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((2R,3R,4R)-3-(Benzoyloxy)-4-fluoro-4-methyl-5-oxotetrahydrofuran-2-yl)methyl benzoate
Cas No: 874638-80-9
USD $ 3.0-3.0 / Kilogram 1 Kilogram 1-100 Metric Ton/Month Dayang Chem (Hangzhou) Co.,Ltd. Contact Supplier
(2R)-2-Deoxy-2-fluoro-2-methyl-D-erythropentonic acid gamma-lactone 3,5-dibenzoate
Cas No: 874638-80-9
No Data 10 Milligram Amadis Chemical Co., Ltd. Contact Supplier
((2R,3R,4R)-3-(benzoyloxy)-4-fluoro-4-methyl-5-oxotetrahydrofuran-2-yl)methyl benzoate
Cas No: 874638-80-9
USD $ 1500.0-2200.0 / Gram 100 Gram 100 Kilogram/Month ACHIEVER SYSTEAM BIOCHEM CO., LTD. Contact Supplier
Sofosbuvir intermediate 874638-80-9
Cas No: 874638-80-9
No Data 1 Metric Ton Metric Ton/Day Hangzhou Maytime Bio-Tech Co.,Ltd. Contact Supplier
High quality ((2R,3R,4R)-3-(benzoyloxy)-4-fluoro-4-methyl-5-oxotetrahydrofuran-2-yl)methyl benzoate supplier in China
Cas No: 874638-80-9
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2-Deoxy-2-fluoro-2-methyl-D-erythropentenoic acid-r-lactone,3,5-dibenzoate
Cas No: 874638-80-9
USD $ 1.0-2.0 / Metric Ton 1 Metric Ton 100 Metric Ton/Week Hebei yanxi chemical co.,LTD. Contact Supplier
High quality Sofosbuvir Intermediate Cas 874638-80-9 with best price
Cas No: 874638-80-9
USD $ 12.0-16.0 / Gram 10 Gram 200 Kilogram/Year Wuhan Fortuna Chemical Co.,Ltd Contact Supplier
[(2R,3R,4R)-3-(Benzoyloxy)-4-fluoro-4-methyl-5-oxotetrahydrofuran-2-yl]-methyl benzoate
Cas No: 874638-80-9
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High Quality 99% 874638-80-9 ((2R,3R,4R)-3-(benzoyloxy)-4-fluoro-4-methyl-5-oxotetrahydrofuran-2-yl)methyl benzoate Manufacturer
Cas No: 874638-80-9
USD $ 0.1-0.1 / Gram 1 Gram 100 Metric Ton/Year Xi'an Xszo Chem Co., Ltd. Contact Supplier
874638-80-9 ((2R,3R,4R)-3-(benzoyloxy)-4-fluoro-4-methyl-5-oxotetrahydrofuran-2-yl)methyl benzoate
Cas No: 874638-80-9
No Data 1 Kilogram 20 Metric Ton/Day Henan Allgreen Chemical Co.,Ltd Contact Supplier

874638-80-9 Usage

Uses

neuromuscular blocking agent

874638-80-9SDS

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

1.2 Other means of identification

Product number -
Other names [(2R,3R,4R)-3-benzoyloxy-4-fluoro-4-methyl-5-oxooxolan-2-yl]methyl benzoate

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:874638-80-9 SDS

874638-80-9Synthetic route

[(2R,3R,4S)-4-fluoro-2,5-dihydroxy-4-methylpentane-1,3-diyl] dibenzoate

[(2R,3R,4S)-4-fluoro-2,5-dihydroxy-4-methylpentane-1,3-diyl] dibenzoate

((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 pyridinium chlorochromate In dichloromethane at 20℃; for 12h; Reagent/catalyst; Solvent; Temperature; Molecular sieve;95%
With hydrogenchloride; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; trichloroisocyanuric acid In dichloromethane; water at 10 - 20℃; for 2.5h;
C11H19FO5
1033394-83-0

