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(3R,4R,5R)-3-fluoro-4-hydroxy-5-(hydroxyMethyl)-3-Methyl-dihydrofuran-2(3H)-one is a complex organic compound with a unique molecular structure, featuring a fluorinated dihydrofuran ring and multiple chiral centers. Its stereochemistry is defined by the (3R,4R,5R) configuration, which is crucial for its potential applications in asymmetric synthesis.

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  • 879551-04-9 Structure
  • Basic information

    1. Product Name: (3R,4R,5R)-3-fluoro-4-hydroxy-5-(hydroxyMethyl)-3-Methyl-dihydrofuran-2(3H)-one
    2. 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;(3R,4R,5R)-3-Fluoro-4-hydroxy-5-(hydroxymethyl)-3-methyl-tetrahydrofuran-2-one;D-erythro-Pentonic acid, 2-deoxy-2-fluoro-2-methyl-, |-lactone;D-erythro-Pentonic acid, 2-deoxy-2-fluoro-2-methyl-, gamma-lactone;-3-Fluoro-4-hydroxy-5-(hydroxymethyl);-3-methyldihydrofuran-2(3H)
    3. CAS NO:879551-04-9
    4. Molecular Formula: C6H9FO4
    5. Molecular Weight: 164.1316632
    6. EINECS: N/A
    7. Product Categories: Sofosbuvir intermediate
    8. Mol File: 879551-04-9.mol
  • Chemical Properties

    1. Melting Point: 142-143℃ (ethyl acetate heptane )
    2. Boiling Point: 352.7±42.0 °C(Predicted)
    3. Flash Point: N/A
    4. Appearance: /
    5. Density: 1.42±0.1 g/cm3 (20 oC 760 Torr), Calc.*
    6. Refractive Index: N/A
    7. Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
    8. Solubility: N/A
    9. PKA: 11.46±0.60(Predicted)
    10. CAS DataBase Reference: (3R,4R,5R)-3-fluoro-4-hydroxy-5-(hydroxyMethyl)-3-Methyl-dihydrofuran-2(3H)-one(CAS DataBase Reference)
    11. NIST Chemistry Reference: (3R,4R,5R)-3-fluoro-4-hydroxy-5-(hydroxyMethyl)-3-Methyl-dihydrofuran-2(3H)-one(879551-04-9)
    12. EPA Substance Registry System: (3R,4R,5R)-3-fluoro-4-hydroxy-5-(hydroxyMethyl)-3-Methyl-dihydrofuran-2(3H)-one(879551-04-9)
  • Safety Data

    1. Hazard Codes: N/A
    2. Statements: N/A
    3. Safety Statements: N/A
    4. WGK Germany:
    5. RTECS:
    6. HazardClass: N/A
    7. PackingGroup: N/A
    8. Hazardous Substances Data: 879551-04-9(Hazardous Substances Data)

879551-04-9 Usage

Uses

Used in Pharmaceutical Industry:
(3R,4R,5R)-3-fluoro-4-hydroxy-5-(hydroxyMethyl)-3-Methyl-dihydrofuran-2(3H)-one is used as a key intermediate in the asymmetric synthesis of complex organic molecules, particularly for the preparation of dibenzoyl fluoro methyl-D-ribono-γ-lactone. (3R,4R,5R)-3-fluoro-4-hydroxy-5-(hydroxyMethyl)-3-Methyl-dihydrofuran-2(3H)-one is synthesized via asymmetric aldol condensation and enzymic hydrolysis from isopropylidene-D-glyceraldehyde and Et fluoropropionate, showcasing its importance in the development of novel pharmaceutical agents and advanced drug delivery systems.

Check Digit Verification of cas no

The CAS Registry Mumber 879551-04-9 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 8,7,9,5,5 and 1 respectively; the second part has 2 digits, 0 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 879551-04:
(8*8)+(7*7)+(6*9)+(5*5)+(4*5)+(3*1)+(2*0)+(1*4)=219
219 % 10 = 9
So 879551-04-9 is a valid CAS Registry Number.

