Product Name

  • Name

    (3R,4R,5R)-3-fluoro-4-hydroxy-5-(hydroxyMethyl)-3-Methyl-dihydrofuran-2(3H)-one

  • EINECS
  • CAS No. 879551-04-9
  • Article Data20
  • CAS DataBase
  • Density 1.42±0.1 g/cm3 (20 oC 760 Torr), Calc.*
  • Solubility Very soluble (1000 g/L) (25 oC), Calc.*
  • Melting Point 142-143 oC (ethyl acetate heptane )**
  • Formula C6H9FO4
  • Boiling Point 352.7±42.0 °C(Predicted)
  • Molecular Weight 164.133
  • Flash Point
  • Transport Information
  • Appearance
  • Safety
  • Risk Codes
  • Molecular Structure Molecular Structure of 879551-04-9 ((3R,4R,5R)-3-fluoro-4-hydroxy-5-(hydroxyMethyl)-3-Methyl-dihydrofuran-2(3H)-one)
  • Hazard Symbols
  • Synonyms (3R,4R,5R)-3-fluoro-4-hydroxy-5-(hydroxyMethyl)-3-Methyl-dihydrofuran-2(3H)-one;(3R,4R,5R)-3-Fluoro-4-hydroxy-5-(hydroxyMethyl)-3-Methyloxolan-2-one;(2R)-2-Deoxy-2-fluoro-2-methyl-D-erythro-pentonic acid gamma-lactone
  • PSA 66.76000
  • LogP -1.00680

Synthetic route

(2R,3R,4R)-2-fluoro-4,5-O-isopropylidene-2-methyl-3-sulfooxy-3,4,5-thydroxypentanoic acid ethyl ester tetrabutylammoniun salt

(2R,3R,4R)-2-fluoro-4,5-O-isopropylidene-2-methyl-3-sulfooxy-3,4,5-thydroxypentanoic acid ethyl ester tetrabutylammoniun salt

(3R,4R,5R)-3‑fluoro‑4‑hydroxy‑5‑(hydroxymethyl)‑3‑methyltetrahydrofuran‑2‑one
879551-04-9

(3R,4R,5R)-3‑fluoro‑4‑hydroxy‑5‑(hydroxymethyl)‑3‑methyltetrahydrofuran‑2‑one

Conditions
ConditionsYield
With trifluoroacetic acid In water; acetonitrile at 80℃; for 1.5h;100%
(S)-3-((2R,3R)-3-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-2-fluoro-3-hydroxy-2-methylpropanoyl)-4-isopropyl-5,5-diphenyloxazolidin-2-one

(S)-3-((2R,3R)-3-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-2-fluoro-3-hydroxy-2-methylpropanoyl)-4-isopropyl-5,5-diphenyloxazolidin-2-one

(3R,4R,5R)-3‑fluoro‑4‑hydroxy‑5‑(hydroxymethyl)‑3‑methyltetrahydrofuran‑2‑one
879551-04-9

(3R,4R,5R)-3‑fluoro‑4‑hydroxy‑5‑(hydroxymethyl)‑3‑methyltetrahydrofuran‑2‑one

Conditions
ConditionsYield
With lithium hydroxide monohydrate; dihydrogen peroxide In tetrahydrofuran; water at 0 - 5℃; for 1h;100%
((2R,3R,4R)-3-benzoyloxy-4-fluoro-4-methyl-5-oxo-tetrahydrofuran-2-yl)methyl benzoate
874638-80-9

((2R,3R,4R)-3-benzoyloxy-4-fluoro-4-methyl-5-oxo-tetrahydrofuran-2-yl)methyl benzoate

(3R,4R,5R)-3‑fluoro‑4‑hydroxy‑5‑(hydroxymethyl)‑3‑methyltetrahydrofuran‑2‑one
879551-04-9

(3R,4R,5R)-3‑fluoro‑4‑hydroxy‑5‑(hydroxymethyl)‑3‑methyltetrahydrofuran‑2‑one

Conditions
ConditionsYield
With methanesulfonic acid In ethanol for 5h; Reagent/catalyst; Solvent; Reflux;95.3%
With sodium methylate In methanol at 20℃; for 2h;
(4S,5R)-ethyl-5-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-4-meth-yl-1,3,2-dioxathiolane-4-carboxylate 2,2-dioxide
879551-01-6

(4S,5R)-ethyl-5-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-4-meth-yl-1,3,2-dioxathiolane-4-carboxylate 2,2-dioxide