C11H19FO5

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
Stage #1: C11H19FO5 With hydrogenchloride In ethanol; water at 20℃; for 22h;
Stage #2: benzoyl chloride With pyridine In water; acetonitrile at 0 - 30℃; for 1.16667h; Temperature;
95%
(3R,4R,5R)-3-methyl-3-fluoro-4-benzoyloxy-5-hydroxymethylbutyrolactone

(3R,4R,5R)-3-methyl-3-fluoro-4-benzoyloxy-5-hydroxymethylbutyrolactone

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 In dichloromethane at 20℃;91%
With triethylamine In dichloromethane at 0 - 20℃; for 3h;87%
With triethylamine In dichloromethane at 0 - 20℃; for 3h;87%
3,5-dibenzoyl-2-deoxy-2-hydroxy-2-methyl-D-ribose-γ-lactone

3,5-dibenzoyl-2-deoxy-2-hydroxy-2-methyl-D-ribose-γ-lactone

((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 triethylamine tris(hydrogen fluoride); triethylamine In acetonitrile Cooling with ice;90%
With fluorosulfonyl fluoride; triethylamine tris(hydrogen fluoride); triethylamine In acetonitrile Cooling with ice;87%
Stage #1: 3,5-dibenzoyl-2-deoxy-2-hydroxy-2-methyl-D-ribose-γ-lactone With triethylamine tris(hydrogen fluoride); triethylamine In ethyl acetate at -17℃; for 1h;
Stage #2: With fluorosulfonyl fluoride In ethyl acetate under 750.075 - 3750.38 Torr; Reagent/catalyst; Solvent; Temperature; Cooling;
87.6%
Stage #1: 3,5-dibenzoyl-2-deoxy-2-hydroxy-2-methyl-D-ribose-γ-lactone With triethylamine tris(hydrogen fluoride); triethylamine In acetonitrile
Stage #2: With potassium chloride In acetonitrile at 0℃; for 2h;
83%
(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%
3,5-di-O-benzoyl-2-C-methyl-D-ribono-γ-lactone
729596-46-7

3,5-di-O-benzoyl-2-C-methyl-D-ribono-γ-lactone

((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
Stage #1: 3,5-di-O-benzoyl-2-C-methyl-D-ribono-γ-lactone With pyridine; trifluoromethylsulfonic anhydride In dichloromethane at -40 - 20℃; for 1h;
Stage #2: With fluorosulfonyl fluoride; triethylamine tris(hydrogen fluoride); triethylamine In acetonitrile Cooling with ice;
78%
Multi-step reaction with 3 steps
1.1: pyridine / dichloromethane / 0.08 h / -10 °C
1.2: 20 °C
2.1: dichloromethane; water; dimethyl sulfoxide / Cooling with ice
3.1: triethylamine; triethylamine tris(hydrogen fluoride); fluorosulfonyl fluoride / acetonitrile / Cooling with ice
View Scheme
Multi-step reaction with 4 steps
1.1: pyridine / dichloromethane / 0.08 h / -10 °C
1.2: 20 °C
2.1: water / 0.42 h
3.1: triethylamine / water; acetone / 45 °C
4.1: triethylamine; triethylamine tris(hydrogen fluoride); fluorosulfonyl fluoride / acetonitrile / Cooling with ice
View Scheme
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
Stage #1: 2-C-methyl-D-ribono-1,4-lactone; benzoyl chloride With triethylamine In dichloromethane Cooling with ice;
Stage #2: With pyridine; trifluoromethylsulfonic anhydride In dichloromethane at -40 - 20℃; for 1h;
Stage #3: With triethylamine tris(hydrogen fluoride); triethylamine In acetonitrile Cooling with ice;
58%
(2R,3R,4R,5S)-5-(4-benzoylamino-2-oxopyrimidin-1(2H)-yl)-2-((benzoyloxy)methyl)-4-fluoro-4-methyltetrahydrofuran-3-yl benzoate

(2R,3R,4R,5S)-5-(4-benzoylamino-2-oxopyrimidin-1(2H)-yl)-2-((benzoyloxy)methyl)-4-fluoro-4-methyltetrahydrofuran-3-yl benzoate

((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 ammonium cerium (IV) nitrate In 1,4-dioxane for 6h; Solvent; Irradiation;52%
C6H9FO4

