4'-C-acetoxymethyl-2'-O-acetyl-3'-O-benzyl-5'-O-tert-butyldiphenylsilyl-5-methyluridine

Base Information

Chemical Name:4'-C-acetoxymethyl-2'-O-acetyl-3'-O-benzyl-5'-O-tert-butyldiphenylsilyl-5-methyluridine
CAS No.:519056-21-4
Molecular Formula:C₃₈H₄₄N₂O₉Si
Molecular Weight:700.861
Hs Code.:

Synonyms:4'-C-acetoxymethyl-2'-O-acetyl-3'-O-benzyl-5'-O-tert-butyldiphenylsilyl-5-methyluridine

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Chemical Property of 4'-C-acetoxymethyl-2'-O-acetyl-3'-O-benzyl-5'-O-tert-butyldiphenylsilyl-5-methyluridine

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Technology Process of 4'-C-acetoxymethyl-2'-O-acetyl-3'-O-benzyl-5'-O-tert-butyldiphenylsilyl-5-methyluridine

There total 2 articles about 4'-C-acetoxymethyl-2'-O-acetyl-3'-O-benzyl-5'-O-tert-butyldiphenylsilyl-5-methyluridine 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%

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

: 65-71-4,28806-14-6,691841-57-3
thymin

: 519056-21-4
4'-C-acetoxymethyl-2'-O-acetyl-3'-O-benzyl-5'-O-tert-butyldiphenylsilyl-5-methyluridine

Guidance literature:: With N,O-bis-(trimethylsilyl)-acetamide; trimethylsilyl trifluoromethanesulfonate; In acetonitrile; for 1h; Heating;
DOI:10.1016/j.bmc.2005.09.020

Reference yield:

: 212970-72-4
{3-[(2,2-dimethyl-1,1-diphenyl-1-silapropoxy)methyl]-(1S,3R,4S,5R)-7,7-dimethyl-2,6,8-trioxa-4-(phenylmethoxy)bicyclo[3.3.0]oct-3-yl}methan-1-ol

: 519056-21-4
4'-C-acetoxymethyl-2'-O-acetyl-3'-O-benzyl-5'-O-tert-butyldiphenylsilyl-5-methyluridine

Guidance literature:: Multi-step reaction with 2 steps

1: 99 percent / H₂SO₄; acetic acid / 1 h / 20 °C

2: 93 percent / N,O-bis(trimethylsilyl)acetamide; TMSOTf / acetonitrile / 1 h / Heating

With N,O-bis-(trimethylsilyl)-acetamide; trimethylsilyl trifluoromethanesulfonate; sulfuric acid; acetic acid; In acetonitrile; 2: Vorbrueggen reaction;
DOI:10.1016/j.bmc.2005.09.020

Reference yield:

: 519056-21-4
4'-C-acetoxymethyl-2'-O-acetyl-3'-O-benzyl-5'-O-tert-butyldiphenylsilyl-5-methyluridine

: 877823-51-3
4-N-benzoyl-5-methyl-2'-O,4'-C-(methylenoxymethylene)cytidine

Guidance literature:: Multi-step reaction with 7 steps

1: 90 percent / K₂CO₃ / methanol / 4 h / 20 °C

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

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

4: 246 mg / aq. NH₃ / dioxane / 2 h / 20 °C

5: 87 percent / pyridine / 3.5 h / 20 °C

6: 97 percent / TBAF / tetrahydrofuran / 10 h / 20 °C

7: 68 percent / cyclohexene / Pd/C / tetrahydrofuran / 4 h / Heating

With pyridine; ammonium hydroxide; tetrabutyl ammonium fluoride; potassium carbonate; toluene-4-sulfonic acid; triethylamine; cyclohexene; trichlorophosphate; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; methanol; 1,2-dichloro-ethane; acetonitrile;
DOI:10.1016/j.bmc.2005.09.020