(3R,4R,5R)-3‑fluoro‑4‑hydroxy‑5‑(hydroxymethyl)‑3‑methyltetrahydrofuran‑2‑one
879551-04-9

(3R,4R,5R)-3‑fluoro‑4‑hydroxy‑5‑(hydroxymethyl)‑3‑methyltetrahydrofuran‑2‑one

Conditions
ConditionsYield
Stage #1: (4S,5R)-ethyl-5-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-4-meth-yl-1,3,2-dioxathiolane-4-carboxylate 2,2-dioxide With triethylamine tris(hydrogen fluoride) In dichloromethane at 90℃; for 3h;
Stage #2: With hydrogenchloride; barium(II) chloride In dichloromethane at 50℃; for 5h; Solvent; Temperature; Concentration;		89%
Multi-step reaction with 2 steps
1.1: tetraethylammonium fluoride / 1,4-dioxane / 16 h / 120 °C
1.2: 3 h / 20 °C
2.1: water; hydrogenchloride / ethanol / 48 h / 20 °C
View Scheme
Multi-step reaction with 2 steps
1.1: triethylamine tris(hydrogen fluoride) / 2 h / 82 - 85 °C
2.1: hydrogenchloride / 0.5 h / 90 - 92 °C
2.2: 4 h
View Scheme
C11H19FO5

C11H19FO5

(3R,4R,5R)-3‑fluoro‑4‑hydroxy‑5‑(hydroxymethyl)‑3‑methyltetrahydrofuran‑2‑one
879551-04-9

(3R,4R,5R)-3‑fluoro‑4‑hydroxy‑5‑(hydroxymethyl)‑3‑methyltetrahydrofuran‑2‑one

Conditions
ConditionsYield
With hydrogenchloride In ethanol; water at 50℃; for 24h; Reagent/catalyst; Solvent; Temperature; Concentration;88%
2-deoxy-2-fluoro-3,4-O-isopropylidene-2-C-methyI-D-ribono-1,5-lactone

2-deoxy-2-fluoro-3,4-O-isopropylidene-2-C-methyI-D-ribono-1,5-lactone

A

(3R,4R,5R)-3‑fluoro‑4‑hydroxy‑5‑(hydroxymethyl)‑3‑methyltetrahydrofuran‑2‑one
879551-04-9

(3R,4R,5R)-3‑fluoro‑4‑hydroxy‑5‑(hydroxymethyl)‑3‑methyltetrahydrofuran‑2‑one

B

2-deoxy-2-fluoro-2-C-methyI-D-ribono-1,5-lactone

2-deoxy-2-fluoro-2-C-methyI-D-ribono-1,5-lactone

Conditions
ConditionsYield
With trifluoroacetic acid In 1,4-dioxane; water at 20℃; for 48h;A 83%
B 6%
(S)-3-((2R,3R)-3-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-2-fluoro-3-hydroxy-2-methylpropanoyl)-4-benzyloxazolidin-2-one
1616508-45-2

(S)-3-((2R,3R)-3-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-2-fluoro-3-hydroxy-2-methylpropanoyl)-4-benzyloxazolidin-2-one

(3R,4R,5R)-3‑fluoro‑4‑hydroxy‑5‑(hydroxymethyl)‑3‑methyltetrahydrofuran‑2‑one
879551-04-9

(3R,4R,5R)-3‑fluoro‑4‑hydroxy‑5‑(hydroxymethyl)‑3‑methyltetrahydrofuran‑2‑one

Conditions
ConditionsYield
With lithium hydroxide monohydrate; dihydrogen peroxide In tetrahydrofuran; water at 0 - 5℃; for 1h;70%
(S)-3-((2R,3R)-3-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-2-fluoro-3-hydroxy-2-methylpropanoyl)-4-isopropyloxazolidin-2-one
1616508-57-6

(S)-3-((2R,3R)-3-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-2-fluoro-3-hydroxy-2-methylpropanoyl)-4-isopropyloxazolidin-2-one

(3R,4R,5R)-3‑fluoro‑4‑hydroxy‑5‑(hydroxymethyl)‑3‑methyltetrahydrofuran‑2‑one
879551-04-9

(3R,4R,5R)-3‑fluoro‑4‑hydroxy‑5‑(hydroxymethyl)‑3‑methyltetrahydrofuran‑2‑one

Conditions
ConditionsYield
With lithium hydroxide monohydrate; dihydrogen peroxide In tetrahydrofuran; water at 0 - 5℃; for 1h;67%
((2S,3R,4R)-4-fluoro-3-hydroxy-4-methyl-5-oxotetrahydrofuran-2-yl)methyl methanesulfonate

