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

Base Information

• Chemical Name: (1'R, 3'S, 4'S)-2',3'-dideoxy-3'-tritylamino-N⁴-benzoyl-5-methylcytidin-4'-carboxylic acid
• CAS No.: 1417713-26-8
• Molecular Formula: C₃₆H₃₂N₄O₅
• Molecular Weight: 600.674

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

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

Chemical Property:

Purity/Quality:

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

There total 3 articles about (1'R, 3'S, 4'S)-2',3'-dideoxy-3'-tritylamino-N⁴-benzoyl-5-methylcytidin-4'-carboxylic acid 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: 90.0%

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 (195375-96-3) → (1'R, 3'S, 4'S)-2',3'-dideoxy-3'-tritylamino-N4-benzoyl-5-methylcytidin-4'-carboxylic acid (1417713-26-8)

Guidance literature:

With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene; In water; acetonitrile; at 25 ℃; for 3h;

DOI:10.1016/j.tet.2012.11.028

Reference yield:

N4-benzoyl-5-methyl-3'-amino-5'-O-(tert-butyldimethylsilyl)-2',3'-dideoxycytidine (1417713-33-7) → (1'R, 3'S, 4'S)-2',3'-dideoxy-3'-tritylamino-N4-benzoyl-5-methylcytidin-4'-carboxylic acid (1417713-26-8)

Guidance literature:

Multi-step reaction with 3 steps

1: dmap / pyridine / 8 h / 20 °C

2: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 20 °C

3: [bis(acetoxy)iodo]benzene; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical / acetonitrile; water / 3 h / 25 °C

With dmap; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene; tetrabutyl ammonium fluoride; In tetrahydrofuran; pyridine; water; acetonitrile;

DOI:10.1016/j.tet.2012.11.028

Reference yield:

N4-benzoyl-5-methyl-3'-tritylamino-5'-O-(tert-butyldimethylsilyl)-2',3'-dideoxycytidine (195375-49-6) → (1'R, 3'S, 4'S)-2',3'-dideoxy-3'-tritylamino-N4-benzoyl-5-methylcytidin-4'-carboxylic acid (1417713-26-8)

Guidance literature:

Multi-step reaction with 2 steps

1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 20 °C

2: [bis(acetoxy)iodo]benzene; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical / acetonitrile; water / 3 h / 25 °C

With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene; tetrabutyl ammonium fluoride; In tetrahydrofuran; water; acetonitrile;

DOI:10.1016/j.tet.2012.11.028

upstream 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

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

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

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