C6H9FO4

benzoyl chloride
98-88-4

benzoyl chloride

A

((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

B

((2R,3R,4S)-3-(benzoyloxy)-4-fluoro-4-methyl-5-oxotetrahydrofuran-2-yl)methylbenzoate
1157884-58-6

((2R,3R,4S)-3-(benzoyloxy)-4-fluoro-4-methyl-5-oxotetrahydrofuran-2-yl)methylbenzoate

Conditions
ConditionsYield
With pyridine optical yield given as %de;
C6H9FO4

C6H9FO4

benzoyl chloride
98-88-4

benzoyl chloride

A

((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

B

C20H17FO6

C20H17FO6

Conditions
ConditionsYield
With dmap; triethylamine In acetonitrile at 20 - 40℃;A 12.7 g
B n/a
(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

((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
Multi-step reaction with 4 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
4: pyridine / 0.5 h / 20 °C / Cooling with ice
View Scheme
Multi-step reaction with 4 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
4.1: pyridine / 0.75 h / 0 - 20 °C
View Scheme
Multi-step reaction with 4 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
4.1: triethylamine; dmap / acetonitrile / 2 h / 5 - 20 °C
View Scheme
Multi-step reaction with 3 steps
1.1: acetic acid / ethanol / 15 h / 80 °C
2.1: pyridine / 2-methyltetrahydrofuran / Inert atmosphere
2.2: 0.5 h / 5 - 15 °C
3.1: triethylamine; triethylamine tris(hydrogen fluoride) / acetonitrile
3.2: 2 h / 0 °C
View Scheme
C10H18O6
1351925-17-1

C10H18O6

((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
Multi-step reaction with 4 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
4: pyridine / 0.5 h / 20 °C / Cooling with ice
View Scheme
C11H18FO8S(1-)

C11H18FO8S(1-)

((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
Multi-step reaction with 3 steps
1: 2,2-dimethoxy-propane; hydrogenchloride; water / tetrahydrofuran / 3 h / 20 °C
2: hydrogenchloride; water / ethanol / 21 h / 20 °C
3: pyridine / 0.5 h / 20 °C / Cooling with ice
View Scheme
C11H19FO5
1033394-83-0

C11H19FO5

((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
Multi-step reaction with 2 steps
1: hydrogenchloride; water / ethanol / 21 h / 20 °C
2: pyridine / 0.5 h / 20 °C / Cooling with ice
View Scheme
C10H16FO8S(1-)

C10H16FO8S(1-)

((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
Multi-step reaction with 3 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
3: pyridine / 0.5 h / 20 °C / Cooling with ice
View Scheme
C10H17FO5

C10H17FO5

((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
Multi-step reaction with 2 steps
1: hydrogenchloride; water / ethanol / 18 h / 20 °C
2: pyridine / 0.5 h / 20 °C / Cooling with ice
View Scheme
(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

((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
Multi-step reaction with 2 steps
1: dihydrogen peroxide; lithium hydroxide monohydrate / tetrahydrofuran; water / 1 h / 0 - 5 °C
2: triethylamine; dmap / tetrahydrofuran / 2 h / 0 - 40 °C
View Scheme
(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

((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
Multi-step reaction with 2 steps
1: dihydrogen peroxide; lithium hydroxide monohydrate / tetrahydrofuran; water / 1 h / 0 - 5 °C
2: triethylamine; dmap / tetrahydrofuran / 2 h / 0 - 40 °C
View Scheme
(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

((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
Multi-step reaction with 2 steps
1: dihydrogen peroxide; lithium hydroxide monohydrate / tetrahydrofuran; water / 1 h / 0 - 5 °C
2: triethylamine; dmap / tetrahydrofuran / 2 h / 0 - 40 °C
View Scheme
C11H18O4
130606-67-6

C11H18O4

((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
Multi-step reaction with 5 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
5.1: pyridine / 0.75 h / 0 - 20 °C
View Scheme
Multi-step reaction with 5 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
5.1: triethylamine; dmap / acetonitrile / 2 h / 5 - 20 °C
View Scheme
(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

