1-(3',5'-O-TPDS-2'-O-phenoxythiocarbonyl-β-D-ribofuranosyl-2',3',5'(R/S)-2H3)-thymidine

Base Information

• Chemical Name: 1-(3',5'-O-TPDS-2'-O-phenoxythiocarbonyl-β-D-ribofuranosyl-2',3',5'(R/S)-2H3)-thymidine
• CAS No.: 219569-31-0
• Molecular Formula: C₂₉H₄₄N₂O₈SSi₂
• Molecular Weight: 639.89
• Mol file: 219569-31-0.mol

Synonyms:1-(3',5'-O-TPDS-2'-O-phenoxythiocarbonyl-β-D-ribofuranosyl-2',3',5'(R/S)-2H3)-thymidine

Chemical Property of 1-(3',5'-O-TPDS-2'-O-phenoxythiocarbonyl-β-D-ribofuranosyl-2',3',5'(R/S)-2H3)-thymidine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-(3',5'-O-TPDS-2'-O-phenoxythiocarbonyl-β-D-ribofuranosyl-2',3',5'(R/S)-2H3)-thymidine

There total 12 articles about 1-(3',5'-O-TPDS-2'-O-phenoxythiocarbonyl-β-D-ribofuranosyl-2',3',5'(R/S)-2H3)-thymidine 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: 96.0%

phenylcarbonochloridothioate (1005-56-7) + 1-(3',5'-O-TPDS-β-D-ribofuranosyl-2',3',5'(R/S)-2H3)-thymidine (219569-30-9) → 1-(3',5'-O-TPDS-2'-O-phenoxythiocarbonyl-β-D-ribofuranosyl-2',3',5'(R/S)-2H3)-thymidine (219569-31-0)

Guidance literature:

With 1-methyl-1H-imidazole; In dichloromethane; Ambient temperature;

DOI:10.1016/S0040-4020(98)00905-3

Reference yield:

1,3-Dichloro-1,1,3,3-tetraisopropyldisiloxane (69304-37-6) → 1-(3',5'-O-TPDS-2'-O-phenoxythiocarbonyl-β-D-ribofuranosyl-2',3',5'(R/S)-2H3)-thymidine (219569-31-0)

Guidance literature:

Multi-step reaction with 7 steps

1: 84 percent / Py / 2 h

2: 1.) oxalyl chloride, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -70 deg C, 2.8 h, 2.) -70 deg C, 1 h.

3: NaBD₄ / ethanol / 1 h

4: 74 percent / DMAP, Py / CH₂Cl₂ / 2.5 h / 0 °C

5: 96 percent / dimethylformamide / 4.5 h

6: 67 percent / NH₃ / methanol / 21 h / Ambient temperature

7: 96 percent / 1-N-methylimidazole / CH₂Cl₂ / Ambient temperature

With pyridine; 1-methyl-1H-imidazole; dmap; sodium borodeuteride; oxalyl dichloride; ammonia; dimethyl sulfoxide; triethylamine; In methanol; ethanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4020(98)00905-3

Reference yield:

thymin (65-71-4,28806-14-6,691841-57-3) → 1-(3',5'-O-TPDS-2'-O-phenoxythiocarbonyl-β-D-ribofuranosyl-2',3',5'(R/S)-2H3)-thymidine (219569-31-0)

Guidance literature:

Multi-step reaction with 9 steps

1: 1.) HMDS, TMS-Cl, 2.) trimehtylsilyl trifluoromethanesulfonate / 1.) 120 deg C, 2.) 1,2-dichloroethane, 70 deg C, 4 h.

2: 99 percent / NH₃ / methanol / Ambient temperature

3: 84 percent / Py / 2 h

4: 1.) oxalyl chloride, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -70 deg C, 2.8 h, 2.) -70 deg C, 1 h.

5: NaBD₄ / ethanol / 1 h

6: 74 percent / DMAP, Py / CH₂Cl₂ / 2.5 h / 0 °C

7: 96 percent / dimethylformamide / 4.5 h

8: 67 percent / NH₃ / methanol / 21 h / Ambient temperature

9: 96 percent / 1-N-methylimidazole / CH₂Cl₂ / Ambient temperature

With pyridine; 1-methyl-1H-imidazole; dmap; chloro-trimethyl-silane; sodium borodeuteride; oxalyl dichloride; trimethylsilyl trifluoromethanesulfonate; ammonia; dimethyl sulfoxide; triethylamine; 1,1,1,3,3,3-hexamethyl-disilazane; In methanol; ethanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4020(98)00905-3

upstream raw materials:

phenylcarbonochloridothioate

1-(3',5'-O-TPDS-β-D-ribofuranosyl-2',3',5'(R/S)-2H3)-thymidine

1,3-Dichloro-1,1,3,3-tetraisopropyldisiloxane

thymin