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2',3'-Di-O-acetyl-5'-deoxy-5-fuluro-D-cytidine

  • Name 2',3'-Di-O-acetyl-5'-deoxy-5-fuluro-D-cytidine
  • EINECS605-260-4
  • CAS No. 161599-46-8
  • Density1.57 g/cm3
  • PSA122.74000
  • LogP0.32650
  • SolubilityN/A
  • Melting Point196-198?C
  • FormulaC13H16FN3O6
  • Boiling Point427.4 °C at 760 mmHg
  • Molecular Weight329.285
  • Flash Point212.3 °C
  • Transport InformationN/A
  • AppearanceWHITE
  • Safety24/25
  • Risk CodesN/A
  • Molecular Structure
    Molecular Structure of 161599-46-8 (2',3'-Di-O-acetyl-5'-deoxy-5-fuluro-D-cytidine)
  • Hazard SymbolsN/A
  • SynonymsN/A
  • Article Data22

2',3'-Di-O-acetyl-5'-deoxy-5-fuluro-D-cytidine Synthetic route

2022-85-7

Flucytosine

161599-46-8

(2R,3R,4R,5R)-2-(4-amino-5-fluoro-2-oxopyrimidin-1(2H)-yl)-5-methyl-tetrahydrofuran-3,4-diyl diacetate

Conditions
ConditionsYield
With titanium tetrachloride In dichloromethane at 10 - 20℃; for 4h; Solvent;88.6%
Stage #1: Flucytosine With ammonium sulfate; 1,1,1,3,3,3-hexamethyl-disilazane In toluene for 3h; Reflux;
Stage #2: 1,2,3-tri-O-acetyl-5-deoxy-β-D-ribofuranose With tin(IV) chloride In dichloromethane at -5℃; Inert atmosphere; Heating;
83.6%
Stage #1: Flucytosine With trifluorormethanesulfonic acid; 1,1,1,3,3,3-hexamethyl-disilazane In acetonitrile for 2h; Reflux;
Stage #2: 1,2,3-tri-O-acetyl-5-deoxy-β-D-ribofuranose With trifluorormethanesulfonic acid at 20 - 55℃;
80%
110022-91-8

di-O-acetyl-5-deoxy-ξ-D-ribofuranosyl chloride

111878-21-8

2-trimethylsilyloxy-4-trimethylsilylamino-5-fluoropyrimidine

161599-46-8

(2R,3R,4R,5R)-2-(4-amino-5-fluoro-2-oxopyrimidin-1(2H)-yl)-5-methyl-tetrahydrofuran-3,4-diyl diacetate

Conditions
ConditionsYield
Stage #1: di-O-acetyl-5-deoxy-ξ-D-ribofuranosyl chloride; 2-trimethylsilyloxy-4-trimethylsilylamino-5-fluoropyrimidine In 1,2-dichloro-ethane for 4h; Inert atmosphere; Schlenk technique; Reflux;
Stage #2: With water Inert atmosphere; Schlenk technique;
86%
41108-04-7

5-fluoro-2-trimethylsilanyloxy-pyrimidin-4-ylamine

161599-46-8

(2R,3R,4R,5R)-2-(4-amino-5-fluoro-2-oxopyrimidin-1(2H)-yl)-5-methyl-tetrahydrofuran-3,4-diyl diacetate

Conditions
ConditionsYield
With tin(IV) chloride; sodium hydrogencarbonate In dichloromethane; water at 0 - 20℃; for 0.5h;78.4%
37076-71-4

5-deoxy-1,2,3-tri-O-acetyl-D-ribofuranose

5-fluorocytosine

161599-46-8

(2R,3R,4R,5R)-2-(4-amino-5-fluoro-2-oxopyrimidin-1(2H)-yl)-5-methyl-tetrahydrofuran-3,4-diyl diacetate

Conditions
ConditionsYield
Stage #1: 5-fluorocytosine With 1,1,1,3,3,3-hexamethyl-disilazane In toluene for 4h; Autoclave; Reflux; Industrial scale;
Stage #2: 5-deoxy-1,2,3-tri-O-acetyl-D-ribofuranose With tin(IV) chloride In dichloromethane at 2 - 20℃; for 12h; Industrial scale;
74%
66335-38-4

5'-deoxy-5-fluorocytidine

161599-46-8

(2R,3R,4R,5R)-2-(4-amino-5-fluoro-2-oxopyrimidin-1(2H)-yl)-5-methyl-tetrahydrofuran-3,4-diyl diacetate

