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

Base Information

• Chemical Name: (5'S)-N⁴-benzoyl-5'-C-butyl-2'-deoxy-5-methyl-5'-O-(9-phenyl-9H-xanthen-9-yl)cytidine
• CAS No.: 331822-69-6
• Molecular Formula: C₄₀H₃₉N₃O₆
• Molecular Weight: 657.766

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

Chemical Property of (5'S)-N⁴-benzoyl-5'-C-butyl-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-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-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:

pixyl chloride (42506-03-6) → (5'S)-N4-benzoyl-5'-C-butyl-2'-deoxy-5-methyl-5'-O-(9-phenyl-9H-xanthen-9-yl)cytidine (331822-69-6)

Guidance literature:

Multi-step reaction with 4 steps

1: 91 percent / pyridine / 20 °C

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

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

4: 99 percent / 1.0M Bu₄NF / tetrahydrofuran / 20 °C

With tetrabutyl ammonium fluoride; 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-2'-deoxy-5-methyl-5'-O-(9-phenyl-9H-xanthen-9-yl)cytidine (331822-69-6)

Guidance literature:

Multi-step reaction with 6 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

6.1: 99 percent / 1.0M Bu₄NF / tetrahydrofuran / 20 °C

With tetrabutyl ammonium fluoride; 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

Reference yield:

(5'Z)-5'-C-butylidene-3'-O-[(tert-butyl)dimethylsilyl]-5'-deoxythymidine (331822-43-6) → (5'S)-N4-benzoyl-5'-C-butyl-2'-deoxy-5-methyl-5'-O-(9-phenyl-9H-xanthen-9-yl)cytidine (331822-69-6)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 3-chloroperbenzoic acid / CH₂Cl₂ / 42 h / -38 - -5 °C

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

2.1: 91 percent / pyridine / 20 °C

3.1: 87 percent / POCl₃; Et₃N / acetonitrile / 1 h

4.1: 87 percent / KH / tetrahydrofuran / 1 h / 20 °C

5.1: 99 percent / 1.0M Bu₄NF / tetrahydrofuran / 20 °C

With tetrabutyl ammonium fluoride; 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:

pixyl chloride

3'-tert-butyldimethylsilylthymidine 5'-carboxaldehyde

(5'Z)-5'-C-butylidene-3'-O-[(tert-butyl)dimethylsilyl]-5'-deoxythymidine

(5'S)-5'-C-butyl-3'-O-[(tert-butyl)dimethylsilyl]thymidine

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