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

Name
2',3'-Di-O-acetyl-5'-deoxy-5-fuluro-D-cytidine
EINECS 605-260-4
CAS No. 161599-46-8
Article Data22
CAS DataBase
Density 1.57 g/cm³
Solubility
Melting Point 196-198?C
Formula C₁₃H₁₆FN₃O₆
Boiling Point 427.4 °C at 760 mmHg
Molecular Weight 329.285
Flash Point 212.3 °C
Transport Information
Appearance WHITE
Safety 24/25
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms 5'-Deoxy-2',3'-di-O-acetyl-5-fluorocytidine;
PSA 122.74000
LogP 0.32650

Synthetic route

: 2022-85-7
Flucytosine

: 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

: 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

Conditions	Yield
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

Conditions	Yield
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

: 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

: 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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

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

: 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

Conditions	Yield
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

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

Conditions	Yield
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

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

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

Conditions

Conditions	Yield
With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride In tetrahydrofuran Reflux; Overall yield = 45 %;

: 4137-56-8
methyl 2,3-O-isopropylidene-5-O-p-tolylsulfonyl-β-D-ribofuranoside

: 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

Conditions	Yield
Multi-step reaction with 4 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 View Scheme
Multi-step reaction with 3 steps 1.1: sodium tetrahydroborate; acetic acid / dimethyl sulfoxide / 20 h / 80 - 85 °C 2.1: sulfuric acid / 17 h / 80 - 90 °C 2.2: 16 h / 20 °C 3.1: 1,1,1,3,3,3-hexamethyl-disilazane / toluene / 100 °C 3.2: 2.33 h / 20 °C / Cooling with ice View Scheme

: 23202-81-5
methyl 5-deoxy-2,3-O-isopropylidene-β-D-ribofuranoside

: 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

Conditions	Yield
Multi-step reaction with 3 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 View Scheme
Multi-step reaction with 2 steps 1.1: sulfuric acid / 17 h / 80 - 90 °C 1.2: 16 h / 20 °C 2.1: 1,1,1,3,3,3-hexamethyl-disilazane / toluene / 100 °C 2.2: 2.33 h / 20 °C / Cooling with ice View Scheme

: 279673-09-5
(2R,3R,4S,5R)-5-methyltetrahydrofuran-2,3,4-triol

: 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

Conditions	Yield
Multi-step reaction with 2 steps 1: triethylamine; dmap / 4 h / -5 - 5 °C / Large scale 2: tin(IV) chloride / dichloromethane / 5 - 10 °C View Scheme

: 111878-21-8
2-trimethylsilyloxy-4-trimethylsilylamino-5-fluoropyrimidine

: 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

: 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

Conditions	Yield
With tin(IV) chloride In dichloromethane at 5 - 10℃;
With tin(IV) chloride In dichloromethane at -1 - 10℃; Temperature; Inert atmosphere;	31 g

: 36468-53-8
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

Conditions	Yield
Multi-step reaction with 6 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 View Scheme
Multi-step reaction with 5 steps 1.1: sulfuric acid; tin(II) chloride dihdyrate / 40 - 45 °C 2.1: pyridine / dichloromethane / 20 h / 0 - 5 °C 3.1: sodium tetrahydroborate; acetic acid / dimethyl sulfoxide / 20 h / 80 - 85 °C 4.1: sulfuric acid / 17 h / 80 - 90 °C 4.2: 16 h / 20 °C 5.1: 1,1,1,3,3,3-hexamethyl-disilazane / toluene / 100 °C 5.2: 2.33 h / 20 °C / Cooling with ice View Scheme

: 4099-85-8
((3aR,4R,6R,6aR)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methanol

: 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

Conditions	Yield
Multi-step reaction with 5 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 View Scheme
Multi-step reaction with 4 steps 1.1: pyridine / dichloromethane / 20 h / 0 - 5 °C 2.1: sodium tetrahydroborate; acetic acid / dimethyl sulfoxide / 20 h / 80 - 85 °C 3.1: sulfuric acid / 17 h / 80 - 90 °C 3.2: 16 h / 20 °C 4.1: 1,1,1,3,3,3-hexamethyl-disilazane / toluene / 100 °C 4.2: 2.33 h / 20 °C / Cooling with ice View Scheme

: 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

: 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

Conditions	Yield
Multi-step reaction with 4 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 View Scheme

: 50600-40-3
(3aS,4S,6aR)-4-(iodomethyl)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxole

