Product Name

  • Name

    5`-deoxy-5-fluore-N-[(pentoyloxy)carbonyl]cytidine 2`,3`-diacetate

  • EINECS 700-593-2
  • CAS No. 162204-20-8
  • Article Data21
  • CAS DataBase
  • Density 1.4 g/cm3
  • Solubility
  • Melting Point 100-102?C
  • Formula C19H26FN3O8
  • Boiling Point
  • Molecular Weight 443.429
  • Flash Point
  • Transport Information
  • Appearance Powder
  • Safety 24/25
  • Risk Codes
  • Molecular Structure Molecular Structure of 162204-20-8 (5`-deoxy-5-fluore-N-[(pentoyloxy)carbonyl]cytidine 2`,3`-diacetate)
  • Hazard Symbols
  • 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;
  • PSA 135.05000
  • LogP 1.97480

Synthetic route

pentyl chloroformate
638-41-5

pentyl chloroformate

(2R,3R,4R,5R)-2-(4-amino-5-fluoro-2-oxopyrimidin-1(2H)-yl)-5-methyl-tetrahydrofuran-3,4-diyl diacetate
161599-46-8

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

N1-(2',3'-di-O-acetyl-5'-deoxy-β-D-ribofuranosyl)-5-fluoro-N4-(pentyloxycarbonyl)cytosine
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%
(5-fluoro-2-oxo-1,2-dihydropyrimidin-4-yl)carbamic acid amyl ester
862508-03-0

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

C24H24O7

C24H24O7

N1-(2',3'-di-O-acetyl-5'-deoxy-β-D-ribofuranosyl)-5-fluoro-N4-(pentyloxycarbonyl)cytosine
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%
pentan-1-ol
71-41-0

pentan-1-ol

1,1'-carbonyldiimidazole
530-62-1

1,1'-carbonyldiimidazole

(2R,3R,4R,5R)-2-(4-amino-5-fluoro-2-oxopyrimidin-1(2H)-yl)-5-methyl-tetrahydrofuran-3,4-diyl diacetate
161599-46-8

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

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

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

N1-(2',3'-di-O-acetyl-5'-deoxy-β-D-ribofuranosyl)-5-fluoro-N4-(pentyloxycarbonyl)cytosine
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%
5-deoxy-1,2,3-tri-O-acetyl-D-ribofuranose
37076-71-4

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

N4-(n-pentyloxycarbonyl)-5-fluorocytosine
862508-03-0

N4-(n-pentyloxycarbonyl)-5-fluorocytosine

N1-(2',3'-di-O-acetyl-5'-deoxy-β-D-ribofuranosyl)-5-fluoro-N4-(pentyloxycarbonyl)cytosine
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%
1,2,3-tri-O-acetyl-5-deoxy-β-D-ribofuranose
27821-07-4, 27930-18-3, 37076-71-4, 62211-93-2, 63903-44-6, 76497-54-6

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

N1-(2',3'-di-O-acetyl-5'-deoxy-β-D-ribofuranosyl)-5-fluoro-N4-(pentyloxycarbonyl)cytosine
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
pentyl (5-fluoro-2-((trimethylsilyl)oxy)pyrimidin-4-yl)carbamate
1071455-34-9

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

1,2,3-tri-O-acetyl-5-deoxy-β-D-ribofuranose
27821-07-4, 27930-18-3, 37076-71-4, 62211-93-2, 63903-44-6, 76497-54-6

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

N1-(2',3'-di-O-acetyl-5'-deoxy-β-D-ribofuranosyl)-5-fluoro-N4-(pentyloxycarbonyl)cytosine
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℃;
pentyl chloroformate
638-41-5

pentyl chloroformate

N1-(2',3'-di-O-acetyl-5'-deoxy-β-D-ribofuranosyl)-5-fluoro-N4-(pentyloxycarbonyl)cytosine
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
pentyl chloroformate
638-41-5

pentyl chloroformate

5-fluoro-2-trimethylsilanyloxy-pyrimidin-4-ylamine
41108-04-7

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

1,2,3-tri-O-acetyl-5-deoxy-β-D-ribofuranose
27821-07-4, 27930-18-3, 37076-71-4, 62211-93-2, 63903-44-6, 76497-54-6

