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Basic Information
CAS No.: 161599-46-8
Name: 2',3'-Di-O-acetyl-5'-deoxy-5-fuluro-D-cytidine
Article Data: 22
Molecular Structure:
Molecular Structure of 161599-46-8 (2',3'-Di-O-acetyl-5'-deoxy-5-fuluro-D-cytidine)
Formula: C13H16FN3O6
Molecular Weight: 329.285
Synonyms: 5'-Deoxy-2',3'-di-O-acetyl-5-fluorocytidine;
EINECS: 605-260-4
Density: 1.57 g/cm3
Melting Point: 196-198?C
Boiling Point: 427.4 °C at 760 mmHg
Flash Point: 212.3 °C
Appearance: WHITE
Safety: 24/25
PSA: 122.74000
LogP: 0.32650
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1,2,3-tri-O-acetyl-5-deoxy-β-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
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%
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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

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1,2,3-tri-O-acetyl-5-deoxy-β-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
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
Raw Materials
41108-04-7
880633-97-6
27821-07-4
37076-71-4
2022-85-7
66335-38-4
108-24-7
Downstream Products
162204-20-8
124012-42-6
66335-38-4
154361-50-9
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Chemistry

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