((2S,3R,4R)-4-fluoro-3-hydroxy-4-methyl-5-oxotetrahydrofuran-2-yl)methyl methanesulfonate

(3R,4R,5R)-3‑fluoro‑4‑hydroxy‑5‑(hydroxymethyl)‑3‑methyltetrahydrofuran‑2‑one
879551-04-9

(3R,4R,5R)-3‑fluoro‑4‑hydroxy‑5‑(hydroxymethyl)‑3‑methyltetrahydrofuran‑2‑one

Conditions
ConditionsYield
With water; potassium hydroxide In ethanol for 4h; Reflux;45%
C6H15N*C11H19FO8S

C6H15N*C11H19FO8S

(3R,4R,5R)-3‑fluoro‑4‑hydroxy‑5‑(hydroxymethyl)‑3‑methyltetrahydrofuran‑2‑one
879551-04-9

(3R,4R,5R)-3‑fluoro‑4‑hydroxy‑5‑(hydroxymethyl)‑3‑methyltetrahydrofuran‑2‑one

Conditions
ConditionsYield
Stage #1: C6H15N*C11H19FO8S With hydrogenchloride; water at 90℃; for 0.5h;
Stage #2: With barium(II) chloride In water at 90℃; for 4h;
Stage #1: C6H15N*C11H19FO8S With hydrogenchloride at 90 - 92℃; for 0.5h;
Stage #2: With barium(II) chloride In water for 4h; Temperature;
C13H22FNO4

C13H22FNO4

A

(3R,4R,5R)-3‑fluoro‑4‑hydroxy‑5‑(hydroxymethyl)‑3‑methyltetrahydrofuran‑2‑one
879551-04-9

(3R,4R,5R)-3‑fluoro‑4‑hydroxy‑5‑(hydroxymethyl)‑3‑methyltetrahydrofuran‑2‑one

B

(3S,4R,5R)-3-fluoro-4-hydroxy-5-(hydroxymethyl)-3-methyldihydrofuran-2(3H)-one
1040882-61-8

(3S,4R,5R)-3-fluoro-4-hydroxy-5-(hydroxymethyl)-3-methyldihydrofuran-2(3H)-one

Conditions
ConditionsYield
With water; acetic acid at 95℃; for 2 - 5h; Product distribution / selectivity;
C15H19FO4S

C15H19FO4S

A

(3R,4R,5R)-3‑fluoro‑4‑hydroxy‑5‑(hydroxymethyl)‑3‑methyltetrahydrofuran‑2‑one
879551-04-9

(3R,4R,5R)-3‑fluoro‑4‑hydroxy‑5‑(hydroxymethyl)‑3‑methyltetrahydrofuran‑2‑one

B

(3S,4R,5R)-3-fluoro-4-hydroxy-5-(hydroxymethyl)-3-methyldihydrofuran-2(3H)-one
1040882-61-8

(3S,4R,5R)-3-fluoro-4-hydroxy-5-(hydroxymethyl)-3-methyldihydrofuran-2(3H)-one

Conditions
ConditionsYield
With water; acetic acid at 95℃; for 2 - 5h; Product distribution / selectivity;
C16H18FNO6

C16H18FNO6

A

(3R,4R,5R)-3‑fluoro‑4‑hydroxy‑5‑(hydroxymethyl)‑3‑methyltetrahydrofuran‑2‑one
879551-04-9

(3R,4R,5R)-3‑fluoro‑4‑hydroxy‑5‑(hydroxymethyl)‑3‑methyltetrahydrofuran‑2‑one

B

(3S,4R,5R)-3-fluoro-4-hydroxy-5-(hydroxymethyl)-3-methyldihydrofuran-2(3H)-one
1040882-61-8

(3S,4R,5R)-3-fluoro-4-hydroxy-5-(hydroxymethyl)-3-methyldihydrofuran-2(3H)-one

Conditions
ConditionsYield
With water; acetic acid at 95℃; for 2 - 5h; Product distribution / selectivity;
C15H19FO4S

C15H19FO4S

A

(3R,4R,5R)-3‑fluoro‑4‑hydroxy‑5‑(hydroxymethyl)‑3‑methyltetrahydrofuran‑2‑one
879551-04-9

(3R,4R,5R)-3‑fluoro‑4‑hydroxy‑5‑(hydroxymethyl)‑3‑methyltetrahydrofuran‑2‑one

B

(3S,4R,5R)-3-fluoro-4-hydroxy-5-(hydroxymethyl)-3-methyldihydrofuran-2(3H)-one
1040882-61-8

