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9-(2-Deoxy-2-fluoroarabinofuranosyl)guanine
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Name

9-(2-Deoxy-2-fluoroarabinofuranosyl)guanine

 EINECS N/A
CAS No. 103884-98-6 Density 2.17 g/cm3
PSA 139.28000 LogP -1.12830
Solubility N/A Melting Point 275-279 °C
Formula C10H12FN5O4 Boiling Point 726.1 °C at 760 mmHg
Molecular Weight 285.235 Flash Point 392.9 °C
Transport Information N/A Appearance N/A
Safety Risk Codes N/A
Molecular Structure Molecular Structure of 103884-98-6 (9-(2-Deoxy-2-fluoroarabinofuranosyl)guanine) Hazard Symbols N/A
Synonyms

2-amino-9-(2-deoxy-2-fluoro-D-arabinofuranosyl)-3,9-dihydro-6H-purin-6-one;6H-purin-6-one, 2-amino-9-(2-deoxy-2-fluoro-D-arabinofuranosyl)-1,9-dihydro-;9-(2-deoxy-2-fluoroarabinofuranosyl)guanine;9-(2-Deoxy-2-fluoro-β-D-arabinofuranosyl)guanine;

Article Data 12

9-(2-Deoxy-2-fluoroarabinofuranosyl)guanine Synthetic route

103884-97-5

9-(2’-deoxy-2’-fluoro-β-D-arabinofuranos-1’-yl)-2-amino-6-aminopurine

103884-98-6

9-(2-deoxy-2-fluoro-β-D-arabinofuranosyl)-guanine

Conditions
ConditionsYield
With hydrogenchloride; Tris buffer; adenosine deaminase In water at 20℃; for 1.5h; pH=7.0; Acidic aqueous solution; Enzymatic reaction;100%
With adenosine deaminase type II at 20℃; for 16h;100%
With potassium dihydrogenphosphate; water; calf intestine adenosine deaminase at 40℃; for 2h; pH=7;87%

3',5'-Di-O-trityl-F-ara-G

103884-98-6

9-(2-deoxy-2-fluoro-β-D-arabinofuranosyl)-guanine

Conditions
ConditionsYield
With trifluoroacetic acid In chloroform for 3h; Ambient temperature;91%
144924-88-9

9-(2'-deoxy-2'-fluoro-β-D-arabinofuranos-1'-yl)-2-amino-6-chloropurine

103884-98-6

9-(2-deoxy-2-fluoro-β-D-arabinofuranosyl)-guanine

Conditions
ConditionsYield
With adenosine deaminase from calf intestinal mucosa In aq. phosphate buffer at 25℃; for 19h; pH=7.4; Enzymatic reaction;87%
118373-61-8

2-amino-6-chloro-9-(3',5'-di-O-benzoyl-2'-deoxy-2'-fluoro-β-D-arabinofuranosyl)-9H-purine

103884-98-6

9-(2-deoxy-2-fluoro-β-D-arabinofuranosyl)-guanine

Conditions
ConditionsYield
With sodium methylate; 2-hydroxyethanethiol In methanol for 5h; Reflux;72%
With sodium hydroxide In 1,4-dioxane at 100℃; for 1h;20%
With sodium hydroxide In water
Multi-step reaction with 2 steps
1: ammonia / methanol / 15 h / 20 °C
2: adenosine deaminase from calf intestinal mucosa / aq. phosphate buffer / 19 h / 25 °C / pH 7.4 / Enzymatic reaction
View Scheme
134222-04-1

N2-acetyl-9-(3,5-di-O-benzoyl-2-deoxy-2-fluoro-β-D-arabinofuranosyl)guanine

103884-98-6

9-(2-deoxy-2-fluoro-β-D-arabinofuranosyl)-guanine

Conditions
ConditionsYield
With ammonia In methanol at 20℃; for 48h;70%
109303-94-8

9-(3-O-acetyl-5-O-benzoyl-2-deoxy-2-fluoro-β-D-arabinofuranosyl)-2-acetamido-6-chloropurine

103884-98-6

9-(2-deoxy-2-fluoro-β-D-arabinofuranosyl)-guanine

Conditions
ConditionsYield
With sodium methylate; 2-hydroxyethanethiol In methanol for 3h; Heating;67%

C24H18ClFN4O6

103884-98-6

9-(2-deoxy-2-fluoro-β-D-arabinofuranosyl)-guanine

Conditions
ConditionsYield
With ammonia In methanol at 150℃; for 6h;67%
97614-44-3

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

103884-98-6

9-(2-deoxy-2-fluoro-β-D-arabinofuranosyl)-guanine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 52 percent / CCl4 / 72 h / 77 °C
2: 67 percent / ammonia / methanol / 6 h / 150 °C
View Scheme
Multi-step reaction with 2 steps
1: 27 percent
2: sodium hydroxide / H2O
View Scheme
Multi-step reaction with 3 steps
1: 1.) Hg(CN)2 / 1.) C6H6, reflux, 30 min, 2.) reflux, 3.4 h
2: 1 M Bu4NF / CH2Cl2; tetrahydrofuran / 0.25 h
3: 20 percent / 0.5 N aq. NaOH / dioxane / 1 h / 100 °C
View Scheme

