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

Base Information

• Chemical Name: 3'-O-tert-butyldimethylsilyl-5'-O-tert-butyldiphenylsilyl-4'-C-methoxymethylenethymidine
• CAS No.: 851345-90-9
• Molecular Formula: C₃₄H₅₀N₂O₆Si₂
• Molecular Weight: 638.952

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

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

Chemical Property:

Purity/Quality:

Safty Information:

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

There total 1 articles about 3'-O-tert-butyldimethylsilyl-5'-O-tert-butyldiphenylsilyl-4'-C-methoxymethylenethymidine 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: 75.0%

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) + methyl iodide (74-88-4) → 3'-O-tert-butyldimethylsilyl-5'-O-tert-butyldiphenylsilyl-4'-C-methoxymethylenethymidine (851345-90-9)

Guidance literature:

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; With sodium hydride; In tetrahydrofuran; at 0 ℃; for 0.5h;

methyl iodide; In tetrahydrofuran; at 0 ℃; for 10h;

DOI:10.1002/chem.200401114

Reference yield: 89.0%

3'-O-tert-butyldimethylsilyl-5'-O-tert-butyldiphenylsilyl-4'-C-methoxymethylenethymidine (851345-90-9) → 5'-O-tert-butyldiphenylsilyl-4'-C-methoxymethylene thymidine (950685-77-5)

Guidance literature:

With boron trifluoride diethyl etherate; In dichloromethane; at 20 ℃; for 4h;

DOI:10.1002/chem.200601627

Reference yield:

3'-O-tert-butyldimethylsilyl-5'-O-tert-butyldiphenylsilyl-4'-C-methoxymethylenethymidine (851345-90-9) + 2,4,6-triisopropylphenylsulfonyl chloride (6553-96-4) → 2,4,6-triisopropyl-benzenesulfonic acid 1-[4-(tert-butyl-dimethyl-silanyloxy)-5-(tert-butyl-diphenyl-silanyloxymethyl)-5-methoxymethyl-tetrahydro-furan-2-yl]-5-methyl-2-oxo-1,2-dihydro-pyrimidin-4-yl ester

Guidance literature:

With dmap; triethylamine; In acetonitrile; at 0 ℃; for 1.5h;

DOI:10.1002/chem.200401114

upstream raw materials:

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

methyl iodide

Downstream raw materials:

5'-O-tert-butyldiphenylsilyl-4'-C-methoxymethylene thymidine

2-thio-3'-O-acetyl-4'-C-methoxymethylene thymidine

4-amino-1-[4-(tert-butyl-dimethyl-silanyloxy)-5-(tert-butyl-diphenyl-silanyloxymethyl)-5-methoxymethyl-tetrahydro-furan-2-yl]-5-methyl-1H-pyrimidin-2-one

4-N-benzoyl-3'-O-tert-butyldimethylsilyl-5'-O-tert-butyldiphenylsilyl-4'-C-methoxymethyl-5-methylcytidine

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