2-Deoxy-2-fluoro-1,3,5-tri-O-benzoyl-D-ribofuranose supplier

Name
2-Deoxy-2-fluoro-1,3,5-tri-O-benzoyl-D-ribofuranose
EINECS 619-281-1
CAS No. 97614-43-2
Article Data12
CAS DataBase
Density 1.35 g/cm³
Solubility
Melting Point 74-77°C
Formula C₂₆H₂₁FO₇
Boiling Point 584.1 °C at 760 mmHg
Molecular Weight 464.447
Flash Point 295.7 °C
Transport Information
Appearance
Safety 24/25
Risk Codes
Molecular Structure
Hazard Symbols
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;
PSA 88.13000
LogP 3.98900

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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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: Et3N3HF / ethyl acetate / 20 - 60 °C 2: Et3N3HF / 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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
With hydrogen bromide; acetic acid	99%
With hydrogen bromide; acetic acid In dichloromethane at 20℃;	99%
With acetic acid

: 75-09-2
dichloromethane

: 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

Conditions	Yield
With hydrogen bromide; acetic acid	90%

: 97614-43-2
1,3,5-tri-O-benzoyl-2-deoxy-2-fluoro-α-D-arabinofuranose

: 28523-86-6
sevoflurane

Conditions

Conditions	Yield
With potassium fluoride In various solvent(s) at 95℃; for 1h; Substitution;	71%

: 111-87-5
octanol

: 97614-43-2
1,3,5-tri-O-benzoyl-2-deoxy-2-fluoro-α-D-arabinofuranose

A: octyl 2-deoxy-2-fluoro-3,5-di-O-benzoyl-β-D-arabinofuranoside

B: 1131273-34-1
octyl 2-deoxy-2-fluoro-3,5-di-O-benzoyl-α-D-arabinofuranoside

Conditions

Conditions	Yield
Stage #1: 1,3,5-tri-O-benzoyl-2-deoxy-2-fluoro-α-D-arabinofuranose With tin(IV) chloride In acetonitrile at 20℃; for 0.25h; Molecular sieve; Inert atmosphere; Stage #2: octanol In acetonitrile at 20℃; for 1.5h; Inert atmosphere; Stage #3: With triethylamine In dichloromethane	A n/a B 54%

...Expand

: 97614-43-2
1,3,5-tri-O-benzoyl-2-deoxy-2-fluoro-α-D-arabinofuranose

: 75788-35-1
9-Trimethylsilyl-2,6-dichlorpurin

A: C24H17Cl2FN4O5

B: C24H17Cl2FN4O5

C: 329187-80-6
((2R,3R,4S,5R)-3-(benzoyloxy)-5-(2,6-dichloro-9H-purin-9-yl)-4-fluorotetrahydrofuran-2-yl)methyl benzoate

D: 329187-81-7
C24H17Cl2FN4O5

Conditions

Conditions	Yield
With trimethylsilyl trifluoromethanesulfonate In acetonitrile for 0.333333h; Heating;	A 5% B n/a C 35% D 33%

...Expand

: 97614-43-2
1,3,5-tri-O-benzoyl-2-deoxy-2-fluoro-α-D-arabinofuranose

: 60855-35-8
6-benzoylamino-9-trimethylsilylpurine

A: 20187-82-0, 20227-41-2, 64183-27-3, 123334-75-8
9-(2-deoxy-2-fluoro-β-D-arabinofuranosyl)adenine

B: 20187-82-0
9-(2-deoxy-2-fluoro-α-D-arabinofuranosyl)adenine

C: 7-(2-deoxy-2-fluoro-α-D-arabinofuranosyl)adenine

Conditions

Conditions	Yield
Stage #1: 1,3,5-tri-O-benzoyl-2-deoxy-2-fluoro-α-D-arabinofuranose; 6-benzoylamino-9-trimethylsilylpurine With trimethylsilyl trifluoromethanesulfonate In acetonitrile for 4h; Heating; Stage #2: With ammonia In methanol at 20℃; for 48h;	A 14% B 14% C 25%