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

N1-(2',3'-di-O-acetyl-5'-deoxy-β-D-ribofuranosyl)-5-fluoro-N4-(pentyloxycarbonyl)cytosine
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℃;
...Expand
2',3',5'-tri-O-acetyl-5-fluorocytidine
128963-10-0

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

N1-(2',3'-di-O-acetyl-5'-deoxy-β-D-ribofuranosyl)-5-fluoro-N4-(pentyloxycarbonyl)cytosine
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
N1-(2',3',5'-tri-O-acetyl-β-D-ribofuranosyl)-5-fluoro-N4-(n-pentyloxycarbonyl)cytosine
396684-34-7

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

N1-(2',3'-di-O-acetyl-5'-deoxy-β-D-ribofuranosyl)-5-fluoro-N4-(pentyloxycarbonyl)cytosine
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: alcalase enzyme cross linked aggregate / ethanol / 100 h / 20 °C / Enzymatic reaction
2: carbon tetrabromide / dichloromethane / 3 h / 20 °C / Inert atmosphere
3: 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride / tetrahydrofuran / Reflux
View Scheme
Multi-step reaction with 4 steps
1: alcalase enzyme cross linked aggregate / ethanol / 100 h / 20 °C / Enzymatic reaction
2: carbon tetrabromide / dichloromethane / 3 h / 20 °C / Inert atmosphere
3: 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride / tetrahydrofuran / Reflux
4: dichloromethane
View Scheme
Multi-step reaction with 4 steps
1: alcalase enzyme cross linked aggregate / ethanol / 100 h / 20 °C / Enzymatic reaction
2: carbon tetrabromide / dichloromethane / 3 h / 20 °C / Inert atmosphere
3: lithium iodide / acetone / 6 h / Reflux
4: 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride / tetrahydrofuran / 4 h / 20 °C / Inert atmosphere
View Scheme
2',3'-di-O-acetyl-5-fluoro-N4-(pentyloxycarbonyl)cytidine

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

N1-(2',3'-di-O-acetyl-5'-deoxy-β-D-ribofuranosyl)-5-fluoro-N4-(pentyloxycarbonyl)cytosine
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: carbon tetrabromide / dichloromethane / 3 h / 20 °C / Inert atmosphere
2: 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride / tetrahydrofuran / Reflux
View Scheme
Multi-step reaction with 3 steps
1: carbon tetrabromide / dichloromethane / 3 h / 20 °C / Inert atmosphere
2: 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride / tetrahydrofuran / Reflux
3: dichloromethane
View Scheme
Multi-step reaction with 3 steps
1: carbon tetrabromide / dichloromethane / 3 h / 20 °C / Inert atmosphere
2: lithium iodide / acetone / 6 h / Reflux
3: 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride / tetrahydrofuran / 4 h / 20 °C / Inert atmosphere
View Scheme
5'-bromo-2',3'-di-O-acetyl-5-fluoro-N4-(pentyloxycarbonyl)cytidine

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

A

(2R,3R,4R,5R)-2-(4-amino-5-fluoro-2-oxopyrimidin-1(2H)-yl)-5-methyl-tetrahydrofuran-3,4-diyl diacetate
161599-46-8

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

B

N1-(2',3'-di-O-acetyl-5'-deoxy-β-D-ribofuranosyl)-5-fluoro-N4-(pentyloxycarbonyl)cytosine
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 Reflux; Overall yield = 45 %;
5'-bromo-2',3'-di-O-acetyl-5-fluoro-N4-(pentyloxycarbonyl)cytidine

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

N1-(2',3'-di-O-acetyl-5'-deoxy-β-D-ribofuranosyl)-5-fluoro-N4-(pentyloxycarbonyl)cytosine
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: lithium iodide / acetone / 6 h / Reflux
2: 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride / tetrahydrofuran / 4 h / 20 °C / Inert atmosphere
View Scheme
Multi-step reaction with 2 steps
1: 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride / tetrahydrofuran / Reflux
2: dichloromethane
View Scheme
methyl 2,3-O-isopropylidene-5-O-p-tolylsulfonyl-β-D-ribofuranoside
4137-56-8

