78842-13-4

Basic information

• Product Name: 2'-Deoxy-2'-fluoroguanosine
• Synonyms: 2'-deoxy-2'-fluoroguanosine;2'-FdG;2'-Fluoro -2'-deoxyguanosine;2'-F-2'-dG;Guanosine,2'-deoxy-2'-fluoro-
• CAS NO: 78842-13-4
• Molecular Formula: C₁₀H₁₂FN₅O₄
• Molecular Weight: 285.2317832
• EINECS: 1806241-263-5
• Mol File: 78842-13-4.mol
• Article Data: 28

Chemical Properties

• Melting Point: 262-264 °C(Solv: water (7732-18-5))
• Appearance: White to Off-white/Powder
• Density: 2.17±0.1 g/cm3(Predicted)
• Storage Temp.: 2-8°C(protect from light)
• PKA: 9?+-.0.20(Predicted)
• CAS DataBase Reference: 2'-Deoxy-2'-fluoroguanosine(CAS DataBase Reference)
• NIST Chemistry Reference: 2'-Deoxy-2'-fluoroguanosine(78842-13-4)
• EPA Substance Registry System: 2'-Deoxy-2'-fluoroguanosine(78842-13-4)

Safety Data

• Hazardous Substances Data: 78842-13-4(Hazardous Substances Data)

Usage

Uses

2''-Deoxy-2''-fluoroguanosine, can be used as powerful tool for structural manipulation of G-quadruplexes. It is also a influenza viral polymerase inhibitor like Ribavirin (R414475), used as a antiviral drug against avian (H5N1) influenza virus.

Synthetic route

2,6-diamino-9-(2-deoxy-2-fluoro-β-D-ribofuranosyl)-9H-purine (134444-47-6) → 2'-deoxy-2'-fluoroguanosine (78842-13-4)

Conditions	Yield
In water for 20h; Ambient temperature; adenosine deaminase;	83%
With ADase Substitution;

2’-fluoro-N2-isobutyryl-2’-deoxyguanosine (80681-25-0) → 2'-deoxy-2'-fluoroguanosine (78842-13-4)

Conditions	Yield
With ammonia at 20℃; for 16h;	80%
With ammonium hydroxide at 55℃; for 24h; Yield given;

N2-isobutyryl-3',5'-di-O-tetrahydrofuranyl-2'-fluoro-2'-deoxyguanosine → 2'-chloro-2'-deoxyguanosine (80980-30-9) + 2'-deoxy-2'-fluoroguanosine (78842-13-4)

Conditions	Yield
With ammonium hydroxide In pyridine at 50℃; for 3h;	A n/a B 44%

C24H20FN5O6 → 2'-deoxy-2'-fluoroguanosine (78842-13-4)

Conditions	Yield
With ammonia In methanol at 0℃; for 24h;	13%

N2-isobutyryl-3'-O,5'-O-bis(tetrahydrofuranyl)-2'-deoxy-2'-fluoroguanosine (78842-12-3) → 2'-deoxy-2'-fluoroguanosine (78842-13-4)

Conditions	Yield
With ammonium hydroxide; acetic acid 1.) pyridine, 50 deg C, 3 h; 2.) H2O, 30 deg C, 2 h; Yield given. Multistep reaction;

1-O-acetyl-3,5-di-O-benzoyl-2-deoxy-2-fluoro-β-D-ribofuranoside (149623-91-6) + trimethylsilylated N2-palmitoylguanine → 2'-deoxy-2'-fluoroguanosine (78842-13-4) + 2'-deoxy-2'-fluoroguanosine + 7-(2-deoxy-2-fluoro-β-D-ribofuranosyl)guanine

Conditions	Yield
Multistep reaction;

2'-deoxy-2'-fluorocytidine (10212-20-1) → 2'-deoxy-2'-fluoroguanosine (78842-13-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: E. coli BMT-4D/1A 2: ADase View Scheme

