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879551-04-9

Basic Information
CAS No.: 879551-04-9
Name: (3R,4R,5R)-3-fluoro-4-hydroxy-5-(hydroxyMethyl)-3-Methyl-dihydrofuran-2(3H)-one
Article Data: 20
Molecular Structure:
Molecular Structure of 879551-04-9 ((3R,4R,5R)-3-fluoro-4-hydroxy-5-(hydroxyMethyl)-3-Methyl-dihydrofuran-2(3H)-one)
Formula: C6H9FO4
Molecular Weight: 164.133
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
Density: 1.42±0.1 g/cm3 (20 oC 760 Torr), Calc.*
Melting Point: 142-143 oC (ethyl acetate heptane )**
Boiling Point: 352.7±42.0 °C(Predicted)
Solubility: Very soluble (1000 g/L) (25 oC), Calc.*
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

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

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%
874638-80-9

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

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;
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

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

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

A

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

Conditions
ConditionsYield
With trifluoroacetic acid In 1,4-dioxane; water at 20℃; for 48h;A 83%
B 6%
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

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%
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

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

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

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;
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  • 879551-04-9

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