methyl 2,3-O-isopropylidene-5-O-p-tolylsulfonyl-β-D-ribofuranoside

N1-(2',3'-di-O-acetyl-5'-deoxy-β-D-ribofuranosyl)-5-fluoro-N4-(pentyloxycarbonyl)cytosine
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 5 steps
1: sodium tetrahydroborate / dimethyl sulfoxide
2: sulfuric acid / water / 80 - 90 °C / Large scale
3: triethylamine; dmap / 4 h / -5 - 5 °C / Large scale
4: tin(IV) chloride / dichloromethane / 5 - 10 °C
5: pyridine / dichloromethane / -5 - 5 °C
View Scheme
methyl 5-deoxy-2,3-O-isopropylidene-β-D-ribofuranoside
23202-81-5

methyl 5-deoxy-2,3-O-isopropylidene-β-D-ribofuranoside

N1-(2',3'-di-O-acetyl-5'-deoxy-β-D-ribofuranosyl)-5-fluoro-N4-(pentyloxycarbonyl)cytosine
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: sulfuric acid / water / 80 - 90 °C / Large scale
2: triethylamine; dmap / 4 h / -5 - 5 °C / Large scale
3: tin(IV) chloride / dichloromethane / 5 - 10 °C
4: pyridine / dichloromethane / -5 - 5 °C
View Scheme
(2R,3R,4S,5R)-5-methyltetrahydrofuran-2,3,4-triol
279673-09-5

(2R,3R,4S,5R)-5-methyltetrahydrofuran-2,3,4-triol

N1-(2',3'-di-O-acetyl-5'-deoxy-β-D-ribofuranosyl)-5-fluoro-N4-(pentyloxycarbonyl)cytosine
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: triethylamine; dmap / 4 h / -5 - 5 °C / Large scale
2: tin(IV) chloride / dichloromethane / 5 - 10 °C
3: pyridine / dichloromethane / -5 - 5 °C
View Scheme
β-D-ribofuranose
36468-53-8

β-D-ribofuranose

N1-(2',3'-di-O-acetyl-5'-deoxy-β-D-ribofuranosyl)-5-fluoro-N4-(pentyloxycarbonyl)cytosine
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 7 steps
1: sulfuric acid / 0 - 20 °C
2: triethylamine / dichloromethane / 0 - 20 °C
3: sodium tetrahydroborate; lithium chloride / diethylene glycol dimethyl ether / 20 h / 80 - 90 °C
4: sulfuric acid / water / 80 - 90 °C / Large scale
5: triethylamine; dmap / 4 h / -5 - 5 °C / Large scale
6: tin(IV) chloride / dichloromethane / 5 - 10 °C
7: pyridine / dichloromethane / -5 - 5 °C
View Scheme
((3aR,4R,6R,6aR)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methanol
4099-85-8

((3aR,4R,6R,6aR)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methanol

N1-(2',3'-di-O-acetyl-5'-deoxy-β-D-ribofuranosyl)-5-fluoro-N4-(pentyloxycarbonyl)cytosine
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 6 steps
1: triethylamine / dichloromethane / 0 - 20 °C
2: sodium tetrahydroborate; lithium chloride / diethylene glycol dimethyl ether / 20 h / 80 - 90 °C
3: sulfuric acid / water / 80 - 90 °C / Large scale
4: triethylamine; dmap / 4 h / -5 - 5 °C / Large scale
5: tin(IV) chloride / dichloromethane / 5 - 10 °C
6: pyridine / dichloromethane / -5 - 5 °C
View Scheme
1-O-methyl-2,3-O-isopropylidene-5-O-(methanesulfonyl)-β-D-ribofuranoside
50610-99-6, 75100-24-2, 81026-76-8, 96896-28-5

1-O-methyl-2,3-O-isopropylidene-5-O-(methanesulfonyl)-β-D-ribofuranoside

N1-(2',3'-di-O-acetyl-5'-deoxy-β-D-ribofuranosyl)-5-fluoro-N4-(pentyloxycarbonyl)cytosine
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 5 steps
1: sodium tetrahydroborate; lithium chloride / diethylene glycol dimethyl ether / 20 h / 80 - 90 °C
2: sulfuric acid / water / 80 - 90 °C / Large scale
3: triethylamine; dmap / 4 h / -5 - 5 °C / Large scale
4: tin(IV) chloride / dichloromethane / 5 - 10 °C
5: pyridine / dichloromethane / -5 - 5 °C
View Scheme
5-deoxy-1,2,3-tri-O-acetyl-D-ribofuranose
37076-71-4