: 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

Conditions	Yield
Multi-step reaction with 3 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 View Scheme
Multi-step reaction with 4 steps 1: hydrogen; triethylamine / palladium on activated charcoal / methanol / 24 h / 20 °C / Inert atmosphere 2: hydrogenchloride; water / 2 h / Reflux 3: pyridine / 24 h / 20 °C 4: tin(IV) chloride / dichloromethane / 2 h / 0 °C View Scheme

: 78341-97-6
1-O-methyl-2,3-O-isopropylidene-5-deoxy-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

Conditions	Yield
Multi-step reaction with 2 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 View Scheme
Multi-step reaction with 3 steps 1: hydrogenchloride; water / 2 h / Reflux 2: pyridine / 24 h / 20 °C 3: tin(IV) chloride / dichloromethane / 2 h / 0 °C View Scheme

: 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

: 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

Conditions	Yield
Multi-step reaction with 6 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 View Scheme
Multi-step reaction with 7 steps 1: hydrogenchloride / water / 2 h / Reflux 2: pyridine / 18 h / 20 °C 3: sodium iodide / butanone / 24 h / Reflux 4: hydrogen; triethylamine / palladium on activated charcoal / methanol / 24 h / 20 °C / Inert atmosphere 5: hydrogenchloride; water / 2 h / Reflux 6: pyridine / 24 h / 20 °C 7: tin(IV) chloride / dichloromethane / 2 h / 0 °C View Scheme

Yield

Multi-step reaction with 6 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
View Scheme

Multi-step reaction with 7 steps
1: hydrogenchloride / water / 2 h / Reflux
2: pyridine / 18 h / 20 °C
3: sodium iodide / butanone / 24 h / Reflux
4: hydrogen; triethylamine / palladium on activated charcoal / methanol / 24 h / 20 °C / Inert atmosphere
5: hydrogenchloride; water / 2 h / Reflux
6: pyridine / 24 h / 20 °C
7: tin(IV) chloride / dichloromethane / 2 h / 0 °C
View Scheme

: 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

: 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

Conditions	Yield
Multi-step reaction with 5 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 View Scheme
Multi-step reaction with 6 steps 1: pyridine / 18 h / 20 °C 2: sodium iodide / butanone / 24 h / Reflux 3: hydrogen; triethylamine / palladium on activated charcoal / methanol / 24 h / 20 °C / Inert atmosphere 4: hydrogenchloride; water / 2 h / Reflux 5: pyridine / 24 h / 20 °C 6: tin(IV) chloride / dichloromethane / 2 h / 0 °C View Scheme

Yield

Multi-step reaction with 5 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
View Scheme

Multi-step reaction with 6 steps
1: pyridine / 18 h / 20 °C
2: sodium iodide / butanone / 24 h / Reflux
3: hydrogen; triethylamine / palladium on activated charcoal / methanol / 24 h / 20 °C / Inert atmosphere
4: hydrogenchloride; water / 2 h / Reflux
5: pyridine / 24 h / 20 °C
6: tin(IV) chloride / dichloromethane / 2 h / 0 °C
View Scheme

: 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

: 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

Conditions	Yield
Multi-step reaction with 4 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 View Scheme
Multi-step reaction with 5 steps 1: sodium iodide / butanone / 24 h / Reflux 2: hydrogen; triethylamine / palladium on activated charcoal / methanol / 24 h / 20 °C / Inert atmosphere 3: hydrogenchloride; water / 2 h / Reflux 4: pyridine / 24 h / 20 °C 5: tin(IV) chloride / dichloromethane / 2 h / 0 °C View Scheme

: 158112-55-1
5-O-deoxy-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

Conditions	Yield
Multi-step reaction with 2 steps 1: pyridine / 24 h / 20 °C 2: tin(IV) chloride / dichloromethane / 2 h / 0 °C View Scheme

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

: 66335-38-4
5'-deoxy-5-fluorocytidine

Conditions

Conditions	Yield
With ammonia In methanol; water at 45 - 55℃; Product distribution / selectivity;	95%
With methanol; diethylamine at 20 - 50℃; for 2h; Inert atmosphere;	80%
With methanol; diethylamine at 55℃; for 2h;

: 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

Conditions	Yield
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%

: 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

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

...Expand

: 1,3-thiazolone formyl chloride

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

: C17H19FN4O8S

Conditions

Conditions	Yield
With pyridine In dichloromethane at -15 - 20℃; for 2h;	85%

: 3,7,11,15-tetramethyl-hexadecyl 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

