2,3'-anhydro-N⁴-benzoyl-1-<2-deoxy-5-O-(4-methoxybenzoyl)-β-D-threo-pentofuranosyl>cytosine

Base Information

• Chemical Name: 2,3'-anhydro-N⁴-benzoyl-1-<2-deoxy-5-O-(4-methoxybenzoyl)-β-D-threo-pentofuranosyl>cytosine
• CAS No.: 161664-15-9
• Molecular Formula: C₂₄H₂₁N₃O₆
• Molecular Weight: 447.447
• Mol file: 161664-15-9.mol

Synonyms:

Chemical Property of 2,3'-anhydro-N⁴-benzoyl-1-<2-deoxy-5-O-(4-methoxybenzoyl)-β-D-threo-pentofuranosyl>cytosine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2,3'-anhydro-N⁴-benzoyl-1-<2-deoxy-5-O-(4-methoxybenzoyl)-β-D-threo-pentofuranosyl>cytosine

There total 1 articles about 2,3'-anhydro-N⁴-benzoyl-1-<2-deoxy-5-O-(4-methoxybenzoyl)-β-D-threo-pentofuranosyl>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: 70.0%

4-methoxybenzoic acid (100-09-4) + N4-benzoyl-2'-deoxycytidine (4836-13-9) → 2,3'-anhydro-N4-benzoyl-1-<2-deoxy-5-O-(4-methoxybenzoyl)-β-D-threo-pentofuranosyl>cytosine (161664-15-9)

Guidance literature:

With di-isopropyl azodicarboxylate; triphenylphosphine; In N,N-dimethyl-formamide; for 0.666667h; Ambient temperature;

DOI:10.1002/hlca.19940770402

Reference yield:

2,3'-anhydro-N4-benzoyl-1-<2-deoxy-5-O-(4-methoxybenzoyl)-β-D-threo-pentofuranosyl>cytosine (161664-15-9) → N4-benzoyl-1-<3-O-benzoyl-2-deoxy-5-O-(4,4'-dimethoxytriphenylmethyl)-β-D-threo-pentofuranosyl>cytosine (161664-19-3)

Guidance literature:

Multi-step reaction with 4 steps

1: 89 percent / Dowex 1*2 resin OH^(1-) form / ethanol; H₂O / 20 h / 50 °C

2: 1.) Me₃SiCl, 2.) 25percent aq. NH₃ / 1.) pyridine, 140 min, room temp. then 4.5 h, room temp., 2.) 0 deg C, pyridine, water

3: 85 percent / pyridine / 5 h / Ambient temperature

4: 83 percent / Et₃N / acetonitrile / 6 h / Ambient temperature

With ammonium hydroxide; chloro-trimethyl-silane; Dowex 1*2 resin OH^(1-) form; triethylamine; In pyridine; ethanol; water; acetonitrile;

DOI:10.1002/hlca.19940770402

Reference yield:

2,3'-anhydro-N4-benzoyl-1-<2-deoxy-5-O-(4-methoxybenzoyl)-β-D-threo-pentofuranosyl>cytosine (161664-15-9) → N4-benzoyl-1-<2-deoxy-5-O-(4,4'-dimethoxytriphenylmethyl)-β-D-threo-pentofuranosyl>cytosine 3'-<(2-cyanoethyl) N,N-diisopropylphosphoramidite>

Guidance literature:

Multi-step reaction with 4 steps

1: 89 percent / Dowex 1*2 resin OH^(1-) form / ethanol; H₂O / 20 h / 50 °C

2: 1.) Me₃SiCl, 2.) 25percent aq. NH₃ / 1.) pyridine, 140 min, room temp. then 4.5 h, room temp., 2.) 0 deg C, pyridine, water

3: 85 percent / pyridine / 5 h / Ambient temperature

4: 17 percent / N-ethyldiisopropylamine / CH₂Cl₂ / 0.5 h / Ambient temperature

With ammonium hydroxide; chloro-trimethyl-silane; Dowex 1*2 resin OH^(1-) form; N-ethyl-N,N-diisopropylamine; In pyridine; ethanol; dichloromethane; water;

DOI:10.1002/hlca.19940770402

upstream raw materials:

4-methoxybenzoic acid

N₄-benzoyl-2'-deoxycytidine

Downstream raw materials:

1-<2-deoxy-5-O-(4,4'-dimethoxytriphenylmethyl)-β-D-threo-pentofuranosyl>-4-(2-methylpropanoyl)cytosine

N⁴-benzoyl-1-(2-deoxy-5-O-(4,4'-dimethoxytriphenylmethyl)-β-D-threo-pentofuranosyl)cytosine

N⁴-benzoyl-1-<3-O-benzoyl-2-deoxy-5-O-(4,4'-dimethoxytriphenylmethyl)-β-D-threo-pentofuranosyl>cytosine

N⁴-benzoyl-1-(2-deoxy-β-D-threo-pentofuranosyl)cytosine

Refernces