879551-04-9SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 19, 2017

Revision Date: Aug 19, 2017

1.Identification

1.1 GHS Product identifier

Product name (3R,4R,5R)-3-fluoro-4-hydroxy-5-(hydroxymethyl)-3-methyloxolan-2-one

1.2 Other means of identification

Product number -
Other names FRAGMENTA ERY012

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:879551-04-9 SDS

879551-04-9Synthetic 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;
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;
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;
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

879551-04-9Relevant articles and documents

BI- AND MONOCYCLIC NUCLEOSIDE ANALOGS FOR TREATMENT OF HEPATITIS E

-

, (2021/10/22)

The present disclosure is directed toward bi- and monocyclic nucleoside analogs, and compositions comprising these compounds for use in the treatment of hepatitis E infections.

Method for preparing 3-fluoro-4-hydroxy-5-(hydroxymethyl)-3-methyltetrahydrofuran-2-one

-

Paragraph 0020-0044, (2020/11/05)

The invention discloses a method for preparing 3-fluoro-4-hydroxy-5-(hydroxymethyl)-3-methyltetrahydrofuran-2-one, comprising the following steps that: ((2R, 3R, 4R)-3-(benzyloxy)-4-fluoro-4-methyl-5-oxotetrahydrofuran-2-yl) methyl benzoate is dispersed in an organic solvent, excessive strong acid is added for heating reflux, the organic solvent is removed, and pulping, filtering and drying are performed, wherein the strong acid is methanesulfonic acid, sulfuric acid, trifluoromethanesulfonic acid or concentrated hydrochloric acid. ((2R, 3R, 4R)-3-(benzyloxy)-4-fluoro-4-methyl-5-oxotetrahydrofuran-2-yl) methyl benzoate is adopted as a raw material to be subjected to a reflux reaction with excessive specific strong acid, a high-purity and high-yield product can be obtained only through a one-step reaction, the process steps are simple, and mass production of the product is facilitated.

PROCESS FOR PREPARATION OF LACTONE DERIVATIVES AND INTERMEDIATES THEREOF

-

Page/Page column 36; 37, (2018/03/09)

A novel process for the preparation of lactone derivatives, and intermediates thereof is described. The lactone derivatives are important precursors for the synthesis of anti-hepatitis C virus agents, including sofosbuvir.

Preparation method of sofosbuvir intermediate

-

Paragraph 0108; 0109; 0112; 0113; 0116; 0117, (2018/03/01)

The invention discloses a preparation method of a sofosbuvir intermediate of (2R)-2-deoxy-2-fluoro-2-methyl-D-erythro-pentonic acid-g-lactone 3,5-dibenzoate. The intermediate structure corresponds toa formula I shown as the description. The method comprises the step that the sofosbuvir intermediate shown as the formula I is finally obtained by using (D2) (S)-(+)-4-phenyl-2-oxazolidinone of a compound shown as a formula II as a raw material through six-step reaction of condensation, fluorination, Adol addition, oxidation cyclization, isomerization and benzoylation. The preparation method hasthe advantages that the raw materials are cheap and can be easily obtained; the reaction conditions are mild; the route is short; the yield is high; three wastes are few; the pollution is little; thepreparation method is suitable for industrial production.

Synthesizing method for drug intermediate

-

Paragraph 0103-0106; 0111-0113; 0117-0119, (2017/06/02)

The invention discloses a synthesizing method for a drug intermediate, and relates to the field of drug synthesis, in particular to the field of organic synthesis. In the synthesizing method, compound V(4S,5R)-ethyl-5-((R)-2,2-dimethyl-1,3-dioxolame-4-base)-4-methyl-1,3,2-dioxathiolane-4- carboxylic acid-2,2'dioxide serves as a raw material, a compound II is prepared through three synthesizing methods, and an intermediate compound I is prepared through the compound II. The provided synthesizing technology has the beneficial effects that cost is low, few byproducts are generated, the yield is high, and pollution to the environment is weak.

Preparation for sofosbuvir key intermediate

-

Paragraph 0017; 0018, (2016/10/20)

The invention relates to preparation for a sofosbuvir key intermediate. With (E)-(S)-3-(2,2-dimethyl-1,3-dioxolane-4-base)-2-ethyl methacrylate being an initial raw material, preparation of 3,5-bis-O-benzoyl-2-deoxidation-2-fluorine-2-C-methyl-D-riboic acid-gamma-lactone is achieved through an epoxidation reaction, fluoridation, a de-acetonylidene cyclization reaction and a benzoyl reaction. According to the method, a synthesis route is short, and in the reaction process, a reagent that oxidability is high, and in the aftertreatment process, potassium permanganate or sodium permanganate and high-corrosivity SOCl2 deep in waste water color will generate a lot of waste water will not be involved.