: 2’,3’-di-O-acetyl-5’-deoxy-5-fluoro-N4-(3,7,11,15-tetramethylhexadecyloxycarbonyl)cytidine

Conditions

Conditions	Yield
With pyridine In dichloromethane at 20℃;	84.1%

CH2 Cl: CH2 Cl

: 20412-38-8
neopentyl 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

: 162204-44-6
5'-deoxy-5-fluoro-N4-(neopentyloxycarbonyl)-cytidine

Conditions

Conditions	Yield
With pyridine; sodium hydroxide; sodium carbonate In methanol; ethanol; dichloromethane	84%

...Expand

: 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

: 154361-50-9
capecitabine

Conditions

Conditions	Yield
With sodium hydroxide In water; acetone at 30℃; for 5h; Green chemistry;	82%
Stage #1: pentyl chloroformate; (2R,3R,4R,5R)-2-(4-amino-5-fluoro-2-oxopyrimidin-1(2H)-yl)-5-methyl-tetrahydrofuran-3,4-diyl diacetate With pyridine In dichloromethane at 0℃; for 1h; Stage #2: With sodium hydroxide In ethanol; water at -5 - 0℃; for 0.233333h;	80.2%
Multi-step reaction with 2 steps 1: dichloromethane 2: sodium hydroxide / methanol View Scheme
Multi-step reaction with 2 steps 1: pyridine / dichloromethane / 1 h / 0 °C 2: sodium methylate / methanol / 1 h / 20 °C View Scheme
Multi-step reaction with 2 steps 1: potassium phosphate / isopropyl alcohol; dichloromethane / 4 h / 0 - 25 °C / Inert atmosphere 2: sodium hydroxide / methanol; water / 1 h / -10 - 5 °C / Autoclave View Scheme

: 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

: C27H42FN3O10

Conditions

Conditions	Yield
With sodium hydroxide In water; acetone at 30℃; for 1h; Flow reactor;	35%

: 6092-54-2
n-hexyl 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

: 162204-21-9
Acetic acid (2R,3R,4R,5R)-4-acetoxy-2-(5-fluoro-4-hexyloxycarbonylamino-2-oxo-2H-pyrimidin-1-yl)-5-methyl-tetrahydro-furan-3-yl ester

Conditions

Conditions	Yield
With pyridine In dichloromethane at -20 - 20℃; Acylation;

: 33758-34-8
n-heptyl 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

: Acetic acid (2R,3R,4R,5R)-4-acetoxy-2-(5-fluoro-4-heptyloxycarbonylamino-2-oxo-2H-pyrimidin-1-yl)-5-methyl-tetrahydro-furan-3-yl ester

Conditions

Conditions	Yield
With pyridine In dichloromethane at -20 - 20℃; Acylation;

: 7452-59-7
octyl 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

: 161599-33-3
Acetic acid (2R,3R,4R,5R)-4-acetoxy-2-(5-fluoro-4-octyloxycarbonylamino-2-oxo-2H-pyrimidin-1-yl)-5-methyl-tetrahydro-furan-3-yl ester

Conditions

Conditions	Yield
With pyridine In dichloromethane at -20 - 20℃; Acylation;

: 57045-82-6
chloroformic acid n-nonyl ester

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

: Acetic acid (2R,3R,4R,5R)-4-acetoxy-2-(5-fluoro-4-nonyloxycarbonylamino-2-oxo-2H-pyrimidin-1-yl)-5-methyl-tetrahydro-furan-3-yl ester

Conditions

Conditions	Yield
With pyridine In dichloromethane at -20 - 20℃; Acylation;

: 2905-62-6
3,5-dichlorobenzoyl chloride

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

: Acetic acid (2R,3R,4R,5R)-4-acetoxy-2-[4-(3,5-dichloro-benzoylamino)-5-fluoro-2-oxo-2H-pyrimidin-1-yl]-5-methyl-tetrahydro-furan-3-yl ester

Conditions

Conditions	Yield
With pyridine In dichloromethane at -20 - 20℃; Acylation;

: 541-41-3
chloroformic acid ethyl ester

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

: Acetic acid (2R,3R,4R,5R)-4-acetoxy-2-(4-ethoxycarbonylamino-5-fluoro-2-oxo-2H-pyrimidin-1-yl)-5-methyl-tetrahydro-furan-3-yl ester