2-chloro-6,9-bis(trimethylsilyl)-9H-purine

103884-98-6

9-(2-deoxy-2-fluoro-β-D-arabinofuranosyl)-guanine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 52 percent / CCl4 / 72 h / 77 °C
2: 67 percent / ammonia / methanol / 6 h / 150 °C
View Scheme
97614-43-2

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

103884-98-6

9-(2-deoxy-2-fluoro-β-D-arabinofuranosyl)-guanine

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: 35 percent / TMSOTf / acetonitrile / 0.33 h / Heating
2.1: LiN3 / ethanol / 2 h / Heating
2.2: benzoyl chloride / pyridine / 18 h / 20 °C
3.1: SnCl2 / CH2Cl2; methanol
4.1: 0.47 g / NH3 / methanol / 24 h / 20 °C
5.1: 0.45 g / adenosine deaminase E.C. 3.5.4.4 a / H2O / 20 °C
View Scheme
Multi-step reaction with 3 steps
1.1: zinc dibromide; trimethylsilyl bromide / dichloromethane / 20.17 h / 0 - 20 °C / Inert atmosphere
2.1: potassium tert-butylate / 1,2-dimethoxyethane / 0.67 h / 20 °C
2.2: 18 h / 20 °C / Inert atmosphere
3.1: 2-hydroxyethanethiol; sodium methylate / methanol / 5 h / Reflux
View Scheme
Multi-step reaction with 4 steps
1.1: zinc dibromide; trimethylsilyl bromide / dichloromethane / 20.17 h / 0 - 20 °C / Inert atmosphere
2.1: potassium tert-butylate / 1,2-dimethoxyethane / 0.67 h / 20 °C
2.2: 18 h / 20 °C / Inert atmosphere
3.1: acetic anhydride; acetic acid / 2.5 h / 120 - 125 °C
4.1: ammonia / methanol / 48 h / 20 °C
View Scheme
Multi-step reaction with 4 steps
1.1: zinc dibromide; trimethylsilyl bromide / dichloromethane / 20.17 h / 0 - 20 °C / Inert atmosphere
2.1: potassium tert-butylate / 1,2-dimethoxyethane / 0.67 h / 20 °C
2.2: 18 h / 20 °C / Inert atmosphere
3.1: ammonia / methanol / 15 h / 20 °C
4.1: adenosine deaminase from calf intestinal mucosa / aq. phosphate buffer / 19 h / 25 °C / pH 7.4 / Enzymatic reaction
View Scheme

9-(2-Deoxy-2-fluoroarabinofuranosyl)guanine Specification

The 9-(2-Deoxy-2-fluoroarabinofuranosyl)guanine, with the cas registry number 103884-98-6, has the systematic name and IUPAC name of 2-amino-9-(2-deoxy-2-fluoro-D-arabinofuranosyl)-3,9-dihydro-6H-purin-6-one. And the molecular formula of the chemical is C10H12FN5O4.

The characteristics of this chemical are as followings: (1)ACD/LogP: -0.53; (2)# of Rule of 5 Violations: 1; (3)ACD/LogD (pH 5.5): -0.53; (4)ACD/LogD (pH 7.4): -0.53; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 12.23; (8)ACD/KOC (pH 7.4): 12.26; (9)#H bond acceptors: 9; (10)#H bond donors: 5; (11)#Freely Rotating Bonds: 4; (12)Polar Surface Area: 81.42 Å2; (13)Index of Refraction: 1.876; (14)Molar Refractivity: 59.82 cm3; (15)Molar Volume: 131 cm3; (16)Polarizability: 23.71×10-24cm3; (17)Surface Tension: 98.5 dyne/cm; (18)Density: 2.17 g/cm3; (19)Flash Point: 392.9 °C; (20)Enthalpy of Vaporization: 111.3 kJ/mol; (21)Boiling Point: 726.1 °C at 760 mmHg; (22)Vapour Pressure: 3.94E-22 mmHg at 25°C.

Addtionally, the following datas could be converted into the molecular structure:
(1)SMILES: O=C3/N=C(/N)Nc1c3ncn1C2O[C@@H]([C@@H](O)[C@@H]2F)CO
(2)InChI: InChI=1/C10H12FN5O4/c11-4-6(18)3(1-17)20-9(4)16-2-13-5-7(16)14-10(12)15-8(5)19/h2-4,6,9,17-18H,1H2,(H3,12,14,15,19)/t3-,4+,6-,9?/m1/s1
(3)InChIKey: UXUZARPLRQRNNX-VPRFCXCPBI

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