3'-O-tert-butyldimethylsilyl-5'-O-tert-butyldiphenylsilyl-4'-C-phenoxymethylenethymidine

Base Information

• Chemical Name: 3'-O-tert-butyldimethylsilyl-5'-O-tert-butyldiphenylsilyl-4'-C-phenoxymethylenethymidine
• CAS No.: 851345-94-3
• Molecular Formula: C₃₉H₅₂N₂O₆Si₂
• Molecular Weight: 701.023

Synonyms:3'-O-tert-butyldimethylsilyl-5'-O-tert-butyldiphenylsilyl-4'-C-phenoxymethylenethymidine

Chemical Property of 3'-O-tert-butyldimethylsilyl-5'-O-tert-butyldiphenylsilyl-4'-C-phenoxymethylenethymidine

Chemical Property:

Purity/Quality:

Safty Information:

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Technology Process of 3'-O-tert-butyldimethylsilyl-5'-O-tert-butyldiphenylsilyl-4'-C-phenoxymethylenethymidine

There total 2 articles about 3'-O-tert-butyldimethylsilyl-5'-O-tert-butyldiphenylsilyl-4'-C-phenoxymethylenethymidine 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:

trifluoro-methanesulfonic acid 3-(tert-butyl-dimethyl-silanyloxy)-2-(tert-butyl-diphenyl-silanyloxymethyl)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester + phenol (108-95-2,27073-41-2) → 3'-O-tert-butyldimethylsilyl-5'-O-tert-butyldiphenylsilyl-4'-C-phenoxymethylenethymidine (851345-94-3)

Guidance literature:

phenol; With sodium hydride; In N,N-dimethyl-formamide; at -78 - 0 ℃; for 1.5h;

trifluoro-methanesulfonic acid 3-(tert-butyl-dimethyl-silanyloxy)-2-(tert-butyl-diphenyl-silanyloxymethyl)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester; In N,N-dimethyl-formamide; at 0 - 50 ℃; for 2.5h;

DOI:10.1002/chem.200401114

Reference yield:

1-[(2R,4S,5R)-4-(tert-Butyl-dimethyl-silanyloxy)-5-(tert-butyl-diphenyl-silanyloxymethyl)-5-hydroxymethyl-tetrahydro-furan-2-yl]-5-methyl-1H-pyrimidine-2,4-dione (162052-67-7) → 3'-O-tert-butyldimethylsilyl-5'-O-tert-butyldiphenylsilyl-4'-C-phenoxymethylenethymidine (851345-94-3)

Guidance literature:

Multi-step reaction with 2 steps

1.1: pyridine / CH₂Cl₂ / 1.5 h / 0 °C

2.1: NaH / dimethylformamide / 1.5 h / -78 - 0 °C

2.2: 98.4 mg / dimethylformamide / 2.5 h / 0 - 50 °C

With pyridine; sodium hydride; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1002/chem.200401114

Reference yield: 93.0%

3'-O-tert-butyldimethylsilyl-5'-O-tert-butyldiphenylsilyl-4'-C-phenoxymethylenethymidine (851345-94-3) → 1-((2R,4S,5S)-4-Hydroxy-5-hydroxymethyl-5-phenoxymethyl-tetrahydro-furan-2-yl)-5-methyl-1H-pyrimidine-2,4-dione (851345-95-4)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 1h;

DOI:10.1002/chem.200401114

upstream raw materials:

phenol

1-[(2R,4S,5R)-4-(tert-Butyl-dimethyl-silanyloxy)-5-(tert-butyl-diphenyl-silanyloxymethyl)-5-hydroxymethyl-tetrahydro-furan-2-yl]-5-methyl-1H-pyrimidine-2,4-dione

Downstream raw materials:

1-((2R,4S,5S)-4-Hydroxy-5-hydroxymethyl-5-phenoxymethyl-tetrahydro-furan-2-yl)-5-methyl-1H-pyrimidine-2,4-dione

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