1-(2-deoxy-4-thio-β-L-ribofuranosyl)-N4-benzoyl-cytosine

Base Information

• Chemical Name: 1-(2-deoxy-4-thio-β-L-ribofuranosyl)-N4-benzoyl-cytosine
• CAS No.: 219661-98-0
• Molecular Formula: C₁₆H₁₇N₃O₄S
• Molecular Weight: 347.395
• Mol file: 219661-98-0.mol

Synonyms:1-(2-deoxy-4-thio-β-L-ribofuranosyl)-N4-benzoyl-cytosine

Chemical Property of 1-(2-deoxy-4-thio-β-L-ribofuranosyl)-N4-benzoyl-cytosine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-(2-deoxy-4-thio-β-L-ribofuranosyl)-N4-benzoyl-cytosine

There total 11 articles about 1-(2-deoxy-4-thio-β-L-ribofuranosyl)-N4-benzoyl-cytosine 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:

1-(2-deoxy-3,5-di-O-benzyl-4-thio-β-L-ribofuranosyl)-N4-benzoyl-cytosine (219661-94-6) → 1-(2-deoxy-4-thio-β-L-ribofuranosyl)-N4-benzoyl-cytosine (219661-98-0)

Guidance literature:

With boron trichloride; In dichloromethane; at -78 ℃; for 6h;

DOI:10.1080/07328319808004318

Reference yield:

(3R,4R,5R)-4-(benzyloxy)-5-(benzyloxymethyl)-2-methoxytetrahydrofuran-3-ol (102339-30-0) → 1-(2-deoxy-4-thio-β-L-ribofuranosyl)-N4-benzoyl-cytosine (219661-98-0)

Guidance literature:

Multi-step reaction with 8 steps

1: 88 percent / 1,2-dichloro-ethane / 3 h / Heating

2: 80 percent / (Me₃Si)3SiH, AIBN / toluene / 2 h / Heating

3: 66 percent / BF₃, Et₂O

4: pyridine

5: 89 percent / BaCO₃, NBu₄I

6: 75 percent / acetic acid / 1 h / Ambient temperature

7: 45 percent / TMSOTf, BSA / acetonitrile / 6 h / Heating

8: BCl₃ / CH₂Cl₂ / 6 h / -78 °C

With benzenesulfonamide; diethyl ether; 2,2'-azobis(isobutyronitrile); trimethylsilyl trifluoromethanesulfonate; tris-(trimethylsilyl)silane; boron trifluoride; boron trichloride; tetra-(n-butyl)ammonium iodide; barium carbonate; In pyridine; dichloromethane; acetic acid; 1,2-dichloro-ethane; toluene; acetonitrile;

DOI:10.1080/07328319808004318

Reference yield:

3,5-di-O-benzyl-1,2-O-isopropylidene-α-D-xylofuranose (41341-99-5) → 1-(2-deoxy-4-thio-β-L-ribofuranosyl)-N4-benzoyl-cytosine (219661-98-0)

Guidance literature:

Multi-step reaction with 10 steps

1: aq. CF₃COOH / 3 h / 0 °C

2: 90 percent / conc. H₂SO₄ / 24 h / 0 °C

3: 88 percent / 1,2-dichloro-ethane / 3 h / Heating

4: 80 percent / (Me₃Si)3SiH, AIBN / toluene / 2 h / Heating

5: 66 percent / BF₃, Et₂O

6: pyridine

7: 89 percent / BaCO₃, NBu₄I

8: 75 percent / acetic acid / 1 h / Ambient temperature

9: 45 percent / TMSOTf, BSA / acetonitrile / 6 h / Heating

10: BCl₃ / CH₂Cl₂ / 6 h / -78 °C

With benzenesulfonamide; diethyl ether; 2,2'-azobis(isobutyronitrile); trimethylsilyl trifluoromethanesulfonate; tris-(trimethylsilyl)silane; sulfuric acid; boron trifluoride; boron trichloride; tetra-(n-butyl)ammonium iodide; barium carbonate; trifluoroacetic acid; In pyridine; dichloromethane; acetic acid; 1,2-dichloro-ethane; toluene; acetonitrile;

DOI:10.1080/07328319808004318

upstream raw materials:

1-(2-deoxy-3,5-di-O-benzyl-4-thio-β-L-ribofuranosyl)-N4-benzoyl-cytosine

(3R,4R,5R)-4-(benzyloxy)-5-(benzyloxymethyl)-2-methoxytetrahydrofuran-3-ol

3,5-di-O-benzyl-1,2-O-isopropylidene-α-D-xylofuranose

(2R,3R)-3-(benzyloxy)-2-(benzyloxymethyl)-5-methoxytetrahydrofuran

Downstream raw materials:

1-(5-O-tert-butyldimethylsilyl-2-deoxy-4-thio-β-L-ribofuranosyl)-N4-benzoyl-cytosine

Refernces