97614-43-2

Basic information

• Product Name: 2-Deoxy-2-fluoro-1,3,5-tri-O-benzoyl-D-ribofuranose
• Synonyms: 1,3,5-TRI-O-BENZOYL-2-DEOXY-2-FLUORO-A-D-ARABINOFURANOSE;2-DEOXY-2-FLUORO-1,3,5-TRI-O-BENZOYL-A-D-ARABINOFURANOSE;2-DEOXY-2-FLUORO-1,3,5-TRI-O-BENZOYL-ALPHA-D-ARABINOFURANOSE;2-Deoxy-2-fluoro-1,3,5-tri-O-benzoyl-D-arabinofuranose;2-Deoxy-2-fluoro-α-D-arabinofuranose 1,3,5-Tribenzoate;2-Deoxy-2-Fluoro-1,3,5-Tribenzoate-alpha-D- Arabinofuranose Min98% C3;2-Deoxy-2-fluoro-1,3,5-tri-O-benzoyl-α- D-arabinof;InterMediate of Clofarabine
• CAS NO: 97614-43-2
• Molecular Formula: C26H21FO7
• Molecular Weight: 464.44
• EINECS: 1312995-182-4
• Product Categories: Carbohydrates & Derivatives;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 97614-43-2.mol
• Article Data: 12

Chemical Properties

• Melting Point: 74-77°C
• Boiling Point: 584.1 °C at 760 mmHg
• Flash Point: 295.7 °C
• Appearance: White to Off-white/Powder
• Density: 1.35 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.607
• Storage Temp.: 2-8°C
• Solubility: Soluble in chloroform or dichloromethane
• CAS DataBase Reference: 2-Deoxy-2-fluoro-1,3,5-tri-O-benzoyl-D-ribofuranose(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Deoxy-2-fluoro-1,3,5-tri-O-benzoyl-D-ribofuranose(97614-43-2)
• EPA Substance Registry System: 2-Deoxy-2-fluoro-1,3,5-tri-O-benzoyl-D-ribofuranose(97614-43-2)

Safety Data

• Safety Statements: 24/25
• WGK Germany: 3
• Hazardous Substances Data: 97614-43-2(Hazardous Substances Data)

Usage

Chemical Properties

White Solid

Uses

Different sources of media describe the Uses of 97614-43-2 differently. You can refer to the following data:
1. It is a pharmaceutical intermediate and is used as an OLED materials.
2. Clofarabine intermediate.

InChI:InChI=1/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-/m1/s1

Synthetic route

2-O-<(trifluoromethyl)sulfonyl>-1,3,5-tri-O-benzoyl-α-D-ribofuranose (97614-41-0) → 1,3,5-tri-O-benzoyl-2-deoxy-2-fluoro-α-D-arabinofuranose (97614-43-2)

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;

1,3,5-tri-O-benzoyl-α-D-ribofuranoside (22224-41-5) → 1,3,5-tri-O-benzoyl-2-deoxy-2-fluoro-α-D-arabinofuranose (97614-43-2)

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

2-O-(imidazolylsulfonyl)-1,3,5-tri-O-benzoyl-α-D-ribofuranose (97614-42-1) → 1,3,5-tri-O-benzoyl-2-deoxy-2-fluoro-α-D-arabinofuranose (97614-43-2)

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: Et3N*3HF / ethyl acetate / 20 - 60 °C 2: Et3N*3HF / ethyl acetate / 70 °C View Scheme

2-O-(imidazolylsulfonyl)-1,3,5-tri-O-benzoyl-α-D-ribofuranose (97614-42-1) → 1,3,5-tri-O-benzoyl-2-deoxy-2-fluoro-α-D-arabinofuranose (97614-43-2) + 2-O-(fluorosulfonyl)-1,3,5-tri-O-benzoyl-α-D-ribofuranose (97614-50-1)

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

2-O-(fluorosulfonyl)-1,3,5-tri-O-benzoyl-α-D-ribofuranose (97614-50-1) → 1,3,5-tri-O-benzoyl-2-deoxy-2-fluoro-α-D-arabinofuranose (97614-43-2) + 1,3,5-tri-O-benzoyl-α-D-arabinofuranose

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

2-O-<(trifluoromethyl)sulfonyl>-1,3,5-tri-O-benzoyl-α-D-ribofuranose (97614-41-0) → 1,3,5-tri-O-benzoyl-2-deoxy-2-fluoro-α-D-arabinofuranose (97614-43-2) + 1,3,5-tri-O-benzoyl-α-D-arabinofuranose

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

ethylene glycol (107-21-1) + 2-O-(imidazolylsulfonyl)-1,3,5-tri-O-benzoyl-α-D-ribofuranose (97614-42-1) → β-phenyl hydroxypropionate (38491-60-0) + 1,3,5-tri-O-benzoyl-2-deoxy-2-fluoro-α-D-arabinofuranose (97614-43-2) + C28H26O9 (97614-49-8)