(3S,4R,5R)-3-fluoro-4-hydroxy-5-(hydroxymethyl)-3-methyldihydrofuran-2(3H)-one

Conditions
ConditionsYield
With water; acetic acid at 90℃; for 2h; optical yield given as %de;
C16H18FNO6

C16H18FNO6

A

(3R,4R,5R)-3‑fluoro‑4‑hydroxy‑5‑(hydroxymethyl)‑3‑methyltetrahydrofuran‑2‑one
879551-04-9

(3R,4R,5R)-3‑fluoro‑4‑hydroxy‑5‑(hydroxymethyl)‑3‑methyltetrahydrofuran‑2‑one

B

(3S,4R,5R)-3-fluoro-4-hydroxy-5-(hydroxymethyl)-3-methyldihydrofuran-2(3H)-one
1040882-61-8

(3S,4R,5R)-3-fluoro-4-hydroxy-5-(hydroxymethyl)-3-methyldihydrofuran-2(3H)-one

Conditions
ConditionsYield
With water; acetic acid at 90℃; for 2h; optical yield given as %de;
C11H19FO5
1033394-83-0

C11H19FO5

(3R,4R,5R)-3‑fluoro‑4‑hydroxy‑5‑(hydroxymethyl)‑3‑methyltetrahydrofuran‑2‑one
879551-04-9

(3R,4R,5R)-3‑fluoro‑4‑hydroxy‑5‑(hydroxymethyl)‑3‑methyltetrahydrofuran‑2‑one

Conditions
ConditionsYield
With hydrogenchloride In ethanol; water at 20℃; for 15h;
With hydrogenchloride; water In ethanol at 20℃; for 21h;
(2S,3R)-3-[(4R)-2,2-dimethyl-[1,3]dioxolane-4-yl]-2,3-dihydroxy-2-methylpropionic acid ethyl ester
93635-76-8

(2S,3R)-3-[(4R)-2,2-dimethyl-[1,3]dioxolane-4-yl]-2,3-dihydroxy-2-methylpropionic acid ethyl ester

(3R,4R,5R)-3‑fluoro‑4‑hydroxy‑5‑(hydroxymethyl)‑3‑methyltetrahydrofuran‑2‑one
879551-04-9

(3R,4R,5R)-3‑fluoro‑4‑hydroxy‑5‑(hydroxymethyl)‑3‑methyltetrahydrofuran‑2‑one

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: fluorosulfonyl fluoride; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine tris(hydrogen fluoride) / acetonitrile / 5 h / -15 - 90 °C
2: 2,2-dimethoxy-propane; hydrogenchloride; water / tetrahydrofuran / 3 h / 20 °C
3: hydrogenchloride; water / ethanol / 21 h / 20 °C
View Scheme
Multi-step reaction with 3 steps
1.1: triethylamine; sulfuryl dichloride / dichloromethane / 2 h / 0 - 20 °C
2.1: tetraethylammonium fluoride / 1,4-dioxane / 16 h / 120 °C
2.2: 3 h / 20 °C
3.1: water; hydrogenchloride / ethanol / 48 h / 20 °C
View Scheme
Multi-step reaction with 3 steps
1.1: Isopropyl acetate; triethylamine; thionyl chloride / acetonitrile / 1 h / 6 - 9 °C
1.2: 0.5 h
2.1: triethylamine tris(hydrogen fluoride) / 2 h / 82 - 85 °C
3.1: hydrogenchloride / 0.5 h / 90 - 92 °C
3.2: 4 h
View Scheme
C10H18O6
1351925-17-1

C10H18O6

(3R,4R,5R)-3‑fluoro‑4‑hydroxy‑5‑(hydroxymethyl)‑3‑methyltetrahydrofuran‑2‑one
879551-04-9

(3R,4R,5R)-3‑fluoro‑4‑hydroxy‑5‑(hydroxymethyl)‑3‑methyltetrahydrofuran‑2‑one

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: fluorosulfonyl fluoride; triethylamine; 1,8-diazabicyclo[5.4.0]undec-7-ene hydrofluoride / acetonitrile / 5 h / 0 - 55 °C
2: 2,2-dimethoxy-propane; water; sulfuric acid / 1,4-dioxane / 16 h / 20 °C / pH 2 - 3 / Cooling with ice
3: hydrogenchloride; water / ethanol / 18 h / 20 °C
View Scheme
C10H16FO8S(1-)