...Expand

: 97614-43-2
1,3,5-tri-O-benzoyl-2-deoxy-2-fluoro-α-D-arabinofuranose

: 7288-28-0
2,4-bis(trimethylsiloxy)-5-methylpyrimidine

: C23H19FN2O7

Conditions

Conditions	Yield
With tin(IV) chloride In acetonitrile at 80 - 81℃; for 0.75h;

: 97614-43-2
1,3,5-tri-O-benzoyl-2-deoxy-2-fluoro-α-D-arabinofuranose

: 909101-48-0
4-amino-7-(2-deoxy-2-fluoro-β-D-arabinofuranosyl)-5-fluoro-7H-pyrrolo[2,3-d]pyrimidine

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: HBr; AcOH / CH2Cl2 / 16 h / 20 °C 2.1: KOH; tris[2-(2-methoxyethoxy)ethyl]amine / acetonitrile / 0.25 h / 20 °C 2.2: 61.7 percent / acetonitrile / 0.17 h / 20 °C 3.1: 72 percent / aq. NH3 / dioxane / 16 h / 120 °C View Scheme

: 97614-43-2
1,3,5-tri-O-benzoyl-2-deoxy-2-fluoro-α-D-arabinofuranose

: 909101-50-4
7-(2-deoxy-2-fluoro-β-D-arabinofuranosyl)-5-fluoro-4-methoxy-7H-pyrrolo[2,3-d]pyrimidine

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: HBr; AcOH / CH2Cl2 / 16 h / 20 °C 2.1: KOH; tris[2-(2-methoxyethoxy)ethyl]amine / acetonitrile / 0.25 h / 20 °C 2.2: 61.7 percent / acetonitrile / 0.17 h / 20 °C 3.1: 97 percent / NaOMe / 12 h / 20 °C View Scheme

: 97614-43-2
1,3,5-tri-O-benzoyl-2-deoxy-2-fluoro-α-D-arabinofuranose

: 7-(2-deoxy-2-fluoro-β-D-arabinofuranosyl)-3,7-dihydro-5-fluoro-4H-pyrrolo[2,3-d]pyrimidin-4-one

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1.1: HBr; AcOH / CH2Cl2 / 16 h / 20 °C 2.1: KOH; tris[2-(2-methoxyethoxy)ethyl]amine / acetonitrile / 0.25 h / 20 °C 2.2: 61.7 percent / acetonitrile / 0.17 h / 20 °C 3.1: 97 percent / NaOMe / 12 h / 20 °C 4.1: 37 percent / aq. NaOH / 1 h / Heating View Scheme

: 97614-43-2
1,3,5-tri-O-benzoyl-2-deoxy-2-fluoro-α-D-arabinofuranose

: 909101-46-8
4-chloro-7-(2-deoxy-3,5-di-O-benzoyl-β-D-arabinofuranosyl)-5-fluoro-7H-pyrrolo[2,3-d]pyrimidine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: HBr; AcOH / CH2Cl2 / 16 h / 20 °C 2.1: KOH; tris[2-(2-methoxyethoxy)ethyl]amine / acetonitrile / 0.25 h / 20 °C 2.2: 61.7 percent / acetonitrile / 0.17 h / 20 °C View Scheme
Multi-step reaction with 2 steps 1.1: hydrogen bromide; acetic acid 2.1: Tris(3,6-dioxaheptyl)amine; potassium hydroxide / acetonitrile / 0.25 h / 20 °C 2.2: 0.17 h / 20 °C View Scheme

: 97614-43-2
1,3,5-tri-O-benzoyl-2-deoxy-2-fluoro-α-D-arabinofuranose

: 2'-deoxy-2'-fluoro-1-β-D-arabinofuranosyl-5-(2-bromovinyl)uracil

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: HBr; acetic acid / 1,2-dichloro-ethane / 0.17 h / 80 °C 2: 1,2-dichloro-ethane / 1 h / 110 °C 3: sodium methoxide / methanol / 0.17 h / 80 °C View Scheme

: 97614-43-2
1,3,5-tri-O-benzoyl-2-deoxy-2-fluoro-α-D-arabinofuranose

: 5-(2-bromo-vinyl)-1-(3-fluoro-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-1H-pyrimidine-2,4-dione