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

N1-(2',3'-di-O-acetyl-5'-deoxy-β-D-ribofuranosyl)-5-fluoro-N4-(pentyloxycarbonyl)cytosine
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: 1,1,1,3,3,3-hexamethyl-disilazane / toluene / 4 h / Autoclave; Reflux; Industrial scale
1.2: 12 h / 2 - 20 °C / Industrial scale
2.1: pyridine / dichloromethane / -15 - -5 °C / Industrial scale
View Scheme
(3aS,4S,6aR)-4-(iodomethyl)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxole
50600-40-3

(3aS,4S,6aR)-4-(iodomethyl)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxole

N1-(2',3'-di-O-acetyl-5'-deoxy-β-D-ribofuranosyl)-5-fluoro-N4-(pentyloxycarbonyl)cytosine
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
1.1: 1-ethylpiperidine hypophosphite; di-isopropyl azodicarboxylate; triethylamine / 1,4-dioxane / Reflux; Inert atmosphere
2.1: sulfuric acid / water / 2 h / Reflux
2.2: 20 h / 20 °C
3.1: tin(IV) chloride; sodium hydrogencarbonate / water; dichloromethane / 0.5 h / 0 - 20 °C
4.1: pyridine / dichloromethane / 1 h / 0 °C
View Scheme
1-O-methyl-2,3-O-isopropylidene-5-deoxy-D-ribofuranose
78341-97-6

1-O-methyl-2,3-O-isopropylidene-5-deoxy-D-ribofuranose

N1-(2',3'-di-O-acetyl-5'-deoxy-β-D-ribofuranosyl)-5-fluoro-N4-(pentyloxycarbonyl)cytosine
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
1.1: sulfuric acid / water / 2 h / Reflux
1.2: 20 h / 20 °C
2.1: tin(IV) chloride; sodium hydrogencarbonate / water; dichloromethane / 0.5 h / 0 - 20 °C
3.1: pyridine / dichloromethane / 1 h / 0 °C
View Scheme
D-Ribose
532-20-7, 613-83-2, 7261-25-8, 7687-39-0, 13221-22-2, 14795-83-6, 15761-67-8, 20074-49-1, 25545-03-3, 25545-04-4, 32445-75-3, 34436-17-4, 36441-93-7, 36468-53-8, 37110-85-3, 37388-49-1, 38029-69-5, 40461-77-6, 40461-89-0, 41546-19-4, 41546-20-7, 41546-21-8, 41546-26-3, 41546-29-6, 41546-30-9, 41546-31-0, 126872-16-0, 131064-98-7

D-Ribose

N1-(2',3'-di-O-acetyl-5'-deoxy-β-D-ribofuranosyl)-5-fluoro-N4-(pentyloxycarbonyl)cytosine
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 7 steps
1.1: hydrogenchloride / water / 3 h / Reflux
2.1: triethylamine / dichloromethane / 4 h / 0 - 5 °C
3.1: sodium iodide / acetonitrile / 12 h / Reflux
4.1: 1-ethylpiperidine hypophosphite; di-isopropyl azodicarboxylate; triethylamine / 1,4-dioxane / Reflux; Inert atmosphere
5.1: sulfuric acid / water / 2 h / Reflux
5.2: 20 h / 20 °C
6.1: tin(IV) chloride; sodium hydrogencarbonate / water; dichloromethane / 0.5 h / 0 - 20 °C
7.1: pyridine / dichloromethane / 1 h / 0 °C
View Scheme
methyl 2,3-O-isopropylidene-D-ribofuranoside
4099-85-8, 5531-21-5, 20672-63-3, 20672-65-5, 58763-00-1, 63029-07-2, 72402-14-3, 84894-45-1, 129263-68-9