Conditions

Conditions	Yield
With pyridine In dichloromethane at -20 - 20℃; Acylation;

: 4521-61-3
3,4,5-Trimethoxybenzoyl chloride

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

: 161599-31-1
Acetic acid (2R,3R,4R,5R)-4-acetoxy-2-[5-fluoro-2-oxo-4-(3,4,5-trimethoxy-benzoylamino)-2H-pyrimidin-1-yl]-5-methyl-tetrahydro-furan-3-yl ester

Conditions

Conditions	Yield
With pyridine In dichloromethane at -20 - 20℃; Acylation;

: 17213-57-9
3,5-dimethoxybenzoyl chloride

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

: Acetic acid (2R,3R,4R,5R)-4-acetoxy-2-[4-(3,5-dimethoxy-benzoylamino)-5-fluoro-2-oxo-2H-pyrimidin-1-yl]-5-methyl-tetrahydro-furan-3-yl ester

Conditions

Conditions	Yield
With pyridine In dichloromethane at -20 - 20℃; Acylation;

: 79-22-1
methyl 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

: Acetic acid (2R,3R,4R,5R)-4-acetoxy-2-(5-fluoro-4-methoxycarbonylamino-2-oxo-2H-pyrimidin-1-yl)-5-methyl-tetrahydro-furan-3-yl ester

Conditions

Conditions	Yield
With pyridine In dichloromethane at -20 - 20℃; Acylation;

: 592-34-7
carbonochloridic acid, butyl ester

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

: 162204-19-5
Acetic acid (2R,3R,4R,5R)-4-acetoxy-2-(4-butoxycarbonylamino-5-fluoro-2-oxo-2H-pyrimidin-1-yl)-5-methyl-tetrahydro-furan-3-yl ester

Conditions

Conditions	Yield
With pyridine In dichloromethane at -20 - 20℃; Acylation;

: 6613-44-1
3,5-dimethylbenzoyl chloride

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

: Acetic acid (2R,3R,4R,5R)-4-acetoxy-2-[4-(3,5-dimethyl-benzoylamino)-5-fluoro-2-oxo-2H-pyrimidin-1-yl]-5-methyl-tetrahydro-furan-3-yl ester

Conditions

Conditions	Yield
With pyridine In dichloromethane at -20 - 20℃; Acylation;

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

: 109-61-5
propoxycarbonyl chloride

: 162204-18-4
Acetic acid (2R,3R,4R,5R)-4-acetoxy-2-(5-fluoro-2-oxo-4-propoxycarbonylamino-2H-pyrimidin-1-yl)-5-methyl-tetrahydro-furan-3-yl ester

Conditions

Conditions	Yield
With pyridine In dichloromethane at -20 - 20℃; Acylation;

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

: 124012-42-6
5'-deoxy-5-fluoro-N4-(3,4,5-trimethoxybenzoyl)cytidine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: pyridine / CH2Cl2 / -20 - 20 °C 2: NaOH / methanol; H2O / -20 - -5 °C View Scheme

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

: 5'-deoxy-5-fluoro-N4-(methoxycarbonyl)cytidine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: pyridine / CH2Cl2 / -20 - 20 °C 2: NaOH / methanol; H2O / -20 - -5 °C View Scheme

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

: 5'-deoxy-5-fluoro-N4-(ethoxycarbonyl)cytidine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: pyridine / CH2Cl2 / -20 - 20 °C 2: NaOH / methanol; H2O / -20 - -5 °C View Scheme

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

: 5'-deoxy-5-fluoro-N4-(propoxycarbonyl)cytidine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: pyridine / CH2Cl2 / -20 - 20 °C 2: NaOH / methanol; H2O / -20 - -5 °C View Scheme

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

: 5'-deoxy-5-fluoro-N4-(butoxycarbonyl)cytidine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: pyridine / CH2Cl2 / -20 - 20 °C 2: NaOH / methanol; H2O / -20 - -5 °C View Scheme

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

: 154361-50-9
capecitabine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 1311 g / pyridine / CH2Cl2 / -20 - 20 °C 2: 170 g / NaOH / methanol; H2O / -20 - -5 °C View Scheme
Multi-step reaction with 2 steps 1: potassium carbonate / acetone / 20 - 30 °C / Inert atmosphere 2: sodium hydroxide / acetone / 2 h / -15 - 10 °C 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

Product Name

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

Synthetic route

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

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