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Cas Database |
| Name |
D-erythro-Pentonic acid, 2-deoxy-2-fluoro-2-methyl-, γ-lactone, 3,5-dibenzoate, (2R)- |
EINECS | 618-021-4 |
| CAS No. | 874638-80-9 | Density | 1.33 |
| PSA | 78.90000 | LogP | 2.72260 |
| Solubility | N/A | Melting Point |
133 oC |
| Formula | C20H17FO6 | Boiling Point | 458.6±34.0 °C(Predicted) |
| Molecular Weight | 372.35 | Flash Point | N/A |
| Transport Information | N/A | Appearance | N/A |
| Safety | Risk Codes | N/A | |
| Molecular Structure |
|
Hazard Symbols | N/A |
| Synonyms |
[(2R,3R,4R)-3-benzoyloxy-4-fluoro-4-methyl-5-oxooxolan-2-yl]methyl benzoate;; |
Article Data | 27 |
D-erythro-Pentonic acid, 2-deoxy-2-fluoro-2-methyl-, γ-lactone, 3,5-dibenzoate, (2R)- Synthetic route
- 874638-80-9
((2R,3R,4R)-3-benzoyloxy-4-fluoro-4-methyl-5-oxo-tetrahydrofuran-2-yl)methyl benzoate
| 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 | 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% |
- 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 | 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% |
- 874638-80-9
((2R,3R,4R)-3-benzoyloxy-4-fluoro-4-methyl-5-oxo-tetrahydrofuran-2-yl)methyl benzoate
| 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 | 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 | 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 |
- 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 | 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% |
- 874638-80-9
((2R,3R,4R)-3-benzoyloxy-4-fluoro-4-methyl-5-oxo-tetrahydrofuran-2-yl)methyl benzoate
| Conditions | Yield |
|---|---|
| With ammonium cerium (IV) nitrate In 1,4-dioxane for 6h; Solvent; Irradiation; | 52% |
- 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 | Yield |
|---|---|
| With pyridine optical yield given as %de; |
- 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
| Conditions | Yield |
|---|---|
| With dmap; triethylamine In acetonitrile at 20 - 40℃; | A 12.7 g B n/a |
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