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Basic Information
CAS No.: 97614-43-2
Name: 2-Deoxy-2-fluoro-1,3,5-tri-O-benzoyl-D-ribofuranose
Article Data: 12
Molecular Structure:
Molecular Structure of 97614-43-2 (2-Deoxy-2-fluoro-1,3,5-tri-O-benzoyl-D-ribofuranose)
Formula: C26H21FO7
Molecular Weight: 464.447
Synonyms: a-D-Arabinofuranose,2-deoxy-2-fluoro-, tribenzoate (9CI);2'-Fluoro-2'-deoxy-1,3,5-tri-O-benzoyl-a-D-arabinofuranose;1,3,5-Tri-O-benzoyl-2-deoxy-2-fluoro-α-D-arabinose;
EINECS: 619-281-1
Density: 1.35 g/cm3
Melting Point: 74-77°C
Boiling Point: 584.1 °C at 760 mmHg
Flash Point: 295.7 °C
Safety: 24/25
PSA: 88.13000
LogP: 3.98900
Related products
Synthetic route
97614-41-0

2-O-<(trifluoromethyl)sulfonyl>-1,3,5-tri-O-benzoyl-α-D-ribofuranose

97614-43-2

1,3,5-tri-O-benzoyl-2-deoxy-2-fluoro-α-D-arabinofuranose

Conditions
ConditionsYield
With triethylamine tris(hydrogen fluoride) In ethyl acetate at 80℃; for 24h; Substitution;85%
With triethylamine tris(hydrogen fluoride); triethylamine In acetonitrile at 50℃; for 18h;
With hydrogen fluoride; tetrabutylammonium bicarbonate In acetonitrile at 80℃; for 0.5h;
22224-41-5

1,3,5-tri-O-benzoyl-α-D-ribofuranoside

97614-43-2

1,3,5-tri-O-benzoyl-2-deoxy-2-fluoro-α-D-arabinofuranose

Conditions
ConditionsYield
With (bis-(2-methoxyethyl)amino)sulfur trufluoride In dichloromethane at 50℃;83%
With diethylamino-sulfur trifluoride In dichloromethane at 40℃;75%
Multi-step reaction with 2 steps
1: pyridine / acetonitrile / 0.5 h / 20 °C
2: Et3N(HF)3; Et3N / acetonitrile / 18 h / 50 °C
View Scheme
Multi-step reaction with 2 steps
1: 100 percent / CH2Cl2; pyridine / -10 °C
2: 85 percent / Et3N*3HF / ethyl acetate / 24 h / 80 °C
View Scheme
With diethylamino-sulfur trifluoride
97614-42-1

2-O-(imidazolylsulfonyl)-1,3,5-tri-O-benzoyl-α-D-ribofuranose

97614-43-2

1,3,5-tri-O-benzoyl-2-deoxy-2-fluoro-α-D-arabinofuranose

Conditions
ConditionsYield
With triethylamine tris(hydrogen fluoride) In ethyl acetate at 60 - 70℃; for 4.5h;66.4%
Multi-step reaction with 2 steps
1: 77 percent / Et3N*HF / ethyl acetate
2: (But)4NF / ethyl acetate / 0.33 h / 70 °C
View Scheme
Multi-step reaction with 2 steps
1: Et3N*3HF / ethyl acetate / 20 - 60 °C
2: Et3N*3HF / ethyl acetate / 70 °C
View Scheme
97614-42-1

2-O-(imidazolylsulfonyl)-1,3,5-tri-O-benzoyl-α-D-ribofuranose

A

97614-43-2

1,3,5-tri-O-benzoyl-2-deoxy-2-fluoro-α-D-arabinofuranose

B

97614-50-1

2-O-(fluorosulfonyl)-1,3,5-tri-O-benzoyl-α-D-ribofuranose

Conditions
ConditionsYield
With potassium hydrogen bifluoride; hydrogen fluoride In various solvent(s) at 160℃; for 1h;A 62.8%
B n/a
97614-50-1

2-O-(fluorosulfonyl)-1,3,5-tri-O-benzoyl-α-D-ribofuranose

A

97614-43-2

1,3,5-tri-O-benzoyl-2-deoxy-2-fluoro-α-D-arabinofuranose

B

1,3,5-tri-O-benzoyl-α-D-arabinofuranose

Conditions
ConditionsYield
With hydrogen fluoride; triethylamine In ethyl acetate at 71 - 72℃; for 4h; Product distribution; Further Variations:; Reagents; Solvents; reaction time; Substitution;A 60.5%
B n/a
97614-41-0

