(5'S)-N⁴-benzoyl-5'-C-butyl-3'-O-[(tert-butyl)dimethylsilyl]-2'-deoxy-5-methyl-5'-O-(9-phenyl-9H-xanthen-9-yl)cytidine

Base Information

• Chemical Name: (5'S)-N⁴-benzoyl-5'-C-butyl-3'-O-[(tert-butyl)dimethylsilyl]-2'-deoxy-5-methyl-5'-O-(9-phenyl-9H-xanthen-9-yl)cytidine
• CAS No.: 331822-67-4
• Molecular Formula: C₄₆H₅₃N₃O₆Si
• Molecular Weight: 772.029

Synonyms:(5'S)-N⁴-benzoyl-5'-C-butyl-3'-O-[(tert-butyl)dimethylsilyl]-2'-deoxy-5-methyl-5'-O-(9-phenyl-9H-xanthen-9-yl)cytidine

Chemical Property of (5'S)-N⁴-benzoyl-5'-C-butyl-3'-O-[(tert-butyl)dimethylsilyl]-2'-deoxy-5-methyl-5'-O-(9-phenyl-9H-xanthen-9-yl)cytidine

Chemical Property:

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Technology Process of (5'S)-N⁴-benzoyl-5'-C-butyl-3'-O-[(tert-butyl)dimethylsilyl]-2'-deoxy-5-methyl-5'-O-(9-phenyl-9H-xanthen-9-yl)cytidine

There total 6 articles about (5'S)-N⁴-benzoyl-5'-C-butyl-3'-O-[(tert-butyl)dimethylsilyl]-2'-deoxy-5-methyl-5'-O-(9-phenyl-9H-xanthen-9-yl)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: 87.0%

benzamide (55-21-0,27208-38-4) + (5'S)-5'-C-butyl-3'-O-[(tert-butyl)dimethylsilyl]-4-dehydroxy-5'-O-(9-phenyl-9H-xanthen-9-yl)-4-(1H-1,2,4-triazol-1-yl)thymidine (331822-63-0) → (5'S)-N4-benzoyl-5'-C-butyl-3'-O-[(tert-butyl)dimethylsilyl]-2'-deoxy-5-methyl-5'-O-(9-phenyl-9H-xanthen-9-yl)cytidine (331822-67-4)

Guidance literature:

With potassium hydride; In tetrahydrofuran; at 20 ℃; for 1h;

DOI:10.1002/1522-2675(20010131)84:1<87::AID-HLCA87>3.0.CO;2-1

Reference yield:

pixyl chloride (42506-03-6) → (5'S)-N4-benzoyl-5'-C-butyl-3'-O-[(tert-butyl)dimethylsilyl]-2'-deoxy-5-methyl-5'-O-(9-phenyl-9H-xanthen-9-yl)cytidine (331822-67-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 91 percent / pyridine / 20 °C

2: 87 percent / POCl₃; Et₃N / acetonitrile / 1 h

3: 87 percent / KH / tetrahydrofuran / 1 h / 20 °C

With potassium hydride; triethylamine; trichlorophosphate; In tetrahydrofuran; pyridine; acetonitrile;

DOI:10.1002/1522-2675(20010131)84:1<87::AID-HLCA87>3.0.CO;2-1

Reference yield:

3'-tert-butyldimethylsilylthymidine 5'-carboxaldehyde (131118-61-1) → (5'S)-N4-benzoyl-5'-C-butyl-3'-O-[(tert-butyl)dimethylsilyl]-2'-deoxy-5-methyl-5'-O-(9-phenyl-9H-xanthen-9-yl)cytidine (331822-67-4)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 2M sodium hexamethyldisilazid / tetrahydrofuran / 1 h / Heating

1.2: 65 percent / tetrahydrofuran / 16 h / -78 - 20 °C

2.1: 3-chloroperbenzoic acid / CH₂Cl₂ / 42 h / -38 - -5 °C

2.2: DIBAH / hexane; tetrahydrofuran / 6.5 h / -78 °C

3.1: 91 percent / pyridine / 20 °C

4.1: 87 percent / POCl₃; Et₃N / acetonitrile / 1 h

5.1: 87 percent / KH / tetrahydrofuran / 1 h / 20 °C

With sodium hexamethyldisilazane; potassium hydride; triethylamine; 3-chloro-benzenecarboperoxoic acid; trichlorophosphate; In tetrahydrofuran; pyridine; dichloromethane; acetonitrile;

DOI:10.1002/1522-2675(20010131)84:1<87::AID-HLCA87>3.0.CO;2-1

upstream raw materials:

benzamide

(5'S)-5'-C-butyl-3'-O-[(tert-butyl)dimethylsilyl]-4-dehydroxy-5'-O-(9-phenyl-9H-xanthen-9-yl)-4-(1H-1,2,4-triazol-1-yl)thymidine

pixyl chloride

3'-tert-butyldimethylsilylthymidine 5'-carboxaldehyde

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