C10H16FO8S(1-)

(3R,4R,5R)-3‑fluoro‑4‑hydroxy‑5‑(hydroxymethyl)‑3‑methyltetrahydrofuran‑2‑one
879551-04-9

(3R,4R,5R)-3‑fluoro‑4‑hydroxy‑5‑(hydroxymethyl)‑3‑methyltetrahydrofuran‑2‑one

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 2,2-dimethoxy-propane; water; sulfuric acid / 1,4-dioxane / 16 h / 20 °C / pH 2 - 3 / Cooling with ice
2: hydrogenchloride; water / ethanol / 18 h / 20 °C
View Scheme
C10H17FO5

C10H17FO5

(3R,4R,5R)-3‑fluoro‑4‑hydroxy‑5‑(hydroxymethyl)‑3‑methyltetrahydrofuran‑2‑one
879551-04-9

(3R,4R,5R)-3‑fluoro‑4‑hydroxy‑5‑(hydroxymethyl)‑3‑methyltetrahydrofuran‑2‑one

Conditions
ConditionsYield
With hydrogenchloride; water In ethanol at 20℃; for 18h; Solvent;
C11H18O4
130606-67-6

C11H18O4

(3R,4R,5R)-3‑fluoro‑4‑hydroxy‑5‑(hydroxymethyl)‑3‑methyltetrahydrofuran‑2‑one
879551-04-9

(3R,4R,5R)-3‑fluoro‑4‑hydroxy‑5‑(hydroxymethyl)‑3‑methyltetrahydrofuran‑2‑one

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: potassium permanganate / acetone / 5 h / 0 - 5 °C
2.1: triethylamine; sulfuryl dichloride / dichloromethane / 2 h / 0 - 20 °C
3.1: tetraethylammonium fluoride / 1,4-dioxane / 16 h / 120 °C
3.2: 3 h / 20 °C
4.1: water; hydrogenchloride / ethanol / 48 h / 20 °C
View Scheme
Multi-step reaction with 4 steps
1.1: sodium hydrogencarbonate; sodium permanganate; ethylene glycol / acetone / 1.5 h / -15 - 10 °C
2.1: Isopropyl acetate; triethylamine; thionyl chloride / acetonitrile / 1 h / 6 - 9 °C
2.2: 0.5 h
3.1: triethylamine tris(hydrogen fluoride) / 2 h / 82 - 85 °C
4.1: hydrogenchloride / 0.5 h / 90 - 92 °C
4.2: 4 h
View Scheme
C12H21FO4

C12H21FO4

(3R,4R,5R)-3‑fluoro‑4‑hydroxy‑5‑(hydroxymethyl)‑3‑methyltetrahydrofuran‑2‑one
879551-04-9

(3R,4R,5R)-3‑fluoro‑4‑hydroxy‑5‑(hydroxymethyl)‑3‑methyltetrahydrofuran‑2‑one

Conditions
ConditionsYield
With hydrogenchloride; water In ethanol at 20℃; for 48h;110 g
ethyl 2-fluoropropionate
349-43-9

ethyl 2-fluoropropionate

2,3-isopropylidene-glyceraldehyde
15186-48-8

2,3-isopropylidene-glyceraldehyde

A

(3R,4R,5R)-3‑fluoro‑4‑hydroxy‑5‑(hydroxymethyl)‑3‑methyltetrahydrofuran‑2‑one
879551-04-9

(3R,4R,5R)-3‑fluoro‑4‑hydroxy‑5‑(hydroxymethyl)‑3‑methyltetrahydrofuran‑2‑one

B

(3S,4R,5R)-3-fluoro-4-hydroxy-5-(hydroxymethyl)-3-methyldihydrofuran-2(3H)-one
1040882-61-8

(3S,4R,5R)-3-fluoro-4-hydroxy-5-(hydroxymethyl)-3-methyldihydrofuran-2(3H)-one

Conditions
ConditionsYield
Stage #1: ethyl 2-fluoropropionate; 2,3-isopropylidene-glyceraldehyde With lithium diisopropyl amide In tetrahydrofuran at -70 - 20℃; for 2h;
Stage #2: With acetic acid In water at 90℃; for 2h;
...Expand
C18H22FNO6

C18H22FNO6

(3R,4R,5R)-3‑fluoro‑4‑hydroxy‑5‑(hydroxymethyl)‑3‑methyltetrahydrofuran‑2‑one
879551-04-9

