1-[(2R)-3,5-O-(di-tert-butylsilylene)-2-deoxy-2-phenylseleno-4-thio-β-D-ribofuranosyl]thymine

Base Information

Chemical Name:1-[(2R)-3,5-O-(di-tert-butylsilylene)-2-deoxy-2-phenylseleno-4-thio-β-D-ribofuranosyl]thymine
CAS No.:209048-66-8
Molecular Formula:C₂₄H₃₄N₂O₄SSeSi
Molecular Weight:553.656
Hs Code.:

Synonyms:1-[(2R)-3,5-O-(di-tert-butylsilylene)-2-deoxy-2-phenylseleno-4-thio-β-D-ribofuranosyl]thymine

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Chemical Property of 1-[(2R)-3,5-O-(di-tert-butylsilylene)-2-deoxy-2-phenylseleno-4-thio-β-D-ribofuranosyl]thymine

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Technology Process of 1-[(2R)-3,5-O-(di-tert-butylsilylene)-2-deoxy-2-phenylseleno-4-thio-β-D-ribofuranosyl]thymine

There total 10 articles about 1-[(2R)-3,5-O-(di-tert-butylsilylene)-2-deoxy-2-phenylseleno-4-thio-β-D-ribofuranosyl]thymine 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: 62.0%

: 5707-04-0
Phenylselenyl chloride

: 209048-62-4
1,4-anhydro-2-deoxy-3,5-O-(di-tert-butylsilylene)-4-thio-D-erythro-pento-1-enitol

: 7288-28-0
2,4-bis(trimethylsiloxy)-5-methylpyrimidine

: 209048-66-8
1-[(2R)-3,5-O-(di-tert-butylsilylene)-2-deoxy-2-phenylseleno-4-thio-β-D-ribofuranosyl]thymine

Guidance literature:: In acetonitrile;
DOI:10.1016/S0040-4039(98)00543-7

Reference yield:

: 134700-25-7
(2R,3S)-5-(benzylthio)-2-(hydroxymethyl)tetrahydrothiophen-3-ol

: 209048-66-8
1-[(2R)-3,5-O-(di-tert-butylsilylene)-2-deoxy-2-phenylseleno-4-thio-β-D-ribofuranosyl]thymine

Guidance literature:: Multi-step reaction with 8 steps

1: 5.46 g / imidazole; DMF / 20 °C

2: acetic acid / 2 h / 20 °C

3: 670 mg / ammonia / methanol / 20 °C

4: 4-dimethylaminopyridine / CH₂Cl₂ / 0 °C

5: 113 mg / CH₂Cl₂ / 20 °C

6: tetrabutylammonium fluoride / tetrahydrofuran / 0.5 h / 0 °C

7: 30.9 mg / 4-(dimethylamino)pyridine; DMF / 0 °C

8: 62 percent / acetonitrile / 0 °C

With 1H-imidazole; dmap; tetrabutyl ammonium fluoride; ammonia; acetic acid; N,N-dimethyl-formamide; In tetrahydrofuran; methanol; dichloromethane; acetonitrile;
DOI:10.1021/jo020037x

Reference yield:

: 3,5-bis-O-(tert-butyldimethylsilyl)-2-deoxy-1,4-dithio-D-erythro-pentofuranose

: 209048-66-8
1-[(2R)-3,5-O-(di-tert-butylsilylene)-2-deoxy-2-phenylseleno-4-thio-β-D-ribofuranosyl]thymine

Guidance literature:: Multi-step reaction with 5 steps

1: 4-dimethylaminopyridine / CH₂Cl₂ / 0 °C

2: 113 mg / CH₂Cl₂ / 20 °C

3: tetrabutylammonium fluoride / tetrahydrofuran / 0.5 h / 0 °C

4: 30.9 mg / 4-(dimethylamino)pyridine; DMF / 0 °C

5: 62 percent / acetonitrile / 0 °C

With dmap; tetrabutyl ammonium fluoride; N,N-dimethyl-formamide; In tetrahydrofuran; dichloromethane; acetonitrile;
DOI:10.1021/jo020037x