N⁴-benzoyl-1-[3-C-(benzyloxymethyl)-2,3-dideoxy-3-C-methyl-α-D-glycero-tetrofuranosyl]-5-fluorocytosine

Base Information

• Chemical Name: N⁴-benzoyl-1-[3-C-(benzyloxymethyl)-2,3-dideoxy-3-C-methyl-α-D-glycero-tetrofuranosyl]-5-fluorocytosine
• CAS No.: 301826-17-5
• Molecular Formula: C₂₄H₂₄FN₃O₄
• Molecular Weight: 437.471

Synonyms:N⁴-benzoyl-1-[3-C-(benzyloxymethyl)-2,3-dideoxy-3-C-methyl-α-D-glycero-tetrofuranosyl]-5-fluorocytosine

Chemical Property of N⁴-benzoyl-1-[3-C-(benzyloxymethyl)-2,3-dideoxy-3-C-methyl-α-D-glycero-tetrofuranosyl]-5-fluorocytosine

Chemical Property:

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Technology Process of N⁴-benzoyl-1-[3-C-(benzyloxymethyl)-2,3-dideoxy-3-C-methyl-α-D-glycero-tetrofuranosyl]-5-fluorocytosine

There total 3 articles about N⁴-benzoyl-1-[3-C-(benzyloxymethyl)-2,3-dideoxy-3-C-methyl-α-D-glycero-tetrofuranosyl]-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: 30.0%

1-O-acetyl-3-C-(benzyloxymethyl)-2,3-dideoxy-3-C-methyl-D-glycero-tetrofuranose (301826-40-4) + N-(5-fluoro-2-oxo-1-trimethylsilanyl-1,2-dihydro-pyrimidin-4-yl)-benzamide → N4-benzoyl-1-[3-C-(benzyloxymethyl)-2,3-dideoxy-3-C-methyl-β-D-glycero-tetrofuranosyl]-5-fluorocytosine (301826-16-4) + N4-benzoyl-1-[3-C-(benzyloxymethyl)-2,3-dideoxy-3-C-methyl-α-D-glycero-tetrofuranosyl]-5-fluorocytosine (301826-17-5)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; 1,2-dichloro-ethane; at 20 ℃; for 2h;

DOI:10.1016/S0008-6215(00)00005-7

Reference yield:

3-C-(benzyloxymethyl)-2,3-dideoxy-3-C-methyl-D-glycero-tetrofuranose (220569-97-1) → N4-benzoyl-1-[3-C-(benzyloxymethyl)-2,3-dideoxy-3-C-methyl-α-D-glycero-tetrofuranosyl]-5-fluorocytosine (301826-17-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 89.2 percent / pyridine

2: 24 percent / Me₃SiOTf / CH₂Cl₂; 1,2-dichloro-ethane / 2 h / 20 °C

With trimethylsilyl trifluoromethanesulfonate; pyridine; In dichloromethane; 1,2-dichloro-ethane; 1: Acetylation / 2: Alkylation;

DOI:10.1016/S0008-6215(00)00005-7

Reference yield:

ethyl (R)-3-benzyloxymethyl-3-methyl-4-oxobutyrate (220569-96-0) → N4-benzoyl-1-[3-C-(benzyloxymethyl)-2,3-dideoxy-3-C-methyl-α-D-glycero-tetrofuranosyl]-5-fluorocytosine (301826-17-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 67.2 percent / DIBAL-H / toluene / 3 h / -78 °C

2: 89.2 percent / pyridine

3: 24 percent / Me₃SiOTf / CH₂Cl₂; 1,2-dichloro-ethane / 2 h / 20 °C

With trimethylsilyl trifluoromethanesulfonate; diisobutylaluminium hydride; pyridine; In dichloromethane; 1,2-dichloro-ethane; toluene; 1: Reduction / 2: Acetylation / 3: Alkylation;

DOI:10.1016/S0008-6215(00)00005-7

upstream raw materials:

1-O-acetyl-3-C-(benzyloxymethyl)-2,3-dideoxy-3-C-methyl-D-glycero-tetrofuranose

3-C-(benzyloxymethyl)-2,3-dideoxy-3-C-methyl-D-glycero-tetrofuranose

ethyl (R)-3-benzyloxymethyl-3-methyl-4-oxobutyrate

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