(3R,4R,5R)-3‑fluoro‑4‑hydroxy‑5‑(hydroxymethyl)‑3‑methyltetrahydrofuran‑2‑one

Conditions
ConditionsYield
With hydrogenchloride In ethanol; water for 4h; Reflux;
(S,E)-3-(2,2-dimethyl-1,3-dioxolan-4-yl)-2-methylpropionic acid ethyl ester
81997-76-4

(S,E)-3-(2,2-dimethyl-1,3-dioxolan-4-yl)-2-methylpropionic acid ethyl ester

(3R,4R,5R)-3‑fluoro‑4‑hydroxy‑5‑(hydroxymethyl)‑3‑methyltetrahydrofuran‑2‑one
879551-04-9

(3R,4R,5R)-3‑fluoro‑4‑hydroxy‑5‑(hydroxymethyl)‑3‑methyltetrahydrofuran‑2‑one

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: potassium carbonate; dihydrogen peroxide / ethanol; benzonitrile / 0 °C
2: triethylamine; triethylamine tris(hydrogen fluoride) / 80 °C / Inert atmosphere
3: hydrogenchloride / ethanol; water / 24 h / 50 °C
View Scheme
C11H18O5

C11H18O5

(3R,4R,5R)-3‑fluoro‑4‑hydroxy‑5‑(hydroxymethyl)‑3‑methyltetrahydrofuran‑2‑one
879551-04-9

(3R,4R,5R)-3‑fluoro‑4‑hydroxy‑5‑(hydroxymethyl)‑3‑methyltetrahydrofuran‑2‑one

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: triethylamine; triethylamine tris(hydrogen fluoride) / 80 °C / Inert atmosphere
2: hydrogenchloride / ethanol; water / 24 h / 50 °C
View Scheme
C10H17FO5

C10H17FO5

A

(3R,4R,5R)-3‑fluoro‑4‑hydroxy‑5‑(hydroxymethyl)‑3‑methyltetrahydrofuran‑2‑one
879551-04-9

(3R,4R,5R)-3‑fluoro‑4‑hydroxy‑5‑(hydroxymethyl)‑3‑methyltetrahydrofuran‑2‑one

B

(3S,4R,5R)-3-fluoro-4-hydroxy-5-(hydroxymethyl)-3-methyldihydrofuran-2(3H)-one
1040882-61-8

(3S,4R,5R)-3-fluoro-4-hydroxy-5-(hydroxymethyl)-3-methyldihydrofuran-2(3H)-one

C

C6H9FO4

C6H9FO4

D

C6H9FO4

C6H9FO4

Conditions
ConditionsYield
With acetic acid In water at 90℃; for 1h; Overall yield = 28.9 g;
...Expand
C14H24FNO4

C14H24FNO4

A

(3R,4R,5R)-3‑fluoro‑4‑hydroxy‑5‑(hydroxymethyl)‑3‑methyltetrahydrofuran‑2‑one
879551-04-9

(3R,4R,5R)-3‑fluoro‑4‑hydroxy‑5‑(hydroxymethyl)‑3‑methyltetrahydrofuran‑2‑one

B

(3S,4R,5R)-3-fluoro-4-hydroxy-5-(hydroxymethyl)-3-methyldihydrofuran-2(3H)-one
1040882-61-8

(3S,4R,5R)-3-fluoro-4-hydroxy-5-(hydroxymethyl)-3-methyldihydrofuran-2(3H)-one

C

C6H9FO4

C6H9FO4

D

C6H9FO4

C6H9FO4

Conditions
ConditionsYield
With acetic acid In water at 90℃; for 1h; Overall yield = 8.72 g;
...Expand
ethyl (E)-3-(2,2-dimethyl-1,3-dioxolan-4-yl)-2-methyl-2-propenoate
127642-52-8

ethyl (E)-3-(2,2-dimethyl-1,3-dioxolan-4-yl)-2-methyl-2-propenoate

(3R,4R,5R)-3‑fluoro‑4‑hydroxy‑5‑(hydroxymethyl)‑3‑methyltetrahydrofuran‑2‑one
879551-04-9

(3R,4R,5R)-3‑fluoro‑4‑hydroxy‑5‑(hydroxymethyl)‑3‑methyltetrahydrofuran‑2‑one

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: sodium permanganate; ethylene glycol; sodium hydrogencarbonate / water; ethyl acetate / -10 - 0 °C / Large scale
2: triethylamine; sulfuryl dichloride / ethyl acetate / 5 - 25 °C / Large scale
3: potassium fluoride / ethyl acetate / 5 h / Reflux; Large scale
4: hydrogenchloride / water; ethyl acetate / 2 h / 85 - 90 °C / Large scale
View Scheme
C11H20O6