2,6-diaminopurine (1904-98-9) → 2'-deoxy-2'-fluoroguanosine (78842-13-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: E. coli BMT-4D/1A 2: ADase View Scheme
Multi-step reaction with 2 steps 1: E. coli BMT-4D/1A 2: ADase View Scheme

2'-deoxy-2'-fluorouridine (56287-17-3, 69123-94-0, 784-71-4) → 2'-deoxy-2'-fluoroguanosine (78842-13-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: E. coli BMT-4D/1A 2: ADase View Scheme

9-β-D-arabinofuranosylguanine (38819-10-2) → 2'-deoxy-2'-fluoroguanosine (78842-13-4)

Conditions	Yield
Multi-step reaction with 6 steps 1: 1.) TMSCl, pyridine, 3.) NH4OH 2: TsOH / dioxane 3: DMAP / CH2Cl2 4: TBAF / tetrahydrofuran 5: Dowex-50 / methanol 6: NH4OH / 24 h / 55 °C View Scheme
Multi-step reaction with 10 steps 1: 1.) TMSCl, pyridine, 3.) NH4OH 2: pyridine 4: HF*pyridine 5: TsOH / dioxane 6: NaOH / pyridine; methanol 7: DMAP / CH2Cl2 8: TBAF / tetrahydrofuran 9: Dowex-50 / methanol 10: NH4OH / 24 h / 55 °C View Scheme

2,6-diamino-9-(2,3,5-tri-O-benzyl-β-D-arabinofuranosyl)purine (24880-52-2) → 2'-deoxy-2'-fluoroguanosine (78842-13-4)

Conditions	Yield
Multi-step reaction with 8 steps 1: 1.) BCl3, 2.) NaOH / 1.) CH2Cl2 2: adenosine deaminase / 72 h / 37 °C / phosphate buffer, pH 7-7.5 3: 1.) TMSCl, pyridine, 3.) NH4OH 4: TsOH / dioxane 5: DMAP / CH2Cl2 6: TBAF / tetrahydrofuran 7: Dowex-50 / methanol 8: NH4OH / 24 h / 55 °C View Scheme
Multi-step reaction with 12 steps 1: 1.) BCl3, 2.) NaOH / 1.) CH2Cl2 2: adenosine deaminase / 72 h / 37 °C / phosphate buffer, pH 7-7.5 3: 1.) TMSCl, pyridine, 3.) NH4OH 4: pyridine 6: HF*pyridine 7: TsOH / dioxane 8: NaOH / pyridine; methanol 9: DMAP / CH2Cl2 10: TBAF / tetrahydrofuran 11: Dowex-50 / methanol 12: NH4OH / 24 h / 55 °C View Scheme

N2-isobutyryl-9-(3,5-di-O-tetrahydropyran-2-yl-β-D-arabinofuranosyl)guanine (146954-68-9) → 2'-deoxy-2'-fluoroguanosine (78842-13-4)

Conditions	Yield
Multi-step reaction with 4 steps 1: DMAP / CH2Cl2 2: TBAF / tetrahydrofuran 3: Dowex-50 / methanol 4: NH4OH / 24 h / 55 °C View Scheme
Multi-step reaction with 4 steps 1: pyridine, (N,N-dimethylamino)pyrydine / CH2Cl2 / 1 h / 5 °C 2: tertbutylammonium fluoride / tetrahydrofuran / 5 h / 5 °C 3: 41 percent / Dowex 50W x 2-100 / methanol / 1 h / 23 °C 4: 80 percent / sat. NH3 in MeOH / 16 h / 20 °C View Scheme

Acetic acid (2R,3S,4R,5R)-4-hydroxy-5-hydroxymethyl-2-(2-isobutyrylamino-6-oxo-1,6-dihydro-purin-9-yl)-tetrahydro-furan-3-yl ester (160684-49-1) → 2'-deoxy-2'-fluoroguanosine (78842-13-4)

Conditions	Yield
Multi-step reaction with 6 steps 1: TsOH / dioxane 2: NaOH / pyridine; methanol 3: DMAP / CH2Cl2 4: TBAF / tetrahydrofuran 5: Dowex-50 / methanol 6: NH4OH / 24 h / 55 °C View Scheme

