N⁴-benzoyl-3',5'-O-bis(tert-butyldiphenylsilyl)-2'-O-{2-[(N,N-dimethylamino)oxy]ethyl}-5-methylcytidine

Base Information

• Chemical Name: N⁴-benzoyl-3',5'-O-bis(tert-butyldiphenylsilyl)-2'-O-{2-[(N,N-dimethylamino)oxy]ethyl}-5-methylcytidine
• CAS No.: 400821-06-9
• Molecular Formula: C₅₃H₆₄N₄O₇Si₂
• Molecular Weight: 925.285

Synonyms:N⁴-benzoyl-3',5'-O-bis(tert-butyldiphenylsilyl)-2'-O-{2-[(N,N-dimethylamino)oxy]ethyl}-5-methylcytidine

Chemical Property of N⁴-benzoyl-3',5'-O-bis(tert-butyldiphenylsilyl)-2'-O-{2-[(N,N-dimethylamino)oxy]ethyl}-5-methylcytidine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

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Technology Process of N⁴-benzoyl-3',5'-O-bis(tert-butyldiphenylsilyl)-2'-O-{2-[(N,N-dimethylamino)oxy]ethyl}-5-methylcytidine

There total 11 articles about N⁴-benzoyl-3',5'-O-bis(tert-butyldiphenylsilyl)-2'-O-{2-[(N,N-dimethylamino)oxy]ethyl}-5-methylcytidine 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%

benzoic acid anhydride (93-97-0) + 3',5'-O-bis(tert-butyldiphenylsilyl)-2'-O-{2-[(N,N-dimethylamino)oxy]ethyl}-5-methylcytidine (400821-05-8) → N4-benzoyl-3',5'-O-bis(tert-butyldiphenylsilyl)-2'-O-{2-[(N,N-dimethylamino)oxy]ethyl}-5-methylcytidine (400821-06-9)

Guidance literature:

In N,N-dimethyl-formamide; at 20 ℃;

DOI:10.1021/jo0103975

Reference yield:

O-2,2'-cyclo-5-methyluridine (22423-26-3) → N4-benzoyl-3',5'-O-bis(tert-butyldiphenylsilyl)-2'-O-{2-[(N,N-dimethylamino)oxy]ethyl}-5-methylcytidine (400821-06-9)

Guidance literature:

Multi-step reaction with 10 steps

1.1: 74.8 percent / DMAP / pyridine / 16 h / 20 °C

2.1: BH₃*THF; NaHCO₃ / 16 h / 160 °C

3.1: 86 percent / PPh₃; DEAD / tetrahydrofuran / 4 h / 20 °C

4.1: N-methylhydrazine / CH₂Cl₂ / 1 h / -10 - 0 °C

5.1: 7.71 g / methanol; H₂O / 5 h / 20 °C

6.1: pyridinium p-toluenesulfonate; NaBH₃CN / methanol / 0 - 20 °C

7.1: pyridinium p-toluenesulfonate / methanol; H₂O / 0.17 h / 20 °C

7.2: 6.34 g / NaBH₃CN / methanol / 10 - 20 °C

8.1: 85 percent / imidazole / dimethylformamide / 14 h / 60 °C

9.1: 1,2,4-triazole; POCl₃; Et₃N / acetonitrile / 0 - 20 °C

9.2: 94 percent / aq. NH₃ / dioxane / 20 °C

10.1: 87 percent / dimethylformamide / 20 °C

With 1H-imidazole; 1,2,4-Triazole; dmap; borane-THF; pyridinium p-toluenesulfonate; sodium cyanoborohydride; sodium hydrogencarbonate; triethylamine; triphenylphosphine; methylhydrazine; diethylazodicarboxylate; trichlorophosphate; In tetrahydrofuran; pyridine; methanol; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile; 3.1: Mitsunobu reaction;

DOI:10.1021/jo0103975

Reference yield:

tert-butylchlorodiphenylsilane (58479-61-1) → N4-benzoyl-3',5'-O-bis(tert-butyldiphenylsilyl)-2'-O-{2-[(N,N-dimethylamino)oxy]ethyl}-5-methylcytidine (400821-06-9)

Guidance literature:

Multi-step reaction with 10 steps

1.1: 74.8 percent / DMAP / pyridine / 16 h / 20 °C

2.1: BH₃*THF; NaHCO₃ / 16 h / 160 °C

3.1: 86 percent / PPh₃; DEAD / tetrahydrofuran / 4 h / 20 °C

4.1: N-methylhydrazine / CH₂Cl₂ / 1 h / -10 - 0 °C

5.1: 7.71 g / methanol; H₂O / 5 h / 20 °C

6.1: pyridinium p-toluenesulfonate; NaBH₃CN / methanol / 0 - 20 °C

7.1: pyridinium p-toluenesulfonate / methanol; H₂O / 0.17 h / 20 °C

7.2: 6.34 g / NaBH₃CN / methanol / 10 - 20 °C

8.1: 85 percent / imidazole / dimethylformamide / 14 h / 60 °C

9.1: 1,2,4-triazole; POCl₃; Et₃N / acetonitrile / 0 - 20 °C

9.2: 94 percent / aq. NH₃ / dioxane / 20 °C

10.1: 87 percent / dimethylformamide / 20 °C

With 1H-imidazole; 1,2,4-Triazole; dmap; borane-THF; pyridinium p-toluenesulfonate; sodium cyanoborohydride; sodium hydrogencarbonate; triethylamine; triphenylphosphine; methylhydrazine; diethylazodicarboxylate; trichlorophosphate; In tetrahydrofuran; pyridine; methanol; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile; 3.1: Mitsunobu reaction;

DOI:10.1021/jo0103975

upstream raw materials:

benzoic acid anhydride

3',5'-O-bis(tert-butyldiphenylsilyl)-2'-O-{2-[(N,N-dimethylamino)oxy]ethyl}-5-methylcytidine

O-2,2'-cyclo-5-methyluridine

tert-butylchlorodiphenylsilane

Downstream raw materials:

N⁴-benzoyl-2'-O-{2-[(N,N-dimethylamino)oxy]ethyl}-5-methylcytidine

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