N⁴-benzoyl-2'-deoxy-5-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxymethyl)cytidine

Base Information

• Chemical Name: N⁴-benzoyl-2'-deoxy-5-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxymethyl)cytidine
• CAS No.: 354581-68-3
• Molecular Formula: C₃₁H₃₇N₃O₁₅
• Molecular Weight: 691.646

Synonyms:N⁴-benzoyl-2'-deoxy-5-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxymethyl)cytidine

Chemical Property of N⁴-benzoyl-2'-deoxy-5-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxymethyl)cytidine

Chemical Property:

Purity/Quality:

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Technology Process of N⁴-benzoyl-2'-deoxy-5-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxymethyl)cytidine

There total 5 articles about N⁴-benzoyl-2'-deoxy-5-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxymethyl)cytidine 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: 76.0%

N4-benzoyl-3',5'-bis(O-tert-butyldimethylsilyl)-2'-deoxy-5-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxymethyl)cytidine (354581-67-2) → N4-benzoyl-2'-deoxy-5-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxymethyl)cytidine (354581-68-3)

Guidance literature:

With triethylamine tris(hydrogen fluoride); In pyridine;

Reference yield:

5-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)oxymethyl-3',5'-di-O-tert-butyldimethylsilyl-N3-pivaloyloxymethyl-2'-deoxyuridine (244631-64-9) → N4-benzoyl-2'-deoxy-5-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxymethyl)cytidine (354581-68-3)

Guidance literature:

Multi-step reaction with 5 steps

1.1: tBuOK / methanol / 16 h / 60 °C

1.2: 89 percent / pyridine / 1 h

2.1: 86 percent / Et₃N; POCl₃ / acetonitrile

3.1: aq. NH₄OH / dioxane / 1 h

4.1: 0.25 g / pyridine

5.1: 76 percent / Et₃N*3HF / pyridine

With pyridine; ammonium hydroxide; potassium tert-butylate; triethylamine tris(hydrogen fluoride); triethylamine; trichlorophosphate; In 1,4-dioxane; pyridine; methanol; acetonitrile;

Reference yield:

3',5'-bis(O-tert-butyl-dimethylsilyl)-2'-deoxy-5-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)oxymethyluridine (354581-65-0) → N4-benzoyl-2'-deoxy-5-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxymethyl)cytidine (354581-68-3)

Guidance literature:

Multi-step reaction with 4 steps

1: 86 percent / Et₃N; POCl₃ / acetonitrile

2: aq. NH₄OH / dioxane / 1 h

3: 0.25 g / pyridine

4: 76 percent / Et₃N*3HF / pyridine

With pyridine; ammonium hydroxide; triethylamine tris(hydrogen fluoride); triethylamine; trichlorophosphate; In 1,4-dioxane; pyridine; acetonitrile;

upstream raw materials:

N⁴-benzoyl-3',5'-bis(O-tert-butyldimethylsilyl)-2'-deoxy-5-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxymethyl)cytidine

5-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)oxymethyl-3',5'-di-O-tert-butyldimethylsilyl-N³-pivaloyloxymethyl-2'-deoxyuridine

3',5'-bis(O-tert-butyl-dimethylsilyl)-2'-deoxy-5-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)oxymethyluridine

3',5'-bis(O-tert-butyldimethylsilyl)-2'-deoxy-5-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxymethyl)-4-(N¹-1,2,4-triazolyl)uridine

Downstream raw materials:

N⁴-benzoyl-2'-deoxy-5'-O-(4,4'-dimethoxytrityl)-5-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxymethyl)cytidine

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