((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
Multi-step reaction with 3 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
3.1: pyridine / 0.75 h / 0 - 20 °C
View Scheme
Multi-step reaction with 3 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
3.1: triethylamine; dmap / acetonitrile / 2 h / 5 - 20 °C
View Scheme
Multi-step reaction with 4 steps
1.1: dmap / toluene / 12 h / 60 °C
2.1: tetraethylammonium fluoride / 1,4-dioxane / 16 h / 105 °C
2.2: 3 h / 20 °C
3.1: ethanol / 1 h / Reflux
4.1: hydrogenchloride / water; ethanol / 22 h / 20 °C
4.2: 1.17 h / 0 - 30 °C
View Scheme
C12H21FO4

C12H21FO4

((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
Multi-step reaction with 2 steps
1: water; hydrogenchloride / ethanol / 48 h / 20 °C
2: pyridine / 0.75 h / 0 - 20 °C
View Scheme
((2R,3R,4R)-3-(benzoyloxy)-4-methyl-5-oxo-4-(((trifluoromethyl)sulfonyl)oxy)tetrahydrofuran-2-yl)methylbenzoate

((2R,3R,4R)-3-(benzoyloxy)-4-methyl-5-oxo-4-(((trifluoromethyl)sulfonyl)oxy)tetrahydrofuran-2-yl)methylbenzoate

((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
Multi-step reaction with 2 steps
1: dichloromethane; water; dimethyl sulfoxide / Cooling with ice
2: triethylamine; triethylamine tris(hydrogen fluoride); fluorosulfonyl fluoride / acetonitrile / Cooling with ice
View Scheme
Multi-step reaction with 3 steps
1: water / 0.42 h
2: triethylamine / water; acetone / 45 °C
3: triethylamine; triethylamine tris(hydrogen fluoride); fluorosulfonyl fluoride / acetonitrile / Cooling with ice
View Scheme
Multi-step reaction with 2 steps
1: dimethyl sulfoxide / ethyl acetate
2: triethylamine tris(hydrogen fluoride); triethylamine / acetonitrile / Cooling with ice
View Scheme
Multi-step reaction with 3 steps
1: 0.5 h / 20 °C
2: triethylamine / acetone / 50 °C
3: triethylamine tris(hydrogen fluoride); triethylamine / acetonitrile / Cooling with ice
View Scheme
((3aR,4R,6aR)-2-(formyloxy)-6a-methyl-6-oxo-2-phenyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methylbenzoate

((3aR,4R,6aR)-2-(formyloxy)-6a-methyl-6-oxo-2-phenyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methylbenzoate

((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
Multi-step reaction with 2 steps
1: triethylamine / water; acetone / 45 °C
2: triethylamine; triethylamine tris(hydrogen fluoride); fluorosulfonyl fluoride / acetonitrile / Cooling with ice
View Scheme
Multi-step reaction with 2 steps
1: triethylamine / acetone / 50 °C
2: triethylamine tris(hydrogen fluoride); triethylamine / acetonitrile / Cooling with ice
View Scheme
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
Multi-step reaction with 4 steps
1.1: triethylamine / ethyl acetate / Cooling with ice
2.1: pyridine / dichloromethane / 0.08 h / -10 °C
2.2: 20 °C
3.1: dichloromethane; water; dimethyl sulfoxide / Cooling with ice
4.1: triethylamine; triethylamine tris(hydrogen fluoride); fluorosulfonyl fluoride / acetonitrile / Cooling with ice
View Scheme
Multi-step reaction with 5 steps
1.1: triethylamine / ethyl acetate / Cooling with ice
2.1: pyridine / dichloromethane / 0.08 h / -10 °C
2.2: 20 °C
3.1: water / 0.42 h
4.1: triethylamine / water; acetone / 45 °C
5.1: triethylamine; triethylamine tris(hydrogen fluoride); fluorosulfonyl fluoride / acetonitrile / Cooling with ice
View Scheme
Multi-step reaction with 2 steps
1.1: triethylamine / ethyl acetate / Cooling with ice
2.1: pyridine; trifluoromethylsulfonic anhydride / dichloromethane / 1 h / -40 - 20 °C
2.2: Cooling with ice
View Scheme
((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
Multi-step reaction with 4 steps
1.1: triethylamine / ethyl acetate / Cooling with ice
2.1: pyridine / dichloromethane / 0.08 h / -10 °C
2.2: 20 °C
3.1: dichloromethane; water; dimethyl sulfoxide / Cooling with ice
4.1: triethylamine; triethylamine tris(hydrogen fluoride); fluorosulfonyl fluoride / acetonitrile / Cooling with ice
View Scheme
Multi-step reaction with 5 steps
1.1: triethylamine / ethyl acetate / Cooling with ice
2.1: pyridine / dichloromethane / 0.08 h / -10 °C
2.2: 20 °C
3.1: water / 0.42 h
4.1: triethylamine / water; acetone / 45 °C
5.1: triethylamine; triethylamine tris(hydrogen fluoride); fluorosulfonyl fluoride / acetonitrile / Cooling with ice
View Scheme
Multi-step reaction with 2 steps
1.1: triethylamine / ethyl acetate / Cooling with ice
2.1: pyridine; trifluoromethylsulfonic anhydride / dichloromethane / 1 h / -40 - 20 °C
2.2: Cooling with ice
View Scheme
C18H22FNO6