N2-isobutyryl-9-[3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-β-D-arabinofuranosyl]guanine (160684-47-9) → 2'-deoxy-2'-fluoroguanosine (78842-13-4)

Conditions	Yield
Multi-step reaction with 8 steps 2: HF*pyridine 3: TsOH / dioxane 4: NaOH / pyridine; methanol 5: DMAP / CH2Cl2 6: TBAF / tetrahydrofuran 7: Dowex-50 / methanol 8: NH4OH / 24 h / 55 °C View Scheme

Acetic acid (2R,3S,4R,5R)-2-(2-isobutyrylamino-6-oxo-1,6-dihydro-purin-9-yl)-4-(tetrahydro-pyran-2-yloxy)-5-(tetrahydro-pyran-2-yloxymethyl)-tetrahydro-furan-3-yl ester → 2'-deoxy-2'-fluoroguanosine (78842-13-4)

Conditions	Yield
Multi-step reaction with 5 steps 1: NaOH / pyridine; methanol 2: DMAP / CH2Cl2 3: TBAF / tetrahydrofuran 4: Dowex-50 / methanol 5: NH4OH / 24 h / 55 °C View Scheme

Acetic acid (2R,3S,3aR,9aR)-2-(2-isobutyrylamino-6-oxo-1,6-dihydro-purin-9-yl)-5,5,7,7-tetraisopropyl-tetrahydro-1,4,6,8-tetraoxa-5,7-disila-cyclopentacycloocten-3-yl ester (160684-48-0) → 2'-deoxy-2'-fluoroguanosine (78842-13-4)

Conditions	Yield
Multi-step reaction with 7 steps 1: HF*pyridine 2: TsOH / dioxane 3: NaOH / pyridine; methanol 4: DMAP / CH2Cl2 5: TBAF / tetrahydrofuran 6: Dowex-50 / methanol 7: NH4OH / 24 h / 55 °C View Scheme

2,6-diamino-9-(β-D-arabinofuranosyl)-purine (34079-68-0) → 2'-deoxy-2'-fluoroguanosine (78842-13-4)

Conditions	Yield
Multi-step reaction with 7 steps 1: adenosine deaminase / 72 h / 37 °C / phosphate buffer, pH 7-7.5 2: 1.) TMSCl, pyridine, 3.) NH4OH 3: TsOH / dioxane 4: DMAP / CH2Cl2 5: TBAF / tetrahydrofuran 6: Dowex-50 / methanol 7: NH4OH / 24 h / 55 °C View Scheme
Multi-step reaction with 11 steps 1: adenosine deaminase / 72 h / 37 °C / phosphate buffer, pH 7-7.5 2: 1.) TMSCl, pyridine, 3.) NH4OH 3: pyridine 5: HF*pyridine 6: TsOH / dioxane 7: NaOH / pyridine; methanol 8: DMAP / CH2Cl2 9: TBAF / tetrahydrofuran 10: Dowex-50 / methanol 11: NH4OH / 24 h / 55 °C View Scheme

1-O-acetyl-3,5-di-O-benzoyl-2-deoxy-2-fluoro-β-D-ribofuranoside (149623-91-6) → 2'-deoxy-2'-fluoroguanosine (78842-13-4)

Conditions

Yield

Multi-step reaction with 5 steps 1: 23 percent / p-TsOH / 0.83 h / 160 °C / 25 Torr 2: 75 percent / NaN3 / ethanol; H2O / 1.) reflux, 1 h, 2.) room temperature, 20 h 3: 94 percent / H2 / Pd on carbon / ethanol; N,N-dimethyl-acetamide / 20 h / Ambient temperature 4: 79 percent / MeONa / methanol / 1 h / Ambient temperature 5: 83 percent / H2O / 20 h / Ambient temperature; adenosine deaminase View Scheme

2,6-diamino-9-(3,5-di-O-benzoyl-2-deoxy-2-fluoro-β-D-ribofuranosyl)purine (156357-14-1) → 2'-deoxy-2'-fluoroguanosine (78842-13-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: 79 percent / MeONa / methanol / 1 h / Ambient temperature 2: 83 percent / H2O / 20 h / Ambient temperature; adenosine deaminase View Scheme

