N⁴-benzoyl-3'-O-(tert-butyldimethylsilyl)-5'-O-(4,4'-dimethoxytrityl)-2'-trifluoroacetamido-2'-deoxycytidine

Base Information

• Chemical Name: N⁴-benzoyl-3'-O-(tert-butyldimethylsilyl)-5'-O-(4,4'-dimethoxytrityl)-2'-trifluoroacetamido-2'-deoxycytidine
• CAS No.: 174221-92-2
• Molecular Formula: C₄₅H₄₉F₃N₄O₈Si
• Molecular Weight: 858.987

Synonyms:N⁴-benzoyl-3'-O-(tert-butyldimethylsilyl)-5'-O-(4,4'-dimethoxytrityl)-2'-trifluoroacetamido-2'-deoxycytidine

Chemical Property of N⁴-benzoyl-3'-O-(tert-butyldimethylsilyl)-5'-O-(4,4'-dimethoxytrityl)-2'-trifluoroacetamido-2'-deoxycytidine

Chemical Property:

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Technology Process of N⁴-benzoyl-3'-O-(tert-butyldimethylsilyl)-5'-O-(4,4'-dimethoxytrityl)-2'-trifluoroacetamido-2'-deoxycytidine

There total 10 articles about N⁴-benzoyl-3'-O-(tert-butyldimethylsilyl)-5'-O-(4,4'-dimethoxytrityl)-2'-trifluoroacetamido-2'-deoxycytidine 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: 93.0%

benzoic acid anhydride (93-97-0) + 3'-O-(tert-butyldimethylsilyl)-5'-O-(4,4'-dimethoxytrityl)-2'-trifluoroacetamido-2'-deoxycytidine (174221-91-1) → N4-benzoyl-3'-O-(tert-butyldimethylsilyl)-5'-O-(4,4'-dimethoxytrityl)-2'-trifluoroacetamido-2'-deoxycytidine (174221-92-2)

Guidance literature:

In N,N-dimethyl-formamide; Ambient temperature;

DOI:10.1021/jo9510548

Reference yield:

2,2'-Anhydrouridine (3736-77-4) → N4-benzoyl-3'-O-(tert-butyldimethylsilyl)-5'-O-(4,4'-dimethoxytrityl)-2'-trifluoroacetamido-2'-deoxycytidine (174221-92-2)

Guidance literature:

Multi-step reaction with 8 steps

1: 56 percent / DMAP / pyridine / 16 h / Ambient temperature

2: 43 percent / NaH / 16 h / 90 °C

3: 79 percent / aq. NaOH / ethanol / 16 h / Heating

4: 55 percent / Et₃N / acetonitrile / 16 h / Ambient temperature

5: Et₃N / acetonitrile / 3 h / Ambient temperature

6: phosphorus oxychloride, Et₃N / acetonitrile / 3 h / Ambient temperature

7: 71 percent / NH₄OH / tetrahydrofuran / 6 h / Ambient temperature

8: 93 percent / dimethylformamide / Ambient temperature

With dmap; ammonium hydroxide; sodium hydroxide; sodium hydride; triethylamine; trichlorophosphate; In tetrahydrofuran; pyridine; ethanol; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/jo9510548

Reference yield:

5'-O-(4,4'-dimethoxytrityl)-2'-N,3'-O-(2-(trichloromethyl)oxazolino)-2'-deoxy-1-(β-D-ribofuranosyl)uracil (174221-82-0) → N4-benzoyl-3'-O-(tert-butyldimethylsilyl)-5'-O-(4,4'-dimethoxytrityl)-2'-trifluoroacetamido-2'-deoxycytidine (174221-92-2)

Guidance literature:

Multi-step reaction with 6 steps

1: 79 percent / aq. NaOH / ethanol / 16 h / Heating

2: 55 percent / Et₃N / acetonitrile / 16 h / Ambient temperature

3: Et₃N / acetonitrile / 3 h / Ambient temperature

4: phosphorus oxychloride, Et₃N / acetonitrile / 3 h / Ambient temperature

5: 71 percent / NH₄OH / tetrahydrofuran / 6 h / Ambient temperature

6: 93 percent / dimethylformamide / Ambient temperature

With ammonium hydroxide; sodium hydroxide; triethylamine; trichlorophosphate; In tetrahydrofuran; ethanol; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/jo9510548

upstream raw materials:

benzoic acid anhydride

3'-O-(tert-butyldimethylsilyl)-5'-O-(4,4'-dimethoxytrityl)-2'-trifluoroacetamido-2'-deoxycytidine

2,2'-Anhydrouridine

tert-butyldimethylsilyl chloride

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