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162204-20-8

Basic Information
CAS No.: 162204-20-8
Name: 5`-deoxy-5-fluore-N-[(pentoyloxy)carbonyl]cytidine 2`,3`-diacetate
Article Data: 21
Molecular Structure:
Molecular Structure of 162204-20-8 (5`-deoxy-5-fluore-N-[(pentoyloxy)carbonyl]cytidine 2`,3`-diacetate)
Formula: C19H26FN3O8
Molecular Weight: 443.429
Synonyms: Carbamicacid, [1-(2,3-di-O-acetyl-5-deoxy-b-D-ribofuranosyl)-5-fluoro-1,2-dihydro-2-oxo-4-pyrimidinyl]-, pentylester;2',3'-Di-O-acetyl-5'-deoxy-5-fluoro-N4-(pentyloxycarbonyl)cytidine;
EINECS: 700-593-2
Density: 1.4 g/cm3
Melting Point: 100-102?C
Appearance: Powder
Safety: 24/25
PSA: 135.05000
LogP: 1.97480
Synthetic route
638-41-5

pentyl chloroformate

161599-46-8

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

162204-20-8

N1-(2',3'-di-O-acetyl-5'-deoxy-β-D-ribofuranosyl)-5-fluoro-N4-(pentyloxycarbonyl)cytosine

Conditions
ConditionsYield
With potassium phosphate In dichloromethane; isopropyl alcohol at 0 - 25℃; for 4h; Reagent/catalyst; Inert atmosphere;94.2%
With pyridine In dichloromethane at 0℃; for 1h;93%
With dmap; potassium carbonate In dichloromethane at 5℃; for 0.75h; Temperature; Solvent; Reagent/catalyst;90.6%
862508-03-0

(5-fluoro-2-oxo-1,2-dihydropyrimidin-4-yl)carbamic acid amyl ester

C24H24O7

162204-20-8

N1-(2',3'-di-O-acetyl-5'-deoxy-β-D-ribofuranosyl)-5-fluoro-N4-(pentyloxycarbonyl)cytosine

Conditions
ConditionsYield
Stage #1: (5-fluoro-2-oxo-1,2-dihydropyrimidin-4-yl)carbamic acid amyl ester With N,O-Bis(trimethylsilyl)trifluoroacetamide In acetonitrile at 50℃; for 0.5h; Inert atmosphere;
Stage #2: C24H24O7 In acetonitrile at 20℃; for 0.75h; Inert atmosphere; Molecular sieve;
Stage #3: With N-iodo-succinimide; trimethylsilyl trifluoromethanesulfonate In acetonitrile at 0 - 20℃; for 2h;
93%
71-41-0

pentan-1-ol

530-62-1

1,1'-carbonyldiimidazole

161599-46-8

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

162204-20-8

N1-(2',3'-di-O-acetyl-5'-deoxy-β-D-ribofuranosyl)-5-fluoro-N4-(pentyloxycarbonyl)cytosine

Conditions
ConditionsYield
In dichloromethane at 20℃; for 4h;91.6%

5'-iodo-2',3'-di-O-acetyl-5-fluoro-N4-(pentyloxycarbonyl)cytidine

162204-20-8

N1-(2',3'-di-O-acetyl-5'-deoxy-β-D-ribofuranosyl)-5-fluoro-N4-(pentyloxycarbonyl)cytosine

Conditions
ConditionsYield
With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride In tetrahydrofuran at 20℃; for 4h; Inert atmosphere;74%
37076-71-4

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

862508-03-0

N4-(n-pentyloxycarbonyl)-5-fluorocytosine

162204-20-8

N1-(2',3'-di-O-acetyl-5'-deoxy-β-D-ribofuranosyl)-5-fluoro-N4-(pentyloxycarbonyl)cytosine

Conditions
ConditionsYield
Stage #1: 5-deoxy-1,2,3-tri-O-acetyl-D-ribofuranose; N4-(n-pentyloxycarbonyl)-5-fluorocytosine In acetonitrile Inert atmosphere;
Stage #2: With chloro-trimethyl-silane; 1,1,1,3,3,3-hexamethyl-disilazane In acetonitrile at 20℃; for 0.5h;
Stage #3: With trimethylsilyl trifluoromethanesulfonate In acetonitrile at -78 - 20℃;
28%
162204-20-8

