D-erythro-Pentonic acid, 2-deoxy-2-fluoro-2-methyl-, γ-lactone, 3,5-dibenzoate, (2R)- supplier

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

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

Conditions

Conditions	Yield
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;

: 1033394-83-0
C11H19FO5

: 98-88-4
benzoyl chloride

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

Conditions

Conditions	Yield
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

: 98-88-4
benzoyl chloride

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

Conditions

Conditions	Yield
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

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

Conditions

Conditions	Yield
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%

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

: 98-88-4
benzoyl chloride

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

Conditions

Conditions	Yield
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%

: 729596-46-7
3,5-di-O-benzoyl-2-C-methyl-D-ribono-γ-lactone

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

Conditions

Conditions	Yield
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

: 492-30-8, 7306-56-1, 19774-08-4, 36791-96-5, 36791-97-6, 53008-90-5, 53008-96-1, 53008-97-2, 86204-17-3, 86204-18-4, 93636-22-7
2-C-methyl-D-ribono-1,4-lactone

: 98-88-4
benzoyl chloride

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

Conditions

Conditions	Yield
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

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

Conditions

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

: C6H9FO4

: 98-88-4
benzoyl chloride

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

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

Conditions

Conditions	Yield
With pyridine optical yield given as %de;

...Expand

: C6H9FO4

: 98-88-4
benzoyl chloride

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

B: C20H17FO6

Conditions

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

...Expand

: 93635-76-8
(2S,3R)-3-[(4R)-2,2-dimethyl-[1,3]dioxolane-4-yl]-2,3-dihydroxy-2-methylpropionic acid ethyl ester

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

Conditions

Conditions	Yield
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

: 1351925-17-1
C10H18O6

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

Conditions

Conditions	Yield
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-)

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

Conditions

Conditions	Yield
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

: 1033394-83-0
C11H19FO5

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

Conditions

Conditions	Yield
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-)

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

Conditions

Conditions	Yield
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

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

Conditions

Conditions	Yield
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

: 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

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

Conditions

Conditions	Yield
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

: 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

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

Conditions

Conditions	Yield
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

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

Conditions

Conditions	Yield
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

: 130606-67-6
C11H18O4

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

Conditions

Conditions	Yield
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

Yield

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

: 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

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

Conditions

Conditions	Yield
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

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

Conditions

Conditions	Yield
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

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

Conditions

Conditions	Yield
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

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

Conditions

Conditions	Yield
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

: 98-88-4
benzoyl chloride

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

Conditions

Conditions	Yield
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

: 492-30-8, 7306-56-1, 19774-08-4, 36791-96-5, 36791-97-6, 53008-90-5, 53008-96-1, 53008-97-2, 86204-17-3, 86204-18-4, 93636-22-7
2-C-methyl-D-ribono-1,4-lactone

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

Conditions

Conditions	Yield
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

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

Conditions

Conditions	Yield
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

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

Conditions

Conditions	Yield
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

: 74-88-4
methyl iodide

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

Conditions

Conditions	Yield
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

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

Conditions

Conditions	Yield
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

: 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

Conditions

Conditions	Yield
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%

: 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

Conditions	Yield
With methanesulfonic acid In ethanol for 5h; Reagent/catalyst; Solvent; Reflux;	95.3%
With sodium methylate In methanol at 20℃; for 2h;

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

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

Conditions

Conditions	Yield
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;

: 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

Conditions

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

: 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

Conditions

Conditions	Yield
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;

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

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

: C27H25FN4O6S2

Conditions

Conditions	Yield
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%

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

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

Conditions

Conditions	Yield
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

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

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

: C26H23FN4O6

Conditions

Conditions	Yield
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%

Yield

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%

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

: Tebbe's reagent

: C21H19FO5

Conditions

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

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

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

: C27H23FN2O6S2

Conditions

Conditions	Yield
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℃;

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

: 1273029-03-0
C27H25FN4O5S2

Conditions

Conditions	Yield
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

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

: 1273029-04-1
C12H16FN5O3S

Conditions

Conditions	Yield
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

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

: 1273029-05-2
C12H16FN5O5S

Conditions

Conditions	Yield
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

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

: 1273029-06-3
C11H15FN6O3

Conditions

Conditions	Yield
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

Yield

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

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

: 1273029-07-4
C11H14FN5O4

Conditions

Conditions	Yield
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

Yield

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

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

: 1272971-36-4
C27H22FN5O5

Conditions

Conditions	Yield
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

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

: 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

Conditions	Yield
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

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

: C12H15FN4O4

Conditions

Conditions	Yield
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

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

: 1273029-12-1
C11H17FN5O13P3

Conditions

Conditions	Yield
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

Yield

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

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

: 1273029-18-7
C25H40FN6O8PS2

Conditions

Conditions	Yield
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

Yield

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

Product Name

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

Synthetic route

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