methyl 2,3-O-isopropylidene-D-ribofuranoside

N1-(2',3'-di-O-acetyl-5'-deoxy-β-D-ribofuranosyl)-5-fluoro-N4-(pentyloxycarbonyl)cytosine
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 6 steps
1.1: triethylamine / dichloromethane / 4 h / 0 - 5 °C
2.1: sodium iodide / acetonitrile / 12 h / Reflux
3.1: 1-ethylpiperidine hypophosphite; di-isopropyl azodicarboxylate; triethylamine / 1,4-dioxane / Reflux; Inert atmosphere
4.1: sulfuric acid / water / 2 h / Reflux
4.2: 20 h / 20 °C
5.1: tin(IV) chloride; sodium hydrogencarbonate / water; dichloromethane / 0.5 h / 0 - 20 °C
6.1: pyridine / dichloromethane / 1 h / 0 °C
View Scheme
((3aR,4R,6aR)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methyl 4-methylbenzenesulfonate
4137-56-8, 5531-22-6, 6953-71-5, 52631-00-2, 63087-95-6, 84894-43-9, 13007-50-6

((3aR,4R,6aR)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methyl 4-methylbenzenesulfonate

N1-(2',3'-di-O-acetyl-5'-deoxy-β-D-ribofuranosyl)-5-fluoro-N4-(pentyloxycarbonyl)cytosine
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 5 steps
1.1: sodium iodide / acetonitrile / 12 h / Reflux
2.1: 1-ethylpiperidine hypophosphite; di-isopropyl azodicarboxylate; triethylamine / 1,4-dioxane / Reflux; Inert atmosphere
3.1: sulfuric acid / water / 2 h / Reflux
3.2: 20 h / 20 °C
4.1: tin(IV) chloride; sodium hydrogencarbonate / water; dichloromethane / 0.5 h / 0 - 20 °C
5.1: pyridine / dichloromethane / 1 h / 0 °C
View Scheme
5-deoxy-1,2,3-tri-O-acetyl-D-ribofuranose
37076-71-4

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

(5-fluoro-2-oxo-1,2-dihydropyrimidin-4-yl)carbamic acid amyl ester
862508-03-0

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

N1-(2',3'-di-O-acetyl-5'-deoxy-β-D-ribofuranosyl)-5-fluoro-N4-(pentyloxycarbonyl)cytosine
162204-20-8

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

Conditions
ConditionsYield
With boron trifluoride diethyl etherate at 5 - 40℃; for 3h;330.8 g
N1-(2',3'-di-O-acetyl-5'-deoxy-β-D-ribofuranosyl)-5-fluoro-N4-(pentyloxycarbonyl)cytosine
162204-20-8

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

capecitabine
154361-50-9

capecitabine

Conditions
ConditionsYield
Stage #1: N1-(2',3'-di-O-acetyl-5'-deoxy-β-D-ribofuranosyl)-5-fluoro-N4-(pentyloxycarbonyl)cytosine With water; sodium hydroxide In methanol at -15℃;
Stage #2: With hydrogenchloride In methanol; water at -15℃; pH=5;		98%
With potassium hydroxide In methanol at 0 - 15℃; for 1h; Reagent/catalyst;96.1%
With sodium hydroxide In methanol; water at -10 - 5℃; for 1h; Autoclave;87.5%
N1-(2',3'-di-O-acetyl-5'-deoxy-β-D-ribofuranosyl)-5-fluoro-N4-(pentyloxycarbonyl)cytosine
162204-20-8

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

5'-deoxy-5-fluoro-N4-(n-pentyloxycarbonyl)cytidine-2',3'-carbonate
921769-65-5

5'-deoxy-5-fluoro-N4-(n-pentyloxycarbonyl)cytidine-2',3'-carbonate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: sodium hydroxide / acetone / 2 h / -15 - 10 °C
2: dichloromethane / 20 °C / Inert atmosphere
View Scheme
dimethyl sulfate
77-78-1

dimethyl sulfate

N1-(2',3'-di-O-acetyl-5'-deoxy-β-D-ribofuranosyl)-5-fluoro-N4-(pentyloxycarbonyl)cytosine
162204-20-8

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

A

C20H28FN3O8

C20H28FN3O8

B

C20H28FN3O8

C20H28FN3O8

Conditions
ConditionsYield
With triethylamine In 1,2-dichloro-ethane at 50℃;A 0.2 g
B 0.59 g
...Expand

5'-Deoxy-5-fluoro-N-[(pentyloxy)carbonyl]cytidine 2',3'-diacetate 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

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