C18H22FNO6

((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
Multi-step reaction with 2 steps
1: hydrogenchloride / water; ethanol / 4 h / Reflux
2: triethylamine; dmap / ethyl acetate / 2 h / -5 °C
View Scheme
C10H17FO5

C10H17FO5

((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
Multi-step reaction with 2 steps
1.1: dmap; triethylamine / water; acetonitrile; ethyl acetate / 1 h / 0 - 20 °C / Inert atmosphere; Cooling with ice
1.2: 0.5 h / 0 °C / Inert atmosphere
2.1: Selectfluor / N,N-dimethyl-formamide / 1 h / -40 - 20 °C
View Scheme
C25H29FO6Si

C25H29FO6Si

methyl iodide
74-88-4

methyl iodide

((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 Selectfluor In N,N-dimethyl-formamide at -40 - 20℃; for 1h;3.5 g
((2R,3R,4R)-3-(benzoyloxy)-4-methyl-4-((methylsulfonyl)oxy)-5-oxotetrahydrofuran-2-yl)methylbenzoate

((2R,3R,4R)-3-(benzoyloxy)-4-methyl-4-((methylsulfonyl)oxy)-5-oxotetrahydrofuran-2-yl)methylbenzoate

((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
Multi-step reaction with 2 steps
1: tetra-(n-butyl)ammonium iodide; potassium nitrite / dimethyl sulfoxide; water / 75 °C
2: triethylamine tris(hydrogen fluoride); triethylamine / acetonitrile / Cooling with ice
View Scheme
((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

((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
With lithium tri-t-butoxyaluminum hydride In tetrahydrofuran Inert atmosphere;100%
Stage #1: ((2R,3R,4R)-3-benzoyloxy-4-fluoro-4-methyl-5-oxo-tetrahydrofuran-2-yl)methyl benzoate With lithium tri-t-butoxyaluminum hydride In tetrahydrofuran at -10 - 0℃; Inert atmosphere;
Stage #2: With water; ammonium chloride In tetrahydrofuran Inert atmosphere;
99%
With lithium tri-t-butoxyaluminum hydride In tetrahydrofuran at 0℃; for 3h;99%
((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;
((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

((2R,3R,4R,5R)-3-(benzoyloxy)-4-fluoro-5-hydroxy-4-methyltetrahydrofuran-2-yl)methyl benzoate
1199809-22-7

