2'-Deoxy-2'-fluoro-D-guanosine

Base Information

• Chemical Name: 2'-Deoxy-2'-fluoro-D-guanosine
• CAS No.: 125291-17-0
• Molecular Formula: C₁₀H₁₂FN₅O₃
• Molecular Weight: 269.235
• Mol file: 125291-17-0.mol

Synonyms:2'-Deoxy-2'-fluoro-D-guanosine;2'-fluoro-2',3'-dideoxyguanosine

Chemical Property of 2'-Deoxy-2'-fluoro-D-guanosine

Chemical Property:

• Boiling Point: 633.5 °C at 760 mmHg
• Flash Point: 336.9 °C
• PSA: 139.28000
• Density: 2.01 g/cm³
• LogP: -1.12830

Purity/Quality:

98%Min ^*data from raw suppliers

2'-DEOXY-2'-FLUORO-D-GUANOSINE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 2'-Deoxy-2'-fluoro-D-guanosine

There total 13 articles about 2'-Deoxy-2'-fluoro-D-guanosine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 61.0%

N2-acetyl-9-(5-O-benzoyl-2,3-dideoxy-3-fluoro-β-D-xylofuranosyl)guanine (125291-16-9) → 9-(2,3-dideoxy-3-fluoro-β-D-xylofuranosyl)guanine (125291-17-0)

Guidance literature:

With ammonia; In methanol;

DOI:10.1016/S0040-4039(00)99193-7

Reference yield:

1,2-isopropylidene-α-D-ribofuranose (37077-81-9) → 9-(2,3-dideoxy-3-fluoro-β-D-xylofuranosyl)guanine (125291-17-0)

Guidance literature:

Multi-step reaction with 8 steps

1: pyridine / 1 h / Ambient temperature

2: pyridine, 80percent aq. hydrazine / 60 h / Ambient temperature

3: 82 percent / 4-(dimethylamino)pyridine, diethylaminosulfur trifluoride / CH₂Cl₂ / 18 h / -10 - 20 °C

4: 47 percent / CH₃COOH, H₂SO₄

5: 1.) bis(trimethylsilyl)acetamide, 2.) trimethylsilyl triflate, 3.) 80percent aq. NH₂NH₂

6: 4-(dimethylamino)pyridine / acetonitrile / Ambient temperature

7: tributyltin hydride, α,α'-azobisisobutyronitrile / toluene / 2 h / 80 °C

8: 61 percent / NH₃ / methanol / 36 h / Ambient temperature

With pyridine; dmap; diethylamino-sulfur trifluoride; trimethylsilyl trifluoromethanesulfonate; sulfuric acid; azobisisobutyronitrile; ammonia; tri-n-butyl-tin hydride; hydrazine hydrate; acetic acid; bis-(trimethylsilyl)acetamide; In methanol; dichloromethane; toluene; acetonitrile;

DOI:10.1016/0008-6215(93)84056-C

Reference yield:

((3aR,5R,65,6aR)-6-hydroxy-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)methyl benzoate (6612-91-5) → 9-(2,3-dideoxy-3-fluoro-β-D-xylofuranosyl)guanine (125291-17-0)

Guidance literature:

Multi-step reaction with 6 steps

1: 82 percent / 4-(dimethylamino)pyridine, diethylaminosulfur trifluoride / CH₂Cl₂ / 18 h / -10 - 20 °C

2: 47 percent / CH₃COOH, H₂SO₄

3: 1.) bis(trimethylsilyl)acetamide, 2.) trimethylsilyl triflate, 3.) 80percent aq. NH₂NH₂

4: 4-(dimethylamino)pyridine / acetonitrile / Ambient temperature

5: tributyltin hydride, α,α'-azobisisobutyronitrile / toluene / 2 h / 80 °C

6: 61 percent / NH₃ / methanol / 36 h / Ambient temperature

With dmap; diethylamino-sulfur trifluoride; trimethylsilyl trifluoromethanesulfonate; sulfuric acid; azobisisobutyronitrile; ammonia; tri-n-butyl-tin hydride; hydrazine hydrate; acetic acid; bis-(trimethylsilyl)acetamide; In methanol; dichloromethane; toluene; acetonitrile;

DOI:10.1016/0008-6215(93)84056-C

upstream raw materials:

N2-acetyl-9-(5-O-benzoyl-2,3-dideoxy-3-fluoro-β-D-xylofuranosyl)guanine

1,2-isopropylidene-α-D-ribofuranose

((3aR,5R,65,6aR)-6-hydroxy-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)methyl benzoate

5-O-benzoyl-1,2-O-isopropylidene-α-D-ribofuranos-3-ulose