2,6-diazido-9-(3,5-di-O-benzoyl-2-deoxy-2-fluoro-β-D-ribofuranosyl)purine (156357-13-0) → 2'-deoxy-2'-fluoroguanosine (78842-13-4)

Conditions	Yield
Multi-step reaction with 3 steps 1: 94 percent / H2 / Pd on carbon / ethanol; N,N-dimethyl-acetamide / 20 h / Ambient temperature 2: 79 percent / MeONa / methanol / 1 h / Ambient temperature 3: 83 percent / H2O / 20 h / Ambient temperature; adenosine deaminase View Scheme

3,5-di-O-benzoyl-2-deoxy-2-fluoro-D-ribofuranosyl bromide → 2'-deoxy-2'-fluoroguanosine (78842-13-4)

Conditions

Yield

Multi-step reaction with 5 steps 1: 59 percent / mercuric cyanide / various solvent(s) / 24 h / Ambient temperature 2: 75 percent / NaN3 / ethanol; H2O / 1.) reflux, 1 h, 2.) room temperature, 20 h 3: 94 percent / H2 / Pd on carbon / ethanol; N,N-dimethyl-acetamide / 20 h / Ambient temperature 4: 79 percent / MeONa / methanol / 1 h / Ambient temperature 5: 83 percent / H2O / 20 h / Ambient temperature; adenosine deaminase View Scheme

2,6-dichloro-9-(3,5-di-O-benzoyl-2-deoxy-2-fluoro-β-D-ribofuranosyl)purine (156357-16-3) → 2'-deoxy-2'-fluoroguanosine (78842-13-4)

Conditions	Yield
Multi-step reaction with 4 steps 1: 75 percent / NaN3 / ethanol; H2O / 1.) reflux, 1 h, 2.) room temperature, 20 h 2: 94 percent / H2 / Pd on carbon / ethanol; N,N-dimethyl-acetamide / 20 h / Ambient temperature 3: 79 percent / MeONa / methanol / 1 h / Ambient temperature 4: 83 percent / H2O / 20 h / Ambient temperature; adenosine deaminase View Scheme

2,6-dichloro-7H-purine (5451-40-1) → 2'-deoxy-2'-fluoroguanosine (78842-13-4)

Conditions

Yield

Multi-step reaction with 5 steps 1: 59 percent / mercuric cyanide / various solvent(s) / 24 h / Ambient temperature 2: 75 percent / NaN3 / ethanol; H2O / 1.) reflux, 1 h, 2.) room temperature, 20 h 3: 94 percent / H2 / Pd on carbon / ethanol; N,N-dimethyl-acetamide / 20 h / Ambient temperature 4: 79 percent / MeONa / methanol / 1 h / Ambient temperature 5: 83 percent / H2O / 20 h / Ambient temperature; adenosine deaminase View Scheme

3',5'-O-1,1,3,3-tetraisopropyldisiloxan-1,3-diyl-guanosine (69304-44-5) → 2'-deoxy-2'-fluoroguanosine (78842-13-4)

Conditions

Yield

Multi-step reaction with 10 steps 1: DMSO, acetic anhydride 2: NaBH4 / 1.5 h / 0 °C 3: 80 percent / pyridine / 20 h / 60 °C 4: 80 percent / n-Bu4NF 5: 82 percent / p-toluenesulfonic acid / dioxane / 2 h / 23 °C 6: 78 percent / NaOH / acetonitrile; methanol; H2O 7: pyridine, (N,N-dimethylamino)pyrydine / CH2Cl2 / 1 h / 5 °C 8: tertbutylammonium fluoride / tetrahydrofuran / 5 h / 5 °C 9: 41 percent / Dowex 50W x 2-100 / methanol / 1 h / 23 °C 10: 80 percent / sat. NH3 in MeOH / 16 h / 20 °C View Scheme

