N⁴-benzoyl-1-[3-C-(benzyloxymethyl)-2,3-dideoxy-3-C-methyl-β-D-glycero-tetrafuranosyl]cytosine

Base Information

• Chemical Name: N⁴-benzoyl-1-[3-C-(benzyloxymethyl)-2,3-dideoxy-3-C-methyl-β-D-glycero-tetrafuranosyl]cytosine
• CAS No.: 301826-41-5
• Molecular Formula: C₂₄H₂₅N₃O₄
• Molecular Weight: 419.48

Synonyms:N⁴-benzoyl-1-[3-C-(benzyloxymethyl)-2,3-dideoxy-3-C-methyl-β-D-glycero-tetrafuranosyl]cytosine

Chemical Property of N⁴-benzoyl-1-[3-C-(benzyloxymethyl)-2,3-dideoxy-3-C-methyl-β-D-glycero-tetrafuranosyl]cytosine

Chemical Property:

Purity/Quality:

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Technology Process of N⁴-benzoyl-1-[3-C-(benzyloxymethyl)-2,3-dideoxy-3-C-methyl-β-D-glycero-tetrafuranosyl]cytosine

There total 4 articles about N⁴-benzoyl-1-[3-C-(benzyloxymethyl)-2,3-dideoxy-3-C-methyl-β-D-glycero-tetrafuranosyl]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:

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-β-D-glycero-tetrafuranosyl]cytosine (301826-41-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 89.2 percent / pyridine

2: 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-β-D-glycero-tetrafuranosyl]cytosine (301826-41-5)

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: 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

Reference yield:

N-(2-((1-trimethylsilyl)oxy)pyrimidin-4-yl)benzamide (238096-55-4) + 1-O-acetyl-3-C-(benzyloxymethyl)-2,3-dideoxy-3-C-methyl-D-glycero-tetrofuranose (301826-40-4) → N4-benzoyl-1-[3-C-(benzyloxymethyl)-2,3-dideoxy-3-C-methyl-β-D-glycero-tetrafuranosyl]cytosine (301826-41-5) + N4-benzoyl-1-[3-C-(benzyloxymethyl)-2,3-dideoxy-3-C-methyl-α-D-glycero-tetrofuranosyl]cytosine (301826-42-6)

Guidance literature:

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

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

upstream raw materials:

N-(2-((1-trimethylsilyl)oxy)pyrimidin-4-yl)benzamide

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

4-N-benzoylcytosine

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

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