(E)-N⁴-benzoyl-1-<<1-<(tert-butyldimethylsilyl)oxy>-4-(diisopropoxyphosphoryl)but-3-en-2-yl>oxy>cytosine

Base Information

• Chemical Name: (E)-N⁴-benzoyl-1-<<1-<(tert-butyldimethylsilyl)oxy>-4-(diisopropoxyphosphoryl)but-3-en-2-yl>oxy>cytosine
• CAS No.: 148120-86-9
• Molecular Formula: C₂₇H₄₂N₃O₇PSi
• Molecular Weight: 579.706

Synonyms:(E)-N⁴-benzoyl-1-<<1-<(tert-butyldimethylsilyl)oxy>-4-(diisopropoxyphosphoryl)but-3-en-2-yl>oxy>cytosine

Chemical Property of (E)-N⁴-benzoyl-1-<<1-<(tert-butyldimethylsilyl)oxy>-4-(diisopropoxyphosphoryl)but-3-en-2-yl>oxy>cytosine

Chemical Property:

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Technology Process of (E)-N⁴-benzoyl-1-<<1-<(tert-butyldimethylsilyl)oxy>-4-(diisopropoxyphosphoryl)but-3-en-2-yl>oxy>cytosine

There total 5 articles about (E)-N⁴-benzoyl-1-<<1-<(tert-butyldimethylsilyl)oxy>-4-(diisopropoxyphosphoryl)but-3-en-2-yl>oxy>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: 91.0%

4-benzamido-1-hydroxyuracil (139177-39-2) + diisopropyl <(E)-4-<(tert-butyldimethylsilyl)oxy>-3-hydroxybut-1-enyl>phosphonate (148154-16-9) → (E)-N4-benzoyl-1-<<1-<(tert-butyldimethylsilyl)oxy>-4-(diisopropoxyphosphoryl)but-3-en-2-yl>oxy>cytosine (148120-86-9)

Guidance literature:

With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; for 16h; Ambient temperature;

DOI:10.1021/jm00062a006

Reference yield:

Tetraisopropyl methylenediphosphonate (1660-95-3) → (E)-N4-benzoyl-1-<<1-<(tert-butyldimethylsilyl)oxy>-4-(diisopropoxyphosphoryl)but-3-en-2-yl>oxy>cytosine (148120-86-9)

Guidance literature:

Multi-step reaction with 4 steps

1: 1.) n-butyllithium / 1.) n-heptane, n-hexane, -78 deg C, 0.5 h, 2.) n-heptane, n-hexane, 100 deg C, 1 h

2: 54 percent / acetic acid / H₂O; tetrahydrofuran / 16 h / 80 °C

3: 68 percent / triethylamine, 4-(dimethylamino)pyridine / CH₂Cl₂ / 66 h / Ambient temperature

4: 91 percent / PPh₃, DEAD / tetrahydrofuran / 16 h / Ambient temperature

With dmap; n-butyllithium; acetic acid; triethylamine; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; dichloromethane; water;

DOI:10.1021/jm00062a006

Reference yield:

tert-butyldimethylsilyl chloride (18162-48-6) → (E)-N4-benzoyl-1-<<1-<(tert-butyldimethylsilyl)oxy>-4-(diisopropoxyphosphoryl)but-3-en-2-yl>oxy>cytosine (148120-86-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 68 percent / triethylamine, 4-(dimethylamino)pyridine / CH₂Cl₂ / 66 h / Ambient temperature

2: 91 percent / PPh₃, DEAD / tetrahydrofuran / 16 h / Ambient temperature

With dmap; triethylamine; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; dichloromethane;

DOI:10.1021/jm00062a006

upstream raw materials:

4-benzamido-1-hydroxyuracil

diisopropyl <(E)-4-<(tert-butyldimethylsilyl)oxy>-3-hydroxybut-1-enyl>phosphonate

Tetraisopropyl methylenediphosphonate

tert-butyldimethylsilyl chloride

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