2-amino-9-((6aR,8R,9aR)-2,2,4,4-tetraisopropyl-9-oxotetrahydro-6H-furo[3,2-f][1,3,5,2,4]trioxadisilocin-8-yl)-1H-purin-6(9H)-one (129835-15-0) → 2'-deoxy-2'-fluoroguanosine (78842-13-4)

Conditions

Yield

Multi-step reaction with 9 steps 1: NaBH4 / 1.5 h / 0 °C 2: 80 percent / pyridine / 20 h / 60 °C 3: 80 percent / n-Bu4NF 4: 82 percent / p-toluenesulfonic acid / dioxane / 2 h / 23 °C 5: 78 percent / NaOH / acetonitrile; methanol; H2O 6: pyridine, (N,N-dimethylamino)pyrydine / CH2Cl2 / 1 h / 5 °C 7: tertbutylammonium fluoride / tetrahydrofuran / 5 h / 5 °C 8: 41 percent / Dowex 50W x 2-100 / methanol / 1 h / 23 °C 9: 80 percent / sat. NH3 in MeOH / 16 h / 20 °C View Scheme

N2-isobutyryl-9-(2-O-isobutyryl-β-D-arabinofuranosyl)guanine (146954-66-7) → 2'-deoxy-2'-fluoroguanosine (78842-13-4)

Conditions	Yield
Multi-step reaction with 6 steps 1: 82 percent / p-toluenesulfonic acid / dioxane / 2 h / 23 °C 2: 78 percent / NaOH / acetonitrile; methanol; H2O 3: pyridine, (N,N-dimethylamino)pyrydine / CH2Cl2 / 1 h / 5 °C 4: tertbutylammonium fluoride / tetrahydrofuran / 5 h / 5 °C 5: 41 percent / Dowex 50W x 2-100 / methanol / 1 h / 23 °C 6: 80 percent / sat. NH3 in MeOH / 16 h / 20 °C View Scheme

Isobutyric acid (2R,3S,4R,5R)-2-(2-isobutyrylamino-6-oxo-1,6-dihydro-purin-9-yl)-4-(tetrahydro-pyran-2-yloxy)-5-(tetrahydro-pyran-2-yloxymethyl)-tetrahydro-furan-3-yl ester (146954-67-8) → 2'-deoxy-2'-fluoroguanosine (78842-13-4)

Conditions	Yield
Multi-step reaction with 5 steps 1: 78 percent / NaOH / acetonitrile; methanol; H2O 2: pyridine, (N,N-dimethylamino)pyrydine / CH2Cl2 / 1 h / 5 °C 3: tertbutylammonium fluoride / tetrahydrofuran / 5 h / 5 °C 4: 41 percent / Dowex 50W x 2-100 / methanol / 1 h / 23 °C 5: 80 percent / sat. NH3 in MeOH / 16 h / 20 °C View Scheme

tert-butyldimethylsilyl chloride (18162-48-6) + 2'-deoxy-2'-fluoroguanosine (78842-13-4) → C22H40FN5O4Si2

Conditions	Yield
With pyridine; 1H-imidazole at 25℃; for 15h; Time;	99%
With pyridine; 1H-imidazole at 25℃; for 15h;	99%
With 1H-imidazole In pyridine at 25℃; for 15h;	99%
With pyridine; 1H-imidazole at 25℃; for 15h;	83%

2'-deoxy-2'-fluoroguanosine (78842-13-4) → 8-bromo-2'-deoxy-2'-fluoroguanosine (847649-66-5)

Conditions	Yield
With bromine In water	94%
With N-Bromosuccinimide In water at 0℃; for 2.33333h; Inert atmosphere;	47%

acetic anhydride (108-24-7) + 2'-deoxy-2'-fluoroguanosine (78842-13-4) + mono-4-methoxytrityl chloride (14470-28-1) → C34H32FN5O7 (1445392-68-6)

Conditions	Yield
Stage #1: acetic anhydride; 2'-deoxy-2'-fluoroguanosine With pyridine at 0 - 25℃; for 10h; Stage #2: mono-4-methoxytrityl chloride With silver nitrate at 0 - 25℃; for 10h;	93%

