| Identification | More | [Name]
5-Iodo-2'-deoxycytidine | [CAS]
611-53-0 | [Synonyms]
2'-DEOXY-5-IODOCYTIDINE
5-IDC
5-IODO-2'-DEOXYCYTIDINE
IBACITABINE
IDC
2'-Deoxy-5-iodo-D-cytidine
5-IODO-2''-DEOXYCYTIDINE(5-IDC)
5-IODO-2''-DEOXYCYTIDINE HPLC 99%
4-Amino-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-iodopyrimidin-2-one
2''-DEOXY-5-IODOCYTIDINE (5-IODO-2''-DEOXYCYTIDINE: 5-IDC)
Idoxcitidin
NSC-527083 | [EINECS(EC#)]
210-269-8 | [Molecular Formula]
C9H12IN3O4 | [MDL Number]
MFCD00038063 | [Molecular Weight]
353.11 | [MOL File]
611-53-0.mol |
| Chemical Properties | Back Directory | [Melting point ]
180-183℃ | [Boiling point ]
522.1±60.0 °C(Predicted) | [density ]
2.37±0.1 g/cm3(Predicted) | [storage temp. ]
Store at 0°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 Data | Back Directory | [Hazard Codes ]
Xn,T | [Risk Statements ]
R22:Harmful if swallowed.
R63:Possible risk of harm to the unborn child.
R42/43:May cause sensitization by inhalation and skin contact .
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S23:Do not breathe gas/fumes/vapor/spray (appropriate wording to be specified by the manufacturer) .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection . | [WGK Germany ]
3 | [HS Code ]
29071212 |
| Hazard Information | Back Directory | [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 |
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