Preparation method for 3,5-dibenzoyl-2-deoxy-2-fluoro-2-methyl-D-ribono-gamma-lactone

-

Paragraph 0030; 0054, (2017/06/02)

The invention discloses a preparation method for 3,5-dibenzoyl-2-deoxy-2-fluoro-2-methyl-D-ribono-gamma-lactone. The preparation method comprises the following steps: subjecting a starting raw material D-mannitol to acetone protection and sodium periodate oxidation; then subjecting the treated D-mannitol and a self-made ylide reagent to the Witting reaction; then carrying out selective oxidation by using an aqueous sodium permanganate solution; then successively carrying out sulfonylation, fluorination with potassium fluoride, and ring closing with a concentrated protective group protective group; protecting the hydroxyl group by using benzoyl chloride; and then carrying out purification so as to obtain the final product 3,5-dibenzoyl-2-deoxy-2-fluoro-2-methyl-D-ribono-gamma-lactone. The preparation method provided by the invention uses easily available and cheap raw materials, so production cost is greatly reduced; and the operation of the preparation method is coherent and simple, and the quantity of waste gas, waste water and industrial residues is lower than the quantity of waste gas, waste water and industrial residues reported in the prior art.

Method for preparing intermediate of Sofosbuvir

-

, (2016/12/26)

The invention provides a method for preparing 3,5-bis-O-benzoyl-2-deoxy-2-fluoro-2-C-methyl-D-ribose-gamma-lactone of D-ribofuranose lactone (structural formula 1). The compound is an important intermediate of a hepatitis C virus (HCV) NS5B polymerase inhibitor Sofosbuvir. The formula 1 is shown in the specification.

PRODUCTION METHOD OF (2R)-2-FLUORO-2-C-METHYL-D-RIBONO-γ-LACTONE

-

Paragraph 0116; 0117; 0118, (2016/11/07)

PROBLEM TO BE SOLVED: To provide a production method of (2R)-2-fluoro-2-C-methyl-D-ribono-γ-lactone. SOLUTION: A (2R)-2-fluoro-2-C-methyl-D-ribono-γ-lactone precursor containing various diastereomers can be produced by performing Reformatsky reaction using activated metal to a 2-fluoro-2-halopropionate derivative and a D-glyceraldehyde derivative. The obtained mixture containing the (2R)-2-fluoro-2-C-methyl-D-ribono-γ-lactone precursor is subjected to deprotection and lactonizing under an acidic condition, is converted to a diastereomer mixture containing 2-fluoro-2-C-methyl-D-ribono-γ-lactone and is recrystallized, thereby inducing the mixture to (2R)-2-fluoro-2-C-methyl-D-ribono-γ-lactone. COPYRIGHT: (C)2015,JPOandINPIT

(2R)-2-DEOXY-2,2-DISUBSTITUTED-RIBONO-1,4-LACTONE AND PREPARATION METHOD AND USE THEREOF

-

Paragraph 0064; 0065; 0066, (2015/11/02)

This invention disclose (2R)-2-deoxy-2,2-disubstituted-ribono-1,4-lactone in a single configuration and preparation method and use thereof. The (2R)-2-deoxy-2,2-disubstituted-ribono-1,4-lactone, or a pharmaceutically acceptable salt, an ester, a prodrug or a solvate thereof according to the invention are important intermediates of a variety of anti-viral and anti-tumor active ingredients. A compound obtained from (2R)-2-deoxy-2,2-disubstituted-ribono-1,4-lactone via an acylation reaction can be directly used for preparing various anti-viral and anti-tumor drugs. The Chiral synthesis method and the spontaneous resolution method of the compound of (2R)-2-deoxy-2,2-disubstituted-ribono-1,4-lactone according to the invention have the following advantages: the reaction routes are short and simple with high yield and low cost, which are suitable for industrial application.

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