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

Conditions
ConditionsYield
In tetrahydrofuran; toluene at -10 - -5℃; for 3h; Inert atmosphere;90%
Stage #1: ((2R,3R,4R)-3-benzoyloxy-4-fluoro-4-methyl-5-oxo-tetrahydrofuran-2-yl)methyl benzoate With lithium tri-t-butoxyaluminum hydride In tetrahydrofuran at -30 - -10℃; for 1.25h; Inert atmosphere;
Stage #2: With ammonium chloride In tetrahydrofuran; ethyl acetate at 0℃;
77%
With lithium tri(tert-butoxy)aluminum hydride In tetrahydrofuran at -30 - -10℃; for 2.25h; Inert atmosphere;77%
With aluminium In dichloromethane; 2,2,2-trifluoroethanol; toluene at 0 - 10℃;
With lithium tri-(tert-butoxy)aluminum hydride In tetrahydrofuran at -20℃; Inert atmosphere;
((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

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

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

Conditions
ConditionsYield
With sodium bis(2-methoxyethoxy)aluminium dihydride In tetrahydrofuran; toluene at -10 - -5℃; for 3h; Inert atmosphere;90%
((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

(2R)-2-deoxy-2-fluoro-2-methyl-α/β-D-erythro-pentofuranosyl chloride-3,5-dibenzoate

(2R)-2-deoxy-2-fluoro-2-methyl-α/β-D-erythro-pentofuranosyl chloride-3,5-dibenzoate

Conditions
ConditionsYield
Stage #1: ((2R,3R,4R)-3-benzoyloxy-4-fluoro-4-methyl-5-oxo-tetrahydrofuran-2-yl)methyl benzoate With 2,2,2-trifluoroethanol; sodium bis(2-methoxyethoxy)aluminium dihydride In acetic acid butyl ester; toluene at -20 - -15℃;
Stage #2: With sulfuryl dichloride; tetrabutylammomium bromide In acetic acid butyl ester; toluene at -20 - 20℃;
86%
Multi-step reaction with 2 steps
1: sodium bis-(2-methoxyethoxy) (2,2,2,trifluoroethoxy) aluminum hydride / toluene; acetic acid butyl ester / -20 - -15 °C
2: tetrabutylammomium bromide; sulfuryl dichloride / toluene; acetic acid butyl ester / 1 h / -20 - 0 °C
View Scheme
Stage #1: ((2R,3R,4R)-3-benzoyloxy-4-fluoro-4-methyl-5-oxo-tetrahydrofuran-2-yl)methyl benzoate In dichloromethane at -10℃; for 0.5h;
Stage #2: With sulfuryl dichloride; tetrabutylammomium bromide In dichloromethane at -10 - 20℃; for 16h;
((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

7-bromo-2,4-bis(methylthio)imidazo[2,1-f][1,2,4]triazine
1062135-87-8

7-bromo-2,4-bis(methylthio)imidazo[2,1-f][1,2,4]triazine

C27H25FN4O6S2

C27H25FN4O6S2

Conditions
ConditionsYield
Stage #1: 7-bromo-2,4-bis(methylthio)imidazo[2,1-f][1,2,4]triazine With n-butyllithium In tetrahydrofuran; hexanes at -78℃; for 0.0833333h;
Stage #2: ((2R,3R,4R)-3-benzoyloxy-4-fluoro-4-methyl-5-oxo-tetrahydrofuran-2-yl)methyl benzoate With boron trifluoride diethyl etherate In tetrahydrofuran at -78℃; for 2h;
67%
Stage #1: 7-bromo-2,4-bis(methylthio)imidazo[2,1-f][1,2,4]triazine With n-butyllithium In tetrahydrofuran; hexane at -78℃;
Stage #2: ((2R,3R,4R)-3-benzoyloxy-4-fluoro-4-methyl-5-oxo-tetrahydrofuran-2-yl)methyl benzoate With boron trifluoride diethyl etherate In tetrahydrofuran; hexane at -78℃; for 2h;
Stage #3: With ammonium chloride In tetrahydrofuran; hexane
67%
((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

