| Identification | More | [Name]
2',3'-Di-O-acetyl-5'-deoxy-5-fuluro-D-cytidine | [CAS]
161599-46-8 | [Synonyms]
2',3'-Di-O-acetyl-5'-deoxy-5-fluoro-D-cytidine
2,3-DI-O-ACETYL-5-DEOXY-5-FULURO-D-CYTIDINE
2',3'-Di-O-acetyl-5'-deoxy-5-fluoro-D-cytidine | [EINECS(EC#)]
2017-001-1 | [Molecular Formula]
C13H18FN3O6 | [MDL Number]
MFCD07369302 | [MOL File]
161599-46-8.mol | [Molecular Weight]
329.28 |
| Chemical Properties | Back Directory | [Melting point ]
196-198?C | [Boiling point ]
427.4±55.0 °C(Predicted) | [density ]
1.57±0.1 g/cm3(Predicted) | [storage temp. ]
-20°C Freezer | [solubility ]
soluble in Methanol | [form ]
powder to crystal | [pka]
2.49±0.10(Predicted) | [color ]
White to Almost white | [InChI]
InChI=1S/C13H16FN3O6/c1-5-9(22-6(2)18)10(23-7(3)19)12(21-5)17-4-8(14)11(15)16-13(17)20/h4-5,9-10,12H,1-3H3,(H2,15,16,20)/t5-,9-,10-,12-/m1/s1 | [InChIKey]
NWJBWNIUGNXJGO-YHHSPFQVSA-N | [SMILES]
C[C@H]1O[C@@H](N2C=C(F)C(N)=NC2=O)[C@H](OC(=O)C)[C@@H]1OC(=O)C | [CAS DataBase Reference]
161599-46-8(CAS DataBase Reference) |
| Hazard Information | Back Directory | [Chemical Properties]
White to Off-White Solid | [Uses]
A metabolite of Capecitabine. | [Uses]
Capecitabine intermediate | [Definition]
ChEBI: A member of the class of cytidines that is a metabolite of the drug capecitabine. | [Synthesis]
The synthesis of 2',3'-Di-O-acetyl-5'-deoxy-5-fluoro-D-cytidine requires two steps, as follows:
(1) Synthesis of 2',3'-Di-O-acetyl-5-fluorocytidine
Under nitrogen atmosphere, add 38.7 g of 2',3',5'-tri-O-acetyl-5-fluorocytidine to 200 mL of 2-methyl-2-oxobutanone. When the temperature is lowered to -5 to 0°C, add 29.5 g of (t-Bu)₂Sn(OH)Cl. Maintained at this temperature for 2 hours, then the solvent was removed under reduced pressure. The residue was filtered through silica gel (50 g, 300–400 mesh), eluted with chloroform, and the eluate concentrated to dryness under reduced pressure. A white solid (32.2 g) was obtained, yielding 93.3% with a purity of 98.6%.
(2) Synthesis of 2',3'-Di-O-acetyl-5'-deoxy-5-fluoro-D-cytidine
Under nitrogen atmosphere, add 32.2 g 2',3'-di-O-acetyl-5-fluorocytidine and 31.7 g trifluoroacetic acid to 200 mL chloroform. Maintain temperature at -10 to -5°C and add 14.1 g triethylsilane dropwise. After completion of addition, react at this temperature for 3 h. Upon completion of the reaction as indicated by TLC, the residue was washed twice with 300 ml purified water and once with 200 ml saturated sodium bicarbonate solution. After drying and evaporating to dryness, 80 g ethanol was added for recrystallisation. The mixture was cooled to 0–5°C, filtered under vacuum, and dried to yield 29.5 g of product. The yield was 96.1% with a purity of 99.7%.
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