Conditions	Yield
With potassium hydrogen bifluoride; hydrogen fluoride In various solvent(s) at 160℃; for 1h; Product distribution; other reaction conditions;

2-O-(fluorosulfonyl)-1,3,5-tri-O-benzoyl-α-D-ribofuranose (97614-50-1) → 1,3,5-tri-O-benzoyl-2-deoxy-2-fluoro-α-D-arabinofuranose (97614-43-2)

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;

1,3,5-tri-O-benzoyl-2-deoxy-2-fluoro-α-D-arabinofuranose (97614-43-2) → 2-deoxy-2-fluoro-3,5-di-O-benzoyl-α-D-arabinofuranosyl bromide (97614-44-3)

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%

1,3,5-tri-O-benzoyl-2-deoxy-2-fluoro-α-D-arabinofuranose (97614-43-2) → ((2R,3R,4S)-3-(benzoyloxy)-5-bromo-4-fluorotetrahydrofuran-2-yl)methyl benzoate (98855-71-1)

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

dichloromethane (75-09-2) + 1,3,5-tri-O-benzoyl-2-deoxy-2-fluoro-α-D-arabinofuranose (97614-43-2) → ((2R,3R,4S)-3-(benzoyloxy)-5-bromo-4-fluorotetrahydrofuran-2-yl)methyl benzoate (98855-71-1)

Conditions	Yield
With hydrogen bromide; acetic acid	90%

1,3,5-tri-O-benzoyl-2-deoxy-2-fluoro-α-D-arabinofuranose (97614-43-2) → sevoflurane (28523-86-6)

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

octanol (111-87-5) + 1,3,5-tri-O-benzoyl-2-deoxy-2-fluoro-α-D-arabinofuranose (97614-43-2) → octyl 2-deoxy-2-fluoro-3,5-di-O-benzoyl-β-D-arabinofuranoside + octyl 2-deoxy-2-fluoro-3,5-di-O-benzoyl-α-D-arabinofuranoside (1131273-34-1)

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%

1,3,5-tri-O-benzoyl-2-deoxy-2-fluoro-α-D-arabinofuranose (97614-43-2) + 9-Trimethylsilyl-2,6-dichlorpurin (75788-35-1) → C24H17Cl2FN4O5 + C24H17Cl2FN4O5 + ((2R,3R,4S,5R)-3-(benzoyloxy)-5-(2,6-dichloro-9H-purin-9-yl)-4-fluorotetrahydrofuran-2-yl)methyl benzoate (329187-80-6) + C24H17Cl2FN4O5 (329187-81-7)

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

1,3,5-tri-O-benzoyl-2-deoxy-2-fluoro-α-D-arabinofuranose (97614-43-2) + 6-benzoylamino-9-trimethylsilylpurine (60855-35-8) → 9-(2-deoxy-2-fluoro-β-D-arabinofuranosyl)adenine (20187-82-0, 20227-41-2, 64183-27-3, 123334-75-8) + 9-(2-deoxy-2-fluoro-α-D-arabinofuranosyl)adenine (20187-82-0) + 7-(2-deoxy-2-fluoro-α-D-arabinofuranosyl)adenine

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%

1,3,5-tri-O-benzoyl-2-deoxy-2-fluoro-α-D-arabinofuranose (97614-43-2) + 2,4-bis(trimethylsiloxy)-5-methylpyrimidine (7288-28-0) → C23H19FN2O7

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

1,3,5-tri-O-benzoyl-2-deoxy-2-fluoro-α-D-arabinofuranose (97614-43-2) → 4-amino-7-(2-deoxy-2-fluoro-β-D-arabinofuranosyl)-5-fluoro-7H-pyrrolo[2,3-d]pyrimidine (909101-48-0)

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

1,3,5-tri-O-benzoyl-2-deoxy-2-fluoro-α-D-arabinofuranose (97614-43-2) → 7-(2-deoxy-2-fluoro-β-D-arabinofuranosyl)-5-fluoro-4-methoxy-7H-pyrrolo[2,3-d]pyrimidine (909101-50-4)

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

1,3,5-tri-O-benzoyl-2-deoxy-2-fluoro-α-D-arabinofuranose (97614-43-2) → 7-(2-deoxy-2-fluoro-β-D-arabinofuranosyl)-3,7-dihydro-5-fluoro-4H-pyrrolo[2,3-d]pyrimidin-4-one

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

1,3,5-tri-O-benzoyl-2-deoxy-2-fluoro-α-D-arabinofuranose (97614-43-2) → 4-chloro-7-(2-deoxy-3,5-di-O-benzoyl-β-D-arabinofuranosyl)-5-fluoro-7H-pyrrolo[2,3-d]pyrimidine (909101-46-8)