(((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
Stage #1: ((2R,3R,4R)-3-benzoyloxy-4-fluoro-4-methyl-5-oxo-tetrahydrofuran-2-yl)methyl benzoate With lithium tri-t-butoxyaluminum hydride In tetrahydrofuran at -30 - -15℃; for 1.5h; Inert atmosphere;
Stage #2: With carbon tetrabromide; triphenylphosphine In tetrahydrofuran; dichloromethane at -20 - 0℃; for 2.16h; Inert atmosphere;
62%
With lithium tri-(tert-butoxy)aluminum hydride In tetrahydrofuran; ethyl acetate at -30 - -15℃; for 1.5h; Inert atmosphere;62%
Multi-step reaction with 2 steps
1: lithium tri-t-butoxyaluminum hydride / tetrahydrofuran / 0.67 h / -30 - -15 °C / Inert atmosphere
2: carbon tetrabromide; triphenylphosphine / dichloromethane / 1.75 h / -20 - -15 °C / Inert atmosphere
View Scheme
((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

7-bromo-pyrrolo[2,1-f][1,2,4]triazin-4-ylamine
937046-98-5

7-bromo-pyrrolo[2,1-f][1,2,4]triazin-4-ylamine

C26H23FN4O6

C26H23FN4O6

Conditions
ConditionsYield
Stage #1: 7-bromo-pyrrolo[2,1-f][1,2,4]triazin-4-ylamine With n-butyllithium In tetrahydrofuran; hexanes at -78℃; for 0.5h;
Stage #2: With 1,2-bis-(chlorodimethylsilyl)ethane In tetrahydrofuran for 0.75h;
Stage #3: ((2R,3R,4R)-3-benzoyloxy-4-fluoro-4-methyl-5-oxo-tetrahydrofuran-2-yl)methyl benzoate Product distribution / selectivity;
40%
Stage #1: 7-bromo-pyrrolo[2,1-f][1,2,4]triazin-4-ylamine With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.5h; Inert atmosphere;
Stage #2: ((2R,3R,4R)-3-benzoyloxy-4-fluoro-4-methyl-5-oxo-tetrahydrofuran-2-yl)methyl benzoate With 1,2-bis-(chlorodimethylsilyl)ethane In tetrahydrofuran; hexane; water at -78℃; for 3.75h; Inert atmosphere;
Stage #3: With ammonium chloride; acetic acid In tetrahydrofuran; hexane Product distribution / selectivity;
40%
((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

Tebbe's reagent

Tebbe's reagent

C21H19FO5

C21H19FO5

Conditions
ConditionsYield
With pyridine In tetrahydrofuran at -40℃; for 1h; Tebbe Olefination;20%
((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

7-bromopyrrolo[2,1-f][1,2,4]triazin-4-ylamine
1238579-07-1

7-bromopyrrolo[2,1-f][1,2,4]triazin-4-ylamine

C27H23FN2O6S2

C27H23FN2O6S2

Conditions
ConditionsYield
Stage #1: 7-bromopyrrolo[2,1-f][1,2,4]triazin-4-ylamine With n-butyllithium In tetrahydrofuran; hexane at -78℃;
Stage #2: ((2R,3R,4R)-3-benzoyloxy-4-fluoro-4-methyl-5-oxo-tetrahydrofuran-2-yl)methyl benzoate In tetrahydrofuran; hexane at -78℃;
((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

C27H25FN4O5S2
1273029-03-0

C27H25FN4O5S2

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: n-butyllithium / tetrahydrofuran; hexanes / 0.08 h / -78 °C
1.2: 2 h / -78 °C
2.1: boron trifluoride diethyl etherate; triethylsilane / dichloromethane / 184 h / 20 °C
View Scheme
((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

C12H16FN5O3S
1273029-04-1

C12H16FN5O3S

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: n-butyllithium / tetrahydrofuran; hexanes / 0.08 h / -78 °C
1.2: 2 h / -78 °C
2.1: boron trifluoride diethyl etherate; triethylsilane / dichloromethane / 184 h / 20 °C
3.1: ammonia / 16 h / 50 °C / Sealed tube
3.2: 0.67 h / 60 °C
View Scheme
((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

C12H16FN5O5S
1273029-05-2

C12H16FN5O5S

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: n-butyllithium / tetrahydrofuran; hexanes / 0.08 h / -78 °C
1.2: 2 h / -78 °C
2.1: boron trifluoride diethyl etherate; triethylsilane / dichloromethane / 184 h / 20 °C
3.1: ammonia / 16 h / 50 °C / Sealed tube
3.2: 0.67 h / 60 °C
4.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 16 h / 20 °C
View Scheme
((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

