chromatography). Purification by column chromatography (eluent ratio: DCM/MeOH/H2O/NH3 190:10:0.6:0.6 → 90:10:0.6:0.6) afforded 9.71 g (63% yield) of target compound 1 as an orange solid. The product characterization data were as follows: 1H NMR (400 MHz, CDCl3/MeOD) δ (ppm) = 8.46 (s, 1H), 6.13 (t, 3J = 6.0 Hz, 1H), 4.34 (dt, 3J = 4.7, 6.3 Hz, 1H), 3.93 (dt, 3J = 3.0, 4.3 Hz, 1H), 3.84 (dd. 3J = 3.0, 2J = 12.1 Hz, 1H), 3.72 (dd, 3J = 3.2, 2J = 12.1 Hz, 1H), 2.39 (dd, 3J = 4.8, 6.3, 2J = 13.7 Hz, 1H), 2.20-2.09 (m, 1H).13C NMR (101 MHz, MeOD) δ (ppm) = 163.9, 153.9, 150.9, 89.5, 88.3, 71.5, 62.2, 56.2, 42.5. HRMS (ESI+) Calculated C9H13IN3O4+ [M+H]+: 353.9945, Measured: 353.9944. Melting point range: 133-135°C (Decomposition). IR (ATR). 3191 (w), 1718 (m), 1642 (s), 1286 (m), 1087 (s), 957 (s), 750 (m).

References

[1] Organic Letters, 2010, vol. 12, # 24, p. 5671 - 5673
[2] Patent: WO2012/62907, 2012, A1. Location in patent: Page/Page column 13; 14
[3] Patent: US2013/237697, 2013, A1. Location in patent: Paragraph 0052-0055
[4] Synthesis, 2009, # 23, p. 3957 - 3962
[5] Patent: US2012/178919, 2012, A1. Location in patent: Page/Page column 4

5-Iodo-2'-deoxycytidine(611-53-0)Related Product Information

• Zalcitabine
• 1-beta-D-Arabinofuranosylcytosine hydrochloride
• ALTRENOGEST
• 3-Aminophenol
• 5-Azacytidine
• 6-Aminocaproic acid
• Cytidine-5'-triphosphate disodium salt dihydrate
• Cytarabine
• Glycine
• CHLOROPHOSPHONAZO III
• 2'-Deoxycytidine monohydrate
• Tris(hydroxymethyl)aminomethane
• 5-Iodocytidine
• Fiacitabine
• Cytidine
• 2'-Deoxycytidine
• 2''-DEOXY-2''-FLUORO-5-IODOCYTIDINE
• 5'-O-(DMT)-N4-(DMF)-5-IODO-2'-DEOXYCYTIDINE,5'-O-(DIMETHOXYTRITYL)-N4-DIMETHYLAMINOMETHYLIDENE-5-IODO-2'-DEOXYCYTIDINE