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: HBr; acetic acid / 1,2-dichloro-ethane / 0.17 h / 80 °C 2: 1,2-dichloro-ethane / 1 h / 110 °C 3: sodium methoxide / methanol / 0.17 h / 80 °C View Scheme

: 97614-43-2
1,3,5-tri-O-benzoyl-2-deoxy-2-fluoro-α-D-arabinofuranose

: 1-(3-fluoro-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-5-propyl-1H-pyrimidine-2,4-dione

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: HBr; acetic acid / 1,2-dichloro-ethane / 0.17 h / 80 °C 2: 1,2-dichloro-ethane / 1 h / 110 °C 3: sodium methoxide / methanol / 0.17 h / 80 °C View Scheme

: 97614-43-2
1,3,5-tri-O-benzoyl-2-deoxy-2-fluoro-α-D-arabinofuranose

: 1-(3-fluoro-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-5-trifluoromethyl-1H-pyrimidine-2,4-dione

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: HBr; acetic acid / 1,2-dichloro-ethane / 0.17 h / 80 °C 2: 1,2-dichloro-ethane / 1 h / 110 °C 3: sodium methoxide / methanol / 0.17 h / 80 °C View Scheme

: 97614-43-2
1,3,5-tri-O-benzoyl-2-deoxy-2-fluoro-α-D-arabinofuranose

: C25H20BrFN2O7

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: HBr; acetic acid / 1,2-dichloro-ethane / 0.17 h / 80 °C 2: 1,2-dichloro-ethane / 1 h / 110 °C View Scheme

: 97614-43-2
1,3,5-tri-O-benzoyl-2-deoxy-2-fluoro-α-D-arabinofuranose

: C26H25FN2O7

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: HBr; acetic acid / 1,2-dichloro-ethane / 0.17 h / 80 °C 2: 1,2-dichloro-ethane / 1 h / 110 °C View Scheme

: 97614-43-2
1,3,5-tri-O-benzoyl-2-deoxy-2-fluoro-α-D-arabinofuranose

: C24H18F4N2O7

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: HBr; acetic acid / 1,2-dichloro-ethane / 0.17 h / 80 °C 2: 1,2-dichloro-ethane / 1 h / 110 °C View Scheme

: 97614-43-2
1,3,5-tri-O-benzoyl-2-deoxy-2-fluoro-α-D-arabinofuranose

: 99097-06-0
1-(2-deoxy-2-fluoro-β-D-arabinofuranosyl)-5-propyluracil

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: HBr; acetic acid / 1,2-dichloro-ethane / 0.17 h / 80 °C 2: 1,2-dichloro-ethane / 1 h / 110 °C 3: sodium methoxide / methanol / 0.17 h / 80 °C View Scheme

: 97614-43-2
1,3,5-tri-O-benzoyl-2-deoxy-2-fluoro-α-D-arabinofuranose

: 114652-80-1
1-(2-deoxy-2-fluoro-β-D-arabinofuranosyl)-5-(trifluromethyl)uracil

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: HBr; acetic acid / 1,2-dichloro-ethane / 0.17 h / 80 °C 2: 1,2-dichloro-ethane / 1 h / 110 °C 3: sodium methoxide / methanol / 0.17 h / 80 °C View Scheme

2-Deoxy-2-fluoro-1,3,5-tri-O-benzoyl-D-ribofuranose Chemical Properties

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

2-Deoxy-2-fluoro-1,3,5-tri-O-benzoyl-D-ribofuranose 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

2-Deoxy-2-fluoro-1,3,5-tri-O-benzoyl-D-ribofuranose 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 .

Product Name

2-Deoxy-2-fluoro-1,3,5-tri-O-benzoyl-D-ribofuranose

Synthetic route

2-Deoxy-2-fluoro-1,3,5-tri-O-benzoyl-D-ribofuranose Chemical Properties

2-Deoxy-2-fluoro-1,3,5-tri-O-benzoyl-D-ribofuranose Safety Profile

2-Deoxy-2-fluoro-1,3,5-tri-O-benzoyl-D-ribofuranose Specification

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