2'-deoxy-2'-fluoroguanosine (78842-13-4) + mono-4-methoxytrityl chloride (14470-28-1) → C30H28FN5O5 (1365256-12-7)

Conditions	Yield
Stage #1: 2'-deoxy-2'-fluoroguanosine With pyridine; acetic anhydride at 0 - 20℃; for 10h; Stage #2: mono-4-methoxytrityl chloride With silver nitrate at 20℃; for 10h; Stage #3: With ammonia In methanol at 20℃; for 14h;	87.5%
Stage #1: 2'-deoxy-2'-fluoroguanosine With acetic anhydride In pyridine at 0 - 20℃; for 10h; Stage #2: mono-4-methoxytrityl chloride With silver nitrate In pyridine at 20℃; for 10h; Stage #3: With ammonia In methanol at 20℃; for 14h;	9.2 g

acetic anhydride (108-24-7) + 2'-deoxy-2'-fluoroguanosine (78842-13-4) → 2’-fluoro-2’-deoxyguanosine-3’,5’-O-diacetate (134444-75-0)

Conditions	Yield
With pyridine In N,N-dimethyl-formamide at 23℃; for 12h; Inert atmosphere;	79%
With dmap; triethylamine In acetonitrile at 20℃; for 2h;	78%
With pyridine at 20℃;	5 g

tert-butyldimethylsilyl chloride (18162-48-6) + 2'-deoxy-2'-fluoroguanosine (78842-13-4) → C16H26FN5O4Si (1445381-77-0)

Conditions	Yield
Stage #1: tert-butyldimethylsilyl chloride; 2'-deoxy-2'-fluoroguanosine With pyridine; 1H-imidazole at 25℃; for 15h; Stage #2: With acetic acid In tetrahydrofuran; water at 80℃; for 13h;	60.9%
Stage #1: tert-butyldimethylsilyl chloride; 2'-deoxy-2'-fluoroguanosine With 1H-imidazole In pyridine at 25℃; for 15h; Stage #2: With acetic acid In tetrahydrofuran; water at 80℃; for 13h;	31.2 g

2'-deoxy-2'-fluoroguanosine (78842-13-4) + tert-butylchlorodiphenylsilane (58479-61-1) → C26H30FN5O4Si

Conditions	Yield
With 1H-imidazole In N,N-dimethyl-formamide at 20℃; Inert atmosphere;	45%

2'-deoxy-2'-fluoroguanosine (78842-13-4) → C10H13N5O7FP

Conditions	Yield
With phosphorous acid trimethyl ester; trichlorophosphate at 0℃; for 2h;

Upstream product

• 80681-25-0 2’-fluoro-N2-isobutyryl-2’-deoxyguanosine 
• 75173-96-5 tetraisopropyldisiloxanyl (TPDS) protected 9-beta-D-arabinofuranosylguanine 
• 38659-96-0 8,2'-O-cycloguanosine 
• 78842-14-5 N-{9-[(2R,3S,4S,5R)-3-Hydroxy-4-(tetrahydro-furan-2-yloxy)-5-(tetrahydro-furan-2-yloxymethyl)-tetrahydro-furan-2-yl]-8-mercapto-6-oxo-6,9-dihydro-1H-purin-2-yl}-isobutyramide 
• 78857-74-6 N²-isobutyryl-3'-O,5'-O-(tetrahydrofuranyl)-8,2'-anhydro-8-oxy-9-β-D-arabinofuranosylguanine 
• 78842-11-2 N²-isobutyryl-3'-O,5'-O-bis(tetrahydrofuranyl)-9β-D-arabinofuranosylguanine 
• 78842-10-1 N²-isobutyryl-8,2'-anhydro-8-oxy-9β-D-arabinofuranosylguanine 
• 129835-17-2 9-[3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-β-D-arabinofuranosyl]guanine 
• 146954-65-6 N²-isobutyryl-9-(2-O-isobutyryl-3,5-O-(tetraisopropyldisiloxanylene)-β-D-arabinofuranosyl)guanine 
• 146954-67-8 Isobutyric acid (2R,3S,4R,5R)-2-(2-isobutyrylamino-6-oxo-1,6-dihydro-purin-9-yl)-4-(tetrahydro-pyran-2-yloxy)-5-(tetrahydro-pyran-2-yloxymethyl)-tetrahydro-furan-3-yl ester 
• 146954-66-7 N²-isobutyryl-9-(2-O-isobutyryl-β-D-arabinofuranosyl)guanine 
• 129835-15-0 2-amino-9-((6aR,8R,9aR)-2,2,4,4-tetraisopropyl-9-oxotetrahydro-6H-furo[3,2-f][1,3,5,2,4]trioxadisilocin-8-yl)-1H-purin-6(9H)-one 
• 69304-44-5 3',5'-O-1,1,3,3-tetraisopropyldisiloxan-1,3-diyl-guanosine 
• 5451-40-1 2,6-dichloro-7H-purine 