N1-(2',3'-di-O-acetyl-5'-deoxy-β-D-ribofuranosyl)-5-fluoro-N4-(pentyloxycarbonyl)cytosine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: HMDS / toluene / 3 h / 100 °C
1.2: 76 percent / SnCl4 / CH2Cl2 / 2 h / 20 °C
2.1: 1311 g / pyridine / CH2Cl2 / -20 - 20 °C
View Scheme
Multi-step reaction with 2 steps
1: tin(IV) chloride / dichloromethane / 5 - 10 °C
2: pyridine / dichloromethane / -5 - 5 °C
View Scheme
1071455-34-9

pentyl (5-fluoro-2-((trimethylsilyl)oxy)pyrimidin-4-yl)carbamate

162204-20-8

N1-(2',3'-di-O-acetyl-5'-deoxy-β-D-ribofuranosyl)-5-fluoro-N4-(pentyloxycarbonyl)cytosine

Conditions
ConditionsYield
With 2,6-di-tert-butyl-4-methylpyridinium trifluoromethanesulfonate In acetonitrile at 140℃;
638-41-5

pentyl chloroformate

162204-20-8

N1-(2',3'-di-O-acetyl-5'-deoxy-β-D-ribofuranosyl)-5-fluoro-N4-(pentyloxycarbonyl)cytosine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: pyridine
2: acetonitrile / 0.5 h / 75 °C
3: 2,6-di-tert-butyl-4-methylpyridinium trifluoromethanesulfonate / acetonitrile / 140 °C
View Scheme
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
Multi-step reaction with 5 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: lithium iodide / acetone / 6 h / Reflux
5: 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride / tetrahydrofuran / 4 h / 20 °C / Inert atmosphere
View Scheme
638-41-5

pentyl chloroformate

41108-04-7

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

162204-20-8

N1-(2',3'-di-O-acetyl-5'-deoxy-β-D-ribofuranosyl)-5-fluoro-N4-(pentyloxycarbonyl)cytosine

Conditions
ConditionsYield
With 2,6-di-tert-butyl-4-methylpyridinium trifluoromethanesulfonate In acetonitrile at 130℃;
128963-10-0

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

162204-20-8

N1-(2',3'-di-O-acetyl-5'-deoxy-β-D-ribofuranosyl)-5-fluoro-N4-(pentyloxycarbonyl)cytosine

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
Multi-step reaction with 5 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
5: dichloromethane
View Scheme
Multi-step reaction with 5 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: lithium iodide / acetone / 6 h / Reflux
5: 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride / tetrahydrofuran / 4 h / 20 °C / Inert atmosphere
View Scheme
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Specification

The 5'-Deoxy-5-fluoro-N-[(pentyloxy)carbonyl]cytidine 2',3'-diacetate, with the CAS registry number 162204-20-8, is also known as Cytidine, 5'-deoxy-5-fluoro-N-[(pentyloxy)carbonyl]-, 2',3'-diacetate. This chemical's molecular formula is C19H26FN3O8 and molecular weight is C19H26FN3O8. Its systematic name is called cytidine, 5'-deoxy-5-fluoro-N-[(pentyloxy)carbonyl]-, 2',3'-diacetate.

Physical properties of 5'-Deoxy-5-fluoro-N-[(pentyloxy)carbonyl]cytidine 2',3'-diacetate: (1)ACD/LogP: 2.14; (2)# of Rule of 5 Violations: 1; (3)ACD/LogD (pH 5.5): 1.77; (4)ACD/LogD (pH 7.4): 0.41; (5)ACD/BCF (pH 5.5): 10.56; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 147.47; (8)ACD/KOC (pH 7.4): 6.56; (9)#H bond acceptors: 11; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 10; (12)Index of Refraction: 1.566; (13)Molar Refractivity: 103.17 cm3; (14)Molar Volume: 315.9 cm3; (15)Surface Tension: 45.7 dyne/cm; (16)Density: 1.4 g/cm3.

You can still convert the following datas into molecular structure:
(1)SMILES: CCCCCOC(=O)Nc1c(cn(c(=O)n1)[C@H]2[C@@H]([C@@H]([C@H](O2)C)OC(=O)C)OC(=O)C)F
(2)InChI: InChI=1/C19H26FN3O8/c1-5-6-7-8-28-19(27)22-16-13(20)9-23(18(26)21-16)17-15(31-12(4)25)14(10(2)29-17)30-11(3)24/h9-10,14-15,17H,5-8H2,1-4H3,(H,21,22,26,27)/t10-,14-,15-,17-/m1/s1
(3)InChIKey: WMJHGZFQHPCWQZ-GWBBYGMBBC