(5'S)-N⁴-benzoyl-2'-deoxy-5-methyl-5'-C-(3-methylbutyl)-5'-O-(9-phenyl-9H-xanthen-9-yl)cytidine

Base Information

• Chemical Name: (5'S)-N⁴-benzoyl-2'-deoxy-5-methyl-5'-C-(3-methylbutyl)-5'-O-(9-phenyl-9H-xanthen-9-yl)cytidine
• CAS No.: 331822-70-9
• Molecular Formula: C₄₁H₄₁N₃O₆
• Molecular Weight: 671.793

Synonyms:(5'S)-N⁴-benzoyl-2'-deoxy-5-methyl-5'-C-(3-methylbutyl)-5'-O-(9-phenyl-9H-xanthen-9-yl)cytidine

Chemical Property of (5'S)-N⁴-benzoyl-2'-deoxy-5-methyl-5'-C-(3-methylbutyl)-5'-O-(9-phenyl-9H-xanthen-9-yl)cytidine

Chemical Property:

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Technology Process of (5'S)-N⁴-benzoyl-2'-deoxy-5-methyl-5'-C-(3-methylbutyl)-5'-O-(9-phenyl-9H-xanthen-9-yl)cytidine

There total 9 articles about (5'S)-N⁴-benzoyl-2'-deoxy-5-methyl-5'-C-(3-methylbutyl)-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-2'-deoxy-5-methyl-5'-C-(3-methylbutyl)-5'-O-(9-phenyl-9H-xanthen-9-yl)cytidine (331822-70-9)

Guidance literature:

Multi-step reaction with 5 steps

1: 87 percent / pyridine / 20 °C

2: 91 percent / POCl₃; Et₃N / acetonitrile / 1 h

3: 100 percent / 25 percent aq. NH₃ / dioxane / 2 h / 20 °C

4: 70 percent / pyridine / 35 h / 0 - 20 °C

5: 100 percent / 1.0M Bu₄NF / tetrahydrofuran / 20 °C

With ammonium hydroxide; tetrabutyl ammonium fluoride; triethylamine; trichlorophosphate; In tetrahydrofuran; 1,4-dioxane; pyridine; acetonitrile;

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

Reference yield:

isoamyltriphenylphosphonium bromide (28322-40-9) → (5'S)-N4-benzoyl-2'-deoxy-5-methyl-5'-C-(3-methylbutyl)-5'-O-(9-phenyl-9H-xanthen-9-yl)cytidine (331822-70-9)

Guidance literature:

Multi-step reaction with 8 steps

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

1.2: 54 percent / tetrahydrofuran / 16 h / -78 - 20 °C

2.1: 57 percent / 3-chloroperbenzoic acid / CH₂Cl₂ / 72 h / -7 °C

3.1: 68 percent / 1M DIBAH / tetrahydrofuran / 6.5 h / -78 °C

4.1: 87 percent / pyridine / 20 °C

5.1: 91 percent / POCl₃; Et₃N / acetonitrile / 1 h

6.1: 100 percent / 25 percent aq. NH₃ / dioxane / 2 h / 20 °C

7.1: 70 percent / pyridine / 35 h / 0 - 20 °C

8.1: 100 percent / 1.0M Bu₄NF / tetrahydrofuran / 20 °C

With ammonium hydroxide; tetrabutyl ammonium fluoride; sodium hexamethyldisilazane; diisobutylaluminium hydride; triethylamine; 3-chloro-benzenecarboperoxoic acid; trichlorophosphate; In tetrahydrofuran; 1,4-dioxane; pyridine; dichloromethane; 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-2'-deoxy-5-methyl-5'-C-(3-methylbutyl)-5'-O-(9-phenyl-9H-xanthen-9-yl)cytidine (331822-70-9)

Guidance literature:

Multi-step reaction with 8 steps

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

1.2: 54 percent / tetrahydrofuran / 16 h / -78 - 20 °C

2.1: 57 percent / 3-chloroperbenzoic acid / CH₂Cl₂ / 72 h / -7 °C

3.1: 68 percent / 1M DIBAH / tetrahydrofuran / 6.5 h / -78 °C

4.1: 87 percent / pyridine / 20 °C

5.1: 91 percent / POCl₃; Et₃N / acetonitrile / 1 h

6.1: 100 percent / 25 percent aq. NH₃ / dioxane / 2 h / 20 °C

7.1: 70 percent / pyridine / 35 h / 0 - 20 °C

8.1: 100 percent / 1.0M Bu₄NF / tetrahydrofuran / 20 °C

With ammonium hydroxide; tetrabutyl ammonium fluoride; sodium hexamethyldisilazane; diisobutylaluminium hydride; triethylamine; 3-chloro-benzenecarboperoxoic acid; trichlorophosphate; In tetrahydrofuran; 1,4-dioxane; pyridine; dichloromethane; acetonitrile;

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

upstream raw materials:

pixyl chloride

isoamyltriphenylphosphonium bromide

3'-tert-butyldimethylsilylthymidine 5'-carboxaldehyde

(5'Z)-3'-O-[(tert-butyl)dimethylsilyl]-2'-deoxy-5'-C-(3-methylbutylidene)thymidine

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