Downstream Products

• 80681-25-0 2’-fluoro-N2-isobutyryl-2’-deoxyguanosine 
• 144089-96-3 N-(9-((2R,3R,4R,5R)-5-((bis(4-methoxyphenyl)(phenyl)methoxy)methyl)-3-fluoro-4-hydroxytetrahydrofuran-2-yl)-6-oxo-6,9-dihydro-1H-purin-2-yl)isobutyramide 
• 1431557-59-3 2’-deoxy-2’-fluoro-6-chloroguanosine-5’-O-phenyl(ethoxy-L-alaninyl)phosphate 
• 1431557-58-2 2’-deoxy-2’-fluoro-6-chloroguanosine-5’-O-phenyl(benzoxy-L-alaninyl)phosphate 
• 1431557-55-9 2’-deoxy-2’-fluoro-6-chloroguanosine-5’-O-naphthyl(benzoxy-L-alaninyl)phosphate 
• 1431557-70-8 6-O-ethyl-2’-fluoro-2’-deoxyguanosine-5’-O-phenyl(ethoxy-L-alaninyl)phosphate 
• 1431557-52-6 6-O-ethyl-2’-fluoro-2’-deoxyguanosine-5’-O-phenyl(benzoxy-L-alaninyl)phosphate 
• 1431558-38-1 6-O-ethyl-2’-fluoro-2’-deoxyguanosine-5’-O-naphthyl(benzoxy-L-alaninyl)phosphate 

Relevant articles and documents

Synthesis and conformational analysis of 1′- and 3′-substituted 2-deoxy-2-fluoro-D-ribofuranosyl nucleosides

Convergent syntheses of the 9-(3-X-2,3-dideoxy-2-fluoro-β-D- ribofuranosyl)adenines 5 (X = N3) and 7 (X = NH2), as well as of their respective α-anomers 6 and 8, are described, using methyl 2-azido-5-O-benzoyl-2,3-dideoxy-2-fluoro-β-D-ribofuranoside (4) as glycosylating agent. Methyl 5-O-benzoyl-2,3-dideoxy-2,3-difluoro-β-D- ribofuranoside (12) was prepared starting from two precursors, and coupled with silylated N6-benzoyladenine to afford, after deprotection, 2′,3′-dideoxy-2′,3′-difluoroadenosine (13). Condensation of 1-O-acetyl-3,5-di-O-benzoyl-2-deoxy-2-fluoro-β-D-ribofuranose (14) with silylated N2-palmitoylguanine gave, after chromatographic separation and deacylation, the N7-β-anomer 17 as the main product, along with 2′-deoxy-2′-fluoroguanosine (15) and its N9-α- anomer 16 in a ratio of ca. 42:24:10. An in-depth conformational analysis of a number of 2,3-dideoxy-2-fluoro-3-X-D-ribofuranosides (X = F, N3, NH2, H) as well as of purine and pyrimidine 2-deoxy-2-fluoro-D- ribofuranosyl nucleosides was performed using the PSEUROT (version 6.3) software in combination with NMR studies.

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