N₄-benzoyl-5-methyl-3'-tritylamino-5'-O-(tert-butyldimethylsilyl)-2',3'-dideoxycytidine

Base Information

• Chemical Name: N₄-benzoyl-5-methyl-3'-tritylamino-5'-O-(tert-butyldimethylsilyl)-2',3'-dideoxycytidine
• CAS No.: 195375-49-6
• Molecular Formula: C₄₂H₄₈N₄O₄Si
• Molecular Weight: 700.953

Synonyms:N₄-benzoyl-5-methyl-3'-tritylamino-5'-O-(tert-butyldimethylsilyl)-2',3'-dideoxycytidine

Chemical Property of N₄-benzoyl-5-methyl-3'-tritylamino-5'-O-(tert-butyldimethylsilyl)-2',3'-dideoxycytidine

Chemical Property:

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Technology Process of N₄-benzoyl-5-methyl-3'-tritylamino-5'-O-(tert-butyldimethylsilyl)-2',3'-dideoxycytidine

There total 11 articles about N₄-benzoyl-5-methyl-3'-tritylamino-5'-O-(tert-butyldimethylsilyl)-2',3'-dideoxycytidine 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: 81.0%

benzoyl chloride (98-88-4) + 4-Amino-1-[(2R,4S,5S)-5-(tert-butyl-dimethyl-silanyloxymethyl)-4-(trityl-amino)-tetrahydro-furan-2-yl]-5-methyl-1H-pyrimidin-2-one → N4-benzoyl-5-methyl-3'-tritylamino-5'-O-(tert-butyldimethylsilyl)-2',3'-dideoxycytidine (195375-49-6)

Guidance literature:

In pyridine; for 16h; Ambient temperature;

DOI:10.1021/jo970801t

Reference yield: 78.0%

N4-benzoyl-5-methyl-3'-amino-5'-O-(tert-butyldimethylsilyl)-2',3'-dideoxycytidine (1417713-33-7) + trityl chloride (76-83-5) → N4-benzoyl-5-methyl-3'-tritylamino-5'-O-(tert-butyldimethylsilyl)-2',3'-dideoxycytidine (195375-49-6)

Guidance literature:

With dmap; In pyridine; at 20 ℃; for 8h;

DOI:10.1016/j.tet.2012.11.028

Reference yield:

1-{(2R,4S,5S)-4-azido-5-{{[(1,1-dimethylethyl)dimethylsilyl]oxy}methyl}tetrahydrofuran-2-yl}-5-methylpyrimidine-2,4(1H,3H)-dione (120624-97-7) → N4-benzoyl-5-methyl-3'-tritylamino-5'-O-(tert-butyldimethylsilyl)-2',3'-dideoxycytidine (195375-49-6)

Guidance literature:

Multi-step reaction with 5 steps

1: H₂ / 10percent Pd/C / ethanol; CH₂Cl₂

2: 83 percent / Et₃N / pyridine; CH₂Cl₂ / 2 h / Ambient temperature

3: Et₃N, POCl₃ / acetonitrile / 2 h / Ambient temperature

4: conc.NH₄OH / dioxane / 4 h / Ambient temperature

5: 81 percent / pyridine / 16 h / Ambient temperature

With ammonium hydroxide; hydrogen; triethylamine; trichlorophosphate; palladium on activated charcoal; In 1,4-dioxane; pyridine; ethanol; dichloromethane; acetonitrile;

DOI:10.1021/jo970801t

upstream raw materials:

benzoyl chloride

1-{(2R,4S,5S)-4-azido-5-{{[(1,1-dimethylethyl)dimethylsilyl]oxy}methyl}tetrahydrofuran-2-yl}-5-methylpyrimidine-2,4(1H,3H)-dione

tert-butyldimethylsilyl chloride

5'-tert-butyldimethylsilyloxy-2'-deoxythymidine

Downstream raw materials:

N-{1-[(2R,4S,5S)-5-Hydroxymethyl-4-(trityl-amino)-tetrahydro-furan-2-yl]-5-methyl-2-oxo-1,2-dihydro-pyrimidin-4-yl}-benzamide

(1'R, 3'S, 4'S)-2',3'-dideoxy-3'-tritylamino-N⁴-benzoyl-5-methylcytidin-4'-carboxylic acid

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