C11H20O6

(3R,4R,5R)-3‑fluoro‑4‑hydroxy‑5‑(hydroxymethyl)‑3‑methyltetrahydrofuran‑2‑one
879551-04-9

(3R,4R,5R)-3‑fluoro‑4‑hydroxy‑5‑(hydroxymethyl)‑3‑methyltetrahydrofuran‑2‑one

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: triethylamine; sulfuryl dichloride / ethyl acetate / 5 - 25 °C / Large scale
2: potassium fluoride / ethyl acetate / 5 h / Reflux; Large scale
3: hydrogenchloride / water; ethyl acetate / 2 h / 85 - 90 °C / Large scale
View Scheme
(3R,4R,5R)-3‑fluoro‑4‑hydroxy‑5‑(hydroxymethyl)‑3‑methyltetrahydrofuran‑2‑one
879551-04-9

(3R,4R,5R)-3‑fluoro‑4‑hydroxy‑5‑(hydroxymethyl)‑3‑methyltetrahydrofuran‑2‑one

(3R,4R,5R)-3-fluoro-5-(hydroxymethyl)-3-methyltetrahydrofuran-2,4-diol

(3R,4R,5R)-3-fluoro-5-(hydroxymethyl)-3-methyltetrahydrofuran-2,4-diol

Conditions
ConditionsYield
With lithium borohydride In tetrahydrofuran at 0℃; for 6h; Solvent; Concentration; Inert atmosphere;94%
With lithium tri-t-butoxyaluminum hydride In tetrahydrofuran at -20 - 0℃; for 0.5h; Reagent/catalyst;
(3R,4R,5R)-3‑fluoro‑4‑hydroxy‑5‑(hydroxymethyl)‑3‑methyltetrahydrofuran‑2‑one
879551-04-9

(3R,4R,5R)-3‑fluoro‑4‑hydroxy‑5‑(hydroxymethyl)‑3‑methyltetrahydrofuran‑2‑one

tert-butyldimethylsilyl chloride
18162-48-6

tert-butyldimethylsilyl chloride

C12H23FO4Si

C12H23FO4Si

Conditions
ConditionsYield
With pyridine; 1H-imidazole at 0 - 20℃; for 16h;88%
With pyridine; 1H-imidazole In dichloromethane at 20℃; Cooling with ice;63%
With pyridine; 1H-imidazole In dichloromethane at 20℃; Cooling with ice;57.3%
(3R,4R,5R)-3‑fluoro‑4‑hydroxy‑5‑(hydroxymethyl)‑3‑methyltetrahydrofuran‑2‑one
879551-04-9

(3R,4R,5R)-3‑fluoro‑4‑hydroxy‑5‑(hydroxymethyl)‑3‑methyltetrahydrofuran‑2‑one

benzoyl chloride
98-88-4

benzoyl chloride

((2R,3R,4R)-3-benzoyloxy-4-fluoro-4-methyl-5-oxo-tetrahydrofuran-2-yl)methyl benzoate
874638-80-9

((2R,3R,4R)-3-benzoyloxy-4-fluoro-4-methyl-5-oxo-tetrahydrofuran-2-yl)methyl benzoate

Conditions
ConditionsYield
With pyridine at 20℃; for 0.333333h;87%
With dmap; triethylamine In dichloromethane at 0 - 20℃; for 12h;86%
With dmap; triethylamine In acetonitrile at 5 - 20℃; for 2h; Temperature;84.2%
(3R,4R,5R)-3‑fluoro‑4‑hydroxy‑5‑(hydroxymethyl)‑3‑methyltetrahydrofuran‑2‑one
879551-04-9

(3R,4R,5R)-3‑fluoro‑4‑hydroxy‑5‑(hydroxymethyl)‑3‑methyltetrahydrofuran‑2‑one

((2R,3R,4R)-3-(benzoyloxy)-4-fluoro-5-hydroxy-4-methyltetrahydrofuran-2-yl)methyl benzoate

((2R,3R,4R)-3-(benzoyloxy)-4-fluoro-5-hydroxy-4-methyltetrahydrofuran-2-yl)methyl benzoate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: pyridine / 0.75 h / 0 - 20 °C
2: lithium tri-t-butoxyaluminum hydride / tetrahydrofuran / 1 h / -78 - -20 °C / Inert atmosphere
View Scheme
(3R,4R,5R)-3‑fluoro‑4‑hydroxy‑5‑(hydroxymethyl)‑3‑methyltetrahydrofuran‑2‑one
879551-04-9