C11H15FN6O3
1273029-06-3

C11H15FN6O3

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: n-butyllithium / tetrahydrofuran; hexanes / 0.08 h / -78 °C
1.2: 2 h / -78 °C
2.1: boron trifluoride diethyl etherate; triethylsilane / dichloromethane / 184 h / 20 °C
3.1: ammonia / 16 h / 50 °C / Sealed tube
3.2: 0.67 h / 60 °C
4.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 16 h / 20 °C
5.1: ammonia / 72 h / 115 °C / Sealed tube
View Scheme
((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

C11H14FN5O4
1273029-07-4

C11H14FN5O4

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: n-butyllithium / tetrahydrofuran; hexanes / 0.08 h / -78 °C
1.2: 2 h / -78 °C
2.1: boron trifluoride diethyl etherate; triethylsilane / dichloromethane / 184 h / 20 °C
3.1: ammonia / 16 h / 50 °C / Sealed tube
3.2: 0.67 h / 60 °C
4.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 16 h / 20 °C
5.1: ammonia / 72 h / 115 °C / Sealed tube
6.1: water / bovine spleen type IX sdenosine deaminase A5168 / 4 h / 37 °C / Enzymatic reaction
View Scheme
((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

C27H22FN5O5
1272971-36-4

C27H22FN5O5

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: n-butyllithium / tetrahydrofuran; hexanes / 0.5 h / -78 °C
1.2: 0.75 h
2.1: trimethylsilyl trifluoromethanesulfonate / acetonitrile / 73 h / 20 - 65 °C
View Scheme
((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

(2R,3R,4R,5R)-2-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-3-fluoro-4-hydroxy-5-(hydroxymethyl)-3-methyltetrahydrofuran-2-carbonitrile
1273029-08-5

(2R,3R,4R,5R)-2-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-3-fluoro-4-hydroxy-5-(hydroxymethyl)-3-methyltetrahydrofuran-2-carbonitrile

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: n-butyllithium / tetrahydrofuran; hexanes / 0.5 h / -78 °C
1.2: 0.75 h
2.1: trimethylsilyl trifluoromethanesulfonate / acetonitrile / 73 h / 20 - 65 °C
3.1: water; ammonia / methanol / 16 h / 20 °C
View Scheme
((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

C12H15FN4O4

C12H15FN4O4

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: n-butyllithium / tetrahydrofuran; hexanes / 0.5 h / -78 °C
1.2: 0.75 h
2.1: water; ammonia / methanol / 16 h / 20 °C
View Scheme
((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

C11H17FN5O13P3
1273029-12-1

C11H17FN5O13P3

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1.1: n-butyllithium / tetrahydrofuran; hexanes / 0.08 h / -78 °C
1.2: 2 h / -78 °C
2.1: boron trifluoride diethyl etherate; triethylsilane / dichloromethane / 184 h / 20 °C
3.1: ammonia / 16 h / 50 °C / Sealed tube
3.2: 0.67 h / 60 °C
4.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 16 h / 20 °C
5.1: ammonia / 72 h / 115 °C / Sealed tube
6.1: water / bovine spleen type IX sdenosine deaminase A5168 / 4 h / 37 °C / Enzymatic reaction
7.1: trichlorophosphate; trimethyl phosphite / 0 °C
View Scheme
((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

C25H40FN6O8PS2
1273029-18-7

C25H40FN6O8PS2

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1.1: n-butyllithium / tetrahydrofuran; hexanes / 0.08 h / -78 °C
1.2: 2 h / -78 °C
2.1: boron trifluoride diethyl etherate; triethylsilane / dichloromethane / 184 h / 20 °C
3.1: ammonia / 16 h / 50 °C / Sealed tube
3.2: 0.67 h / 60 °C
4.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 16 h / 20 °C
5.1: ammonia / 72 h / 115 °C / Sealed tube
6.1: 1H-tetrazole; phosphorous acid trimethyl ester / 2 h / 0 °C
7.1: dihydrogen peroxide / water / 0.5 h / 0 - 20 °C
View Scheme
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