4-N-benzoyl-3'-O-benzyl-5-methyl-2'-O,4'-C-(methylenoxymethylene)cytidine

Base Information

Chemical Name:4-N-benzoyl-3'-O-benzyl-5-methyl-2'-O,4'-C-(methylenoxymethylene)cytidine
CAS No.:877823-50-2
Molecular Formula:C₂₆H₂₇N₃O₇
Molecular Weight:493.516
Hs Code.:

Synonyms:4-N-benzoyl-3'-O-benzyl-5-methyl-2'-O,4'-C-(methylenoxymethylene)cytidine

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Chemical Property of 4-N-benzoyl-3'-O-benzyl-5-methyl-2'-O,4'-C-(methylenoxymethylene)cytidine

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Technology Process of 4-N-benzoyl-3'-O-benzyl-5-methyl-2'-O,4'-C-(methylenoxymethylene)cytidine

There total 9 articles about 4-N-benzoyl-3'-O-benzyl-5-methyl-2'-O,4'-C-(methylenoxymethylene)cytidine 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: 97.0%

: 877823-49-9
4-N-benzoyl-3'-O-benzyl-5'-O-tert-butyldiphenylsilyl-5-methyl-2'-O,4'-C-(methylenoxymethylene)cytidine

: 877823-50-2
4-N-benzoyl-3'-O-benzyl-5-methyl-2'-O,4'-C-(methylenoxymethylene)cytidine

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 10h;
DOI:10.1016/j.bmc.2005.09.020

Reference yield:

: 583829-86-1
4-C-acetoxymethyl-1,2-di-O-acetyl-3-O-benzyl-5-O-tert-butyldiphenylsilyl-D-erythro-pentofuranose

: 877823-50-2
4-N-benzoyl-3'-O-benzyl-5-methyl-2'-O,4'-C-(methylenoxymethylene)cytidine

Guidance literature:: Multi-step reaction with 7 steps

1: 93 percent / N,O-bis(trimethylsilyl)acetamide; TMSOTf / acetonitrile / 1 h / Heating

2: 90 percent / K₂CO₃ / methanol / 4 h / 20 °C

3: 81 percent / TsOH*H₂O / 1,2-dichloro-ethane / 3 h / Heating

4: POCl₃; triethylamine / acetonitrile / 5.5 h / 20 °C

5: 246 mg / aq. NH₃ / dioxane / 2 h / 20 °C

6: 87 percent / pyridine / 3.5 h / 20 °C

7: 97 percent / TBAF / tetrahydrofuran / 10 h / 20 °C

With pyridine; ammonium hydroxide; N,O-bis-(trimethylsilyl)-acetamide; trimethylsilyl trifluoromethanesulfonate; tetrabutyl ammonium fluoride; potassium carbonate; toluene-4-sulfonic acid; triethylamine; trichlorophosphate; In tetrahydrofuran; 1,4-dioxane; methanol; 1,2-dichloro-ethane; acetonitrile; 1: Vorbrueggen reaction;
DOI:10.1016/j.bmc.2005.09.020

Reference yield:

: 519056-22-5
3'-O-benzyl-5'-O-tert-butyldiphenylsilyl-4'-C-hydroxymethyl-5-methyluridine

: 877823-50-2
4-N-benzoyl-3'-O-benzyl-5-methyl-2'-O,4'-C-(methylenoxymethylene)cytidine

Guidance literature:: Multi-step reaction with 5 steps

1: 81 percent / TsOH*H₂O / 1,2-dichloro-ethane / 3 h / Heating

2: POCl₃; triethylamine / acetonitrile / 5.5 h / 20 °C

3: 246 mg / aq. NH₃ / dioxane / 2 h / 20 °C

4: 87 percent / pyridine / 3.5 h / 20 °C

5: 97 percent / TBAF / tetrahydrofuran / 10 h / 20 °C

With pyridine; ammonium hydroxide; tetrabutyl ammonium fluoride; toluene-4-sulfonic acid; triethylamine; trichlorophosphate; In tetrahydrofuran; 1,4-dioxane; 1,2-dichloro-ethane; acetonitrile;
DOI:10.1016/j.bmc.2005.09.020