2-O-<(trifluoromethyl)sulfonyl>-1,3,5-tri-O-benzoyl-α-D-ribofuranose

A

97614-43-2

1,3,5-tri-O-benzoyl-2-deoxy-2-fluoro-α-D-arabinofuranose

B

1,3,5-tri-O-benzoyl-α-D-arabinofuranose

Conditions
ConditionsYield
With tetrabutyl ammonium fluoride In ethyl acetate at 71 - 72℃; for 0.333333h; Substitution;A 34%
B n/a
107-21-1

ethylene glycol

97614-42-1

2-O-(imidazolylsulfonyl)-1,3,5-tri-O-benzoyl-α-D-ribofuranose

A

38491-60-0

β-phenyl hydroxypropionate

B

97614-43-2

1,3,5-tri-O-benzoyl-2-deoxy-2-fluoro-α-D-arabinofuranose

C

97614-49-8

C28H26O9

Conditions
ConditionsYield
With potassium hydrogen bifluoride; hydrogen fluoride In various solvent(s) at 160℃; for 1h; Product distribution; other reaction conditions;
...Expand
97614-50-1

2-O-(fluorosulfonyl)-1,3,5-tri-O-benzoyl-α-D-ribofuranose

97614-43-2

1,3,5-tri-O-benzoyl-2-deoxy-2-fluoro-α-D-arabinofuranose

Conditions
ConditionsYield
With triethylamine tris(hydrogen fluoride) In ethyl acetate at 70℃; Yield given;
With tetrabutyl ammonium fluoride In ethyl acetate at 70℃; for 0.333333h; Substitution;
97614-43-2

1,3,5-tri-O-benzoyl-2-deoxy-2-fluoro-α-D-arabinofuranose

97614-44-3

2-deoxy-2-fluoro-3,5-di-O-benzoyl-α-D-arabinofuranosyl bromide

Conditions
ConditionsYield
With hydrogen bromide; acetic acid In dichloromethane at -5 - 20℃; for 18.33h; Inert atmosphere;100%
With hydrogen bromide; acetic acid In dichloromethane for 20h; Ambient temperature;99%
With hydrogen bromide; acetic acid In dichloromethane at 20℃;99%
97614-43-2

1,3,5-tri-O-benzoyl-2-deoxy-2-fluoro-α-D-arabinofuranose

98855-71-1

((2R,3R,4S)-3-(benzoyloxy)-5-bromo-4-fluorotetrahydrofuran-2-yl)methyl benzoate

Conditions
ConditionsYield
With hydrogen bromide; acetic acid99%
With hydrogen bromide; acetic acid In dichloromethane at 20℃;99%
With acetic acid
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Chemistry

Molecular Structure of 2-Deoxy-2-fluoro-1,3,5-tri-O-benzoyl-D-ribofuranose (CAS NO. 97614-43-2):

IUPAC Name: [(2S,3S,4S)-5-Benzoyloxy-2-(benzoyloxymethyl)-4-fluorooxolan-3-yl] benzoate 
Molecular Formula: C26H21FO7
Molecular Weight: 464.439143 g/mol
XLogP3-AA: 5.2
H-Bond Donor: 0
H-Bond Acceptor: 8
Canonical SMILES: C1=CC=C(C=C1)C(=O)OCC2C(C(C(O2)OC(=O)C3=CC=CC=C3)F)OC(=O)C4=CC=CC=C4
Isomeric SMILES: C1=CC=C(C=C1)C(=O)OC[C@H]2[C@@H]([C@@H](C(O2)OC(=O)C3=CC=CC=C3)F)OC(=O)C4=CC=CC=C4
InChI: InChI=1S/C26H21FO7/c27-21-22(33-24(29)18-12-6-2-7-13-18)20(16-31-23(28)17-10-4-1-5-11-17)32-26(21)34-25(30)19-14-8-3-9-15-19/h1-15,20-22,26H,16H2/t20-,21-,22-,26?/m0/s1
InChIKey: JOAHVPNLVYCSAN-GAUDMLSGSA-N
Index of Refraction: 1.606
Molar Refractivity: 118.52 cm3
Molar Volume: 343.3 cm3
Surface Tension: 56.2 dyne/cm
Density: 1.35 g/cm3
Flash Point: 295.7 °C
Enthalpy of Vaporization: 87.29 kJ/mol
Boiling Point: 584.1 °C at 760 mmHg
Vapour Pressure: 1.24E-13 mmHg at 25 °C
Storage Temp.: 2-8 °C

Safety Profile

Safety Information of 2-Deoxy-2-fluoro-1,3,5-tri-O-benzoyl-D-ribofuranose (CAS NO. 97614-43-2):
WGK Germany: 3

Specification

  2-Deoxy-2-fluoro-1,3,5-tri-O-benzoyl-D-ribofuranose with cas registry number of 97614-43-2 is also called for 1,3,5-Tri-O-benzoyl-2-deoxy-2-fluoro-alpha-D-arabinofuranose ; alpha-D-arabinofuranose, 2-deoxy-2-fluoro-, tribenzoate .