(3R,4R,5R)-3‑fluoro‑4‑hydroxy‑5‑(hydroxymethyl)‑3‑methyltetrahydrofuran‑2‑one

(((2R,3R,4R,5R)-3-(benzoyloxy)-5-bromo-4-fluoro-4-methyltetrahydrofuran-2-yl)methyl benzoate)
1199809-24-9

(((2R,3R,4R,5R)-3-(benzoyloxy)-5-bromo-4-fluoro-4-methyltetrahydrofuran-2-yl)methyl benzoate)

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: pyridine / 0.75 h / 0 - 20 °C
2: lithium tri-t-butoxyaluminum hydride / tetrahydrofuran / 1 h / -78 - -20 °C / Inert atmosphere
3: carbon tetrabromide; triphenylphosphine / dichloromethane / 0.33 h / -25 - -20 °C / Inert atmosphere
View Scheme
(3R,4R,5R)-3‑fluoro‑4‑hydroxy‑5‑(hydroxymethyl)‑3‑methyltetrahydrofuran‑2‑one
879551-04-9

(3R,4R,5R)-3‑fluoro‑4‑hydroxy‑5‑(hydroxymethyl)‑3‑methyltetrahydrofuran‑2‑one

(2R,3R,4R,5R)-5-(2-amino-6-chloro-9H-purin-9-yl)-2-((benzoyloxy)methyl)-4-fluoro-4-methyltetrahydrofuran-3-yl benzoate
1199809-26-1

(2R,3R,4R,5R)-5-(2-amino-6-chloro-9H-purin-9-yl)-2-((benzoyloxy)methyl)-4-fluoro-4-methyltetrahydrofuran-3-yl benzoate

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: pyridine / 0.75 h / 0 - 20 °C
2.1: lithium tri-t-butoxyaluminum hydride / tetrahydrofuran / 1 h / -78 - -20 °C / Inert atmosphere
3.1: carbon tetrabromide; triphenylphosphine / dichloromethane / 0.33 h / -25 - -20 °C / Inert atmosphere
4.1: potassium tert-butylate / acetonitrile; tert-butyl alcohol / 0.5 h / 35 °C
4.2: 50 °C
View Scheme
(3R,4R,5R)-3‑fluoro‑4‑hydroxy‑5‑(hydroxymethyl)‑3‑methyltetrahydrofuran‑2‑one
879551-04-9

(3R,4R,5R)-3‑fluoro‑4‑hydroxy‑5‑(hydroxymethyl)‑3‑methyltetrahydrofuran‑2‑one

C31H30FN5O5
1613589-61-9

C31H30FN5O5

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: pyridine / 0.75 h / 0 - 20 °C
2.1: lithium tri-t-butoxyaluminum hydride / tetrahydrofuran / 1 h / -78 - -20 °C / Inert atmosphere
3.1: carbon tetrabromide; triphenylphosphine / dichloromethane / 0.33 h / -25 - -20 °C / Inert atmosphere
4.1: potassium tert-butylate / acetonitrile; tert-butyl alcohol / 0.5 h / 35 °C
4.2: 50 °C
5.1: silver nitrate / dichloromethane / 20 °C
5.2: 12 h / 20 °C
View Scheme
(3R,4R,5R)-3‑fluoro‑4‑hydroxy‑5‑(hydroxymethyl)‑3‑methyltetrahydrofuran‑2‑one
879551-04-9

(3R,4R,5R)-3‑fluoro‑4‑hydroxy‑5‑(hydroxymethyl)‑3‑methyltetrahydrofuran‑2‑one

C31H29FIN5O4
1613589-62-0

C31H29FIN5O4

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: pyridine / 0.75 h / 0 - 20 °C
2.1: lithium tri-t-butoxyaluminum hydride / tetrahydrofuran / 1 h / -78 - -20 °C / Inert atmosphere
3.1: carbon tetrabromide; triphenylphosphine / dichloromethane / 0.33 h / -25 - -20 °C / Inert atmosphere
4.1: potassium tert-butylate / acetonitrile; tert-butyl alcohol / 0.5 h / 35 °C
4.2: 50 °C
5.1: silver nitrate / dichloromethane / 20 °C
5.2: 12 h / 20 °C
6.1: triphenylphosphine; pyridine; iodine / 20 °C
View Scheme

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