Conditions
ConditionsYield
With acetic anhydride In pyridine; water
880633-97-6

5'-deoxy-2',3'-di-O-acetyl-5-fluoro-N4-((5-nitrothien-2-yl)methoxycarbonyl)cytidine

161599-46-8

(2R,3R,4R,5R)-2-(4-amino-5-fluoro-2-oxopyrimidin-1(2H)-yl)-5-methyl-tetrahydrofuran-3,4-diyl diacetate

Conditions
ConditionsYield
In water; isopropyl alcohol G-values; Irradiation;
108-24-7

acetic anhydride

66335-38-4

5'-deoxy-5-fluorocytidine

161599-46-8

(2R,3R,4R,5R)-2-(4-amino-5-fluoro-2-oxopyrimidin-1(2H)-yl)-5-methyl-tetrahydrofuran-3,4-diyl diacetate

Conditions
ConditionsYield
With pyridine at 0℃; for 3h;
With pyridine at 0℃; for 3h;
2022-85-7

Flucytosine

37076-71-4

5-deoxy-1,2,3-tri-O-acetyl-D-ribofuranose

161599-46-8

(2R,3R,4R,5R)-2-(4-amino-5-fluoro-2-oxopyrimidin-1(2H)-yl)-5-methyl-tetrahydrofuran-3,4-diyl diacetate

Conditions
ConditionsYield
Stage #1: Flucytosine With chloro-trimethyl-silane; 1,1,1,3,3,3-hexamethyl-disilazane In toluene at 110℃; for 0.5h;
Stage #2: 5-deoxy-1,2,3-tri-O-acetyl-D-ribofuranose With tin(IV) chloride In dichloromethane at 0 - 30℃;
Stage #3: With water; sodium hydrogencarbonate In dichloromethane for 2h;
37076-71-4

5-deoxy-1,2,3-tri-O-acetyl-D-ribofuranose

41108-04-7

5-fluoro-2-trimethylsilanyloxy-pyrimidin-4-ylamine

161599-46-8

(2R,3R,4R,5R)-2-(4-amino-5-fluoro-2-oxopyrimidin-1(2H)-yl)-5-methyl-tetrahydrofuran-3,4-diyl diacetate

Conditions
ConditionsYield
tin(IV) chloride In dichloromethane at 0℃; for 2h;
128963-10-0

2',3',5'-tri-O-acetyl-5-fluorocytidine

161599-46-8

(2R,3R,4R,5R)-2-(4-amino-5-fluoro-2-oxopyrimidin-1(2H)-yl)-5-methyl-tetrahydrofuran-3,4-diyl diacetate

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: pyridine / dichloromethane / 1.5 h / 0 °C
2: alcalase enzyme cross linked aggregate / ethanol / 100 h / 20 °C / Enzymatic reaction
3: carbon tetrabromide / dichloromethane / 3 h / 20 °C / Inert atmosphere
4: 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride / tetrahydrofuran / Reflux
View Scheme

2',3'-Di-O-acetyl-5'-deoxy-5-fuluro-D-cytidine Chemical Properties

Product Name: Cytidine,5'-deoxy-5-fluoro-, 2',3'-diacetate
Synonyms of Cytidine,5'-deoxy-5-fluoro-, 2',3'-diacetate (CAS NO.161599-46-8): 2',3'-Di-O-acetyl-5'-deoxy-5-fuluro-D-cytidine
CAS NO: 161599-46-8
Molecular Formula: C13H16FN3O6
Molecular Weight of Cytidine,5'-deoxy-5-fluoro-, 2',3'-diacetate (CAS NO.161599-46-8): 329.281
Molecular Structure:

H bond acceptors: 9
H bond donors: 2
Freely Rotating Bonds: 5
Polar Surface Area: 97.74 Å2
Index of Refraction: 1.609
Molar Refractivity: 72.32 cm3
Molar Volume: 208.7 cm3
Surface Tension: 51.7 dyne/cm
Density of Cytidine,5'-deoxy-5-fluoro-, 2',3'-diacetate (CAS NO.161599-46-8): 1.57 g/cm3
Flash Point: 212.3 °C
Enthalpy of Vaporization: 68.24 kJ/mol
Boiling Point: 427.4 °C at 760 mmHg
Vapour Pressure: 1.64E-07 mmHg at 25°C

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