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

1,3,5-tri-O-benzoyl-2-deoxy-2-fluoro-α-D-arabinofuranose (97614-43-2) → 2'-deoxy-2'-fluoro-1-β-D-arabinofuranosyl-5-(2-bromovinyl)uracil

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

1,3,5-tri-O-benzoyl-2-deoxy-2-fluoro-α-D-arabinofuranose (97614-43-2) → 5-(2-bromo-vinyl)-1-(3-fluoro-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-1H-pyrimidine-2,4-dione

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

1,3,5-tri-O-benzoyl-2-deoxy-2-fluoro-α-D-arabinofuranose (97614-43-2) → 1-(3-fluoro-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-5-propyl-1H-pyrimidine-2,4-dione

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

1,3,5-tri-O-benzoyl-2-deoxy-2-fluoro-α-D-arabinofuranose (97614-43-2) → 1-(3-fluoro-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-5-trifluoromethyl-1H-pyrimidine-2,4-dione

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

1,3,5-tri-O-benzoyl-2-deoxy-2-fluoro-α-D-arabinofuranose (97614-43-2) → C25H20BrFN2O7

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

1,3,5-tri-O-benzoyl-2-deoxy-2-fluoro-α-D-arabinofuranose (97614-43-2) → C26H25FN2O7

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

1,3,5-tri-O-benzoyl-2-deoxy-2-fluoro-α-D-arabinofuranose (97614-43-2) → C24H18F4N2O7

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

1,3,5-tri-O-benzoyl-2-deoxy-2-fluoro-α-D-arabinofuranose (97614-43-2) → 1-(2-deoxy-2-fluoro-β-D-arabinofuranosyl)-5-propyluracil (99097-06-0)

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

1,3,5-tri-O-benzoyl-2-deoxy-2-fluoro-α-D-arabinofuranose (97614-43-2) → 1-(2-deoxy-2-fluoro-β-D-arabinofuranosyl)-5-(trifluromethyl)uracil (114652-80-1)

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

Upstream product

• 107-21-1 ethylene glycol 
• 97614-42-1 2-O-(imidazolylsulfonyl)-1,3,5-tri-O-benzoyl-α-D-ribofuranose 
• 97614-50-1 2-O-(fluorosulfonyl)-1,3,5-tri-O-benzoyl-α-D-ribofuranose 
• 97614-41-0 2-O-<(trifluoromethyl)sulfonyl>-1,3,5-tri-O-benzoyl-α-D-ribofuranose 
• 22224-41-5 1,3,5-tri-O-benzoyl-α-D-ribofuranoside 

Downstream Products

• 28523-86-6 sevoflurane 
• 136228-12-1 5-O-Benzoyl-2-deoxy-2-fluoro-1-O-methyl-β-D-arabinofuranose 
• 136228-14-3 5-O-Benzoyl-2-deoxy-2-fluoro-1-O-methyl-3-O-(methylthio)thiocarbonyl-β-D-arabinofuranose 
• 98855-71-1 ((2R,3R,4S)-3-(benzoyloxy)-5-bromo-4-fluorotetrahydrofuran-2-yl)methyl benzoate 
• 1131273-34-1 octyl 2-deoxy-2-fluoro-3,5-di-O-benzoyl-α-D-arabinofuranoside 
• 1338072-67-5 7-(3,5-di-O-benzoyl-2-deoxy-2-fluoro-β-D-arabinofuranosyl)-4-phenyl-7H-pyrrolo[2,3-d]pyrimidine 
• 1338072-69-7 7-(3,5-di-O-benzoyl-2-deoxy-2-fluoro-β-D-arabinofuranosyl)-4-(furan-2-yl)-7H-pyrrolo[2,3-d]pyrimidine 
• 1338072-72-2 7-(3,5-di-O-benzoyl-2-deoxy-2-fluoro-β-D-arabinofuranosyl)-4-(thiophen-2-yl)-7H-pyrrolo[2,3-d]pyrimidine 
• 1338072-75-5 7-(3,5-di-O-benzoyl-2-deoxy-2-fluoro-β-D-arabinofuranosyl)-4-(furan-3-yl)-7H-pyrrolo[2,3-d]pyrimidine 
• 169516-55-6 4-chloro-7-(3',5'-di-O-benzoyl-2'-deoxy-2'-fluoro-β-D-arabinofuranosyl)pyrrolo<2,3-d>pyrimidine 
• 1382358-19-1 1-(2-deoxy-2-fluoro-3,5-di-O-benzoyl-β-D-arabinofuranosyl)-5-iodocytosine 
• 69123-90-6 fiacitabine 
• 1393605-17-8 4-chloro-5-iodo-7-(2-deoxy-2-fluoro-3,5-di-O-benzoyl-β-D-arabinofuranosyl)-7H-pyrrolo[2,3-d]pyrimidine 
• 1393605-19-0 C₁₇H₁₇FN₄O₃ 

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