N⁴-benzoyl-1-(2,3-di-O-benzoyl-β-D-arabinofuranosyl)cytosine 5'-[(prop-3-yl hepta-O-acetyl-β-lactoside)-1-yl] phosphate

Base Information

• Chemical Name: N⁴-benzoyl-1-(2,3-di-O-benzoyl-β-D-arabinofuranosyl)cytosine 5'-[(prop-3-yl hepta-O-acetyl-β-lactoside)-1-yl] phosphate
• CAS No.: 196083-30-4
• Molecular Formula: C₅₉H₆₆N₃O₂₉P
• Molecular Weight: 1312.15

Synonyms:N⁴-benzoyl-1-(2,3-di-O-benzoyl-β-D-arabinofuranosyl)cytosine 5'-[(prop-3-yl hepta-O-acetyl-β-lactoside)-1-yl] phosphate

Chemical Property of N⁴-benzoyl-1-(2,3-di-O-benzoyl-β-D-arabinofuranosyl)cytosine 5'-[(prop-3-yl hepta-O-acetyl-β-lactoside)-1-yl] phosphate

Chemical Property:

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Technology Process of N⁴-benzoyl-1-(2,3-di-O-benzoyl-β-D-arabinofuranosyl)cytosine 5'-[(prop-3-yl hepta-O-acetyl-β-lactoside)-1-yl] phosphate

There total 3 articles about N⁴-benzoyl-1-(2,3-di-O-benzoyl-β-D-arabinofuranosyl)cytosine 5'-[(prop-3-yl hepta-O-acetyl-β-lactoside)-1-yl] phosphate 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: 60.0%

N4-benzoyl-1-(2,3-di-O-benzoyl-β-D-arabinofuranosyl)cytosine 5'-[(prop-3-yl hepta-O-acetyl-β-lactoside)-1-yl] phosphonate (196083-28-0) → N4-benzoyl-1-(2,3-di-O-benzoyl-β-D-arabinofuranosyl)cytosine 5'-[(prop-3-yl hepta-O-acetyl-β-lactoside)-1-yl] phosphate (196083-30-4)

Guidance literature:

With iodine; bis-(trimethylsilyl)acetamide; triethylamine; In tetrahydrofuran; for 4h; Ambient temperature;

DOI:10.1016/S0008-6215(97)00137-7

Reference yield:

Acetic acid (2R,3R,4S,5R,6R)-3-acetoxy-6-acetoxymethyl-2-(3-hydroxy-propoxy)-5-((2S,3R,4S,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-4-yl ester (196083-23-5) → N4-benzoyl-1-(2,3-di-O-benzoyl-β-D-arabinofuranosyl)cytosine 5'-[(prop-3-yl hepta-O-acetyl-β-lactoside)-1-yl] phosphate (196083-30-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 93 percent / pivaloyl chloride, Py / acetonitrile / 0.08 h / Ambient temperature

2: 60 percent / Et₃N, bis(trimethylsilyl)acetamide, I₂ / tetrahydrofuran / 4 h / Ambient temperature

With pyridine; iodine; pivaloyl chloride; bis-(trimethylsilyl)acetamide; triethylamine; In tetrahydrofuran; acetonitrile;

DOI:10.1016/S0008-6215(97)00137-7

Reference yield:

C30H26N3O10P*C6H15N → N4-benzoyl-1-(2,3-di-O-benzoyl-β-D-arabinofuranosyl)cytosine 5'-[(prop-3-yl hepta-O-acetyl-β-lactoside)-1-yl] phosphate (196083-30-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 93 percent / pivaloyl chloride, Py / acetonitrile / 0.08 h / Ambient temperature

2: 60 percent / Et₃N, bis(trimethylsilyl)acetamide, I₂ / tetrahydrofuran / 4 h / Ambient temperature

With pyridine; iodine; pivaloyl chloride; bis-(trimethylsilyl)acetamide; triethylamine; In tetrahydrofuran; acetonitrile;

DOI:10.1016/S0008-6215(97)00137-7

upstream raw materials:

N⁴-benzoyl-1-(2,3-di-O-benzoyl-β-D-arabinofuranosyl)cytosine 5'-[(prop-3-yl hepta-O-acetyl-β-lactoside)-1-yl] phosphonate

Acetic acid (2R,3R,4S,5R,6R)-3-acetoxy-6-acetoxymethyl-2-(3-hydroxy-propoxy)-5-((2S,3R,4S,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-4-yl ester

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