1-[2,3-dideoxy-3,3-difluoro-4-thio-5-O-toluoyl-β-L-ribofuranosyl]-N₄-benzoyl-5-fluorocytosine

Base Information

• Chemical Name: 1-[2,3-dideoxy-3,3-difluoro-4-thio-5-O-toluoyl-β-L-ribofuranosyl]-N₄-benzoyl-5-fluorocytosine
• CAS No.: 676598-32-6
• Molecular Formula: C₂₄H₂₀F₃N₃O₄S
• Molecular Weight: 503.502

Synonyms:1-[2,3-dideoxy-3,3-difluoro-4-thio-5-O-toluoyl-β-L-ribofuranosyl]-N₄-benzoyl-5-fluorocytosine

Chemical Property of 1-[2,3-dideoxy-3,3-difluoro-4-thio-5-O-toluoyl-β-L-ribofuranosyl]-N₄-benzoyl-5-fluorocytosine

Chemical Property:

Purity/Quality:

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Technology Process of 1-[2,3-dideoxy-3,3-difluoro-4-thio-5-O-toluoyl-β-L-ribofuranosyl]-N₄-benzoyl-5-fluorocytosine

There total 7 articles about 1-[2,3-dideoxy-3,3-difluoro-4-thio-5-O-toluoyl-β-L-ribofuranosyl]-N₄-benzoyl-5-fluorocytosine 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: 33.0%

N-benzoyl-5-fluorocytosine (10357-07-0) + 1-O-acetyl-2,3-dideoxy-3,3-difluoro-4-thio-5-O-toluoyl-L-furanose (676598-27-9) → 1-[2,3-dideoxy-3,3-difluoro-4-thio-5-O-toluoyl-α-L-ribofuranosyl]-N4-benzoyl-5-fluorocytosine (676598-33-7) + 1-[2,3-dideoxy-3,3-difluoro-4-thio-5-O-toluoyl-β-L-ribofuranosyl]-N4-benzoyl-5-fluorocytosine (676598-32-6)

Guidance literature:

N-benzoyl-5-fluorocytosine; 1-O-acetyl-2,3-dideoxy-3,3-difluoro-4-thio-5-O-toluoyl-L-furanose; With N,O-bis-(trimethylsilyl)-acetamide; In acetonitrile; at 50 - 60 ℃; for 2h;

With trimethylsilyl trifluoromethanesulfonate; In acetonitrile; for 3h; Heating;

DOI:10.1021/jm0303148

Reference yield:

methyl 2-deoxy-5-O-(4-methylbenzoyl)-D-erythro-pentofuranoside (676598-19-9) → 1-[2,3-dideoxy-3,3-difluoro-4-thio-5-O-toluoyl-β-L-ribofuranosyl]-N4-benzoyl-5-fluorocytosine (676598-32-6)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 73 percent / pyridinium dichromate; molecular sieves 4 Angstroem / CH₂Cl₂ / 4 h / 20 °C

2.1: 55 percent / (diethylamino)sulfur trifluoride / CH₂Cl₂ / 24 h / 20 °C

3.1: 94 percent / boron trifluoride etherate / CH₂Cl₂ / 2 h / 40 °C

4.1: 2,6-lutidine / CH₂Cl₂ / 0.92 h / -10 - 0 °C

5.1: 27.6 g / BaCO₃; n-TBAI / 3 h / 50 - 60 °C

6.1: 72 percent / acetic acid; mercuric acetate / 24 h / 20 °C

7.1: N,O-bis(trimethylsilyl)acetamide / acetonitrile / 2 h / 50 - 60 °C

7.2: 32 percent / TMSOTf / acetonitrile / 3 h / Heating

With 2,6-dimethylpyridine; dipyridinium dichromate; N,O-bis-(trimethylsilyl)-acetamide; diethylamino-sulfur trifluoride; 4 A molecular sieve; boron trifluoride diethyl etherate; mercury(II) diacetate; tetra-(n-butyl)ammonium iodide; acetic acid; barium carbonate; In dichloromethane; acetonitrile;

DOI:10.1021/jm0303148

Reference yield:

methyl-2-deoxy-5-O-toluoyl-D-furan-3-ulose (676598-21-3) → 1-[2,3-dideoxy-3,3-difluoro-4-thio-5-O-toluoyl-β-L-ribofuranosyl]-N4-benzoyl-5-fluorocytosine (676598-32-6)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 55 percent / (diethylamino)sulfur trifluoride / CH₂Cl₂ / 24 h / 20 °C

2.1: 94 percent / boron trifluoride etherate / CH₂Cl₂ / 2 h / 40 °C

3.1: 2,6-lutidine / CH₂Cl₂ / 0.92 h / -10 - 0 °C

4.1: 27.6 g / BaCO₃; n-TBAI / 3 h / 50 - 60 °C

5.1: 72 percent / acetic acid; mercuric acetate / 24 h / 20 °C

6.1: N,O-bis(trimethylsilyl)acetamide / acetonitrile / 2 h / 50 - 60 °C

6.2: 32 percent / TMSOTf / acetonitrile / 3 h / Heating

With 2,6-dimethylpyridine; N,O-bis-(trimethylsilyl)-acetamide; diethylamino-sulfur trifluoride; boron trifluoride diethyl etherate; mercury(II) diacetate; tetra-(n-butyl)ammonium iodide; acetic acid; barium carbonate; In dichloromethane; acetonitrile;

DOI:10.1021/jm0303148

upstream raw materials:

N-benzoyl-5-fluorocytosine

1-O-acetyl-2,3-dideoxy-3,3-difluoro-4-thio-5-O-toluoyl-L-furanose

methyl 2-deoxy-5-O-(4-methylbenzoyl)-D-erythro-pentofuranoside

methyl-2-deoxy-5-O-toluoyl-D-furan-3-ulose

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