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

Base Information

Chemical Name: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
CAS No.:195375-96-3
Molecular Formula:C₃₆H₃₄N₄O₄
Molecular Weight:586.69
Hs Code.:

Synonyms: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

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Chemical Property of 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

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Technology Process of 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

There total 10 articles about 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 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%

: 195375-49-6
N₄-benzoyl-5-methyl-3'-tritylamino-5'-O-(tert-butyldimethylsilyl)-2',3'-dideoxycytidine

: 195375-96-3
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

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; for 16h;
DOI:10.1021/jo970801t

Reference yield:

: 120624-97-7
1-{(2R,4S,5S)-4-azido-5-{{[(1,1-dimethylethyl)dimethylsilyl]oxy}methyl}tetrahydrofuran-2-yl}-5-methylpyrimidine-2,4(1H,3H)-dione

: 195375-96-3
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

Guidance literature:: Multi-step reaction with 6 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

6: 93 percent / TBAF / tetrahydrofuran / 16 h

With ammonium hydroxide; tetrabutyl ammonium fluoride; hydrogen; triethylamine; trichlorophosphate; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; pyridine; ethanol; dichloromethane; acetonitrile;
DOI:10.1021/jo970801t

Reference yield:

: 40733-28-6
5'-tert-butyldimethylsilyloxy-2'-deoxythymidine

: 195375-96-3
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

Guidance literature:: Multi-step reaction with 8 steps

1: Ph₃P, DIAD / dimethylformamide / 2 h / Ambient temperature

2: LiN₃ / dimethylformamide / 48 h / 95 - 100 °C

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

4: 83 percent / Et₃N / pyridine; CH₂Cl₂ / 2 h / Ambient temperature

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

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

7: 81 percent / pyridine / 16 h / Ambient temperature

8: 93 percent / TBAF / tetrahydrofuran / 16 h

With ammonium hydroxide; lithium azide; di-isopropyl azodicarboxylate; tetrabutyl ammonium fluoride; hydrogen; triethylamine; triphenylphosphine; trichlorophosphate; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; pyridine; ethanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1021/jo970801t