5-[2-(tert-butyldimethylsilanyloxy)ethyl]-2',3',5'-tri-O-benzoyluridine

Base Information

Chemical Name:5-[2-(tert-butyldimethylsilanyloxy)ethyl]-2',3',5'-tri-O-benzoyluridine
CAS No.:752232-89-6
Molecular Formula:C₃₈H₄₂N₂O₁₀Si
Molecular Weight:714.844
Hs Code.:

Synonyms:5-[2-(tert-butyldimethylsilanyloxy)ethyl]-2',3',5'-tri-O-benzoyluridine

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Chemical Property of 5-[2-(tert-butyldimethylsilanyloxy)ethyl]-2',3',5'-tri-O-benzoyluridine

Chemical Property:

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Technology Process of 5-[2-(tert-butyldimethylsilanyloxy)ethyl]-2',3',5'-tri-O-benzoyluridine

There total 2 articles about 5-[2-(tert-butyldimethylsilanyloxy)ethyl]-2',3',5'-tri-O-benzoyluridine 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: 68.0%

: 6974-32-9
1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose

: 18162-48-6
tert-butyldimethylsilyl chloride

: 752232-85-2
5-[2-(tert-butyldimethylsilanyloxy)ethyl]-uracil

: 752232-89-6
5-[2-(tert-butyldimethylsilanyloxy)ethyl]-2',3',5'-tri-O-benzoyluridine

Guidance literature:: 1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose; 5-[2-(tert-butyldimethylsilanyloxy)ethyl]-uracil; With chloro-trimethyl-silane; tin(IV) chloride; 1,1,1,3,3,3-hexamethyl-disilazane; In acetonitrile; at 20 ℃; for 16h;

tert-butyldimethylsilyl chloride; With 1H-imidazole; In N,N-dimethyl-formamide; for 24h;
DOI:10.1039/b404150j

Reference yield:

: 18162-48-6
tert-butyldimethylsilyl chloride

: 752232-89-6
5-[2-(tert-butyldimethylsilanyloxy)ethyl]-2',3',5'-tri-O-benzoyluridine

Guidance literature:: Multi-step reaction with 2 steps

1.1: 97.7 percent / imidazole / dimethylformamide / 15 h / 20 °C

2.1: hexamethyldisilazane; Me₃SiCl; SnCl₄ / acetonitrile / 16 h / 20 °C

2.2: 68 percent / imidazole / dimethylformamide / 24 h

With 1H-imidazole; chloro-trimethyl-silane; tin(IV) chloride; 1,1,1,3,3,3-hexamethyl-disilazane; In N,N-dimethyl-formamide; acetonitrile;
DOI:10.1039/b404150j

Reference yield:

: 752232-89-6
5-[2-(tert-butyldimethylsilanyloxy)ethyl]-2',3',5'-tri-O-benzoyluridine

: 752233-00-4
5-[15-trifluoroacetamido-3,7,12-tris-(N-trifluoroacetyl)-3,7,12-triazapentadecyl]-5'-O-(4,4'-dimethoxytrityl)-2'-O-tert-butyldimethylsilyl-uridine

Guidance literature:: Multi-step reaction with 8 steps

1: 82 percent / NH₃ / methanol / 30 h / 20 °C

2: 74 percent / pyridine / 19 h / 20 °C

3: 98 percent / TBAF / tetrahydrofuran / 20 °C

4: 61 percent / oxalyl chloride; DMSO; TEA / CH₂Cl₂ / 0.33 h / -60 °C

5: pyridine / methanol / 15 h / 20 °C

6: NaBH₄ / methanol / 1 h

7: 0.75 g / pyridine; DMAP / 1 h / 20 °C

8: 69 percent / pyridine; silver nitrate / tetrahydrofuran / 0.5 h / 20 °C

With pyridine; dmap; sodium tetrahydroborate; oxalyl dichloride; TEA; tetrabutyl ammonium fluoride; ammonia; silver nitrate; dimethyl sulfoxide; In tetrahydrofuran; methanol; dichloromethane; 4: Swern oxidation;
DOI:10.1039/b404150j