5'-O-4,4'-dimethoxytrityl-3'-O-tertbutyldimethylsilyl-4-O-triisopropylphenylsulfonyl thymidine

Base Information

• Chemical Name: 5'-O-4,4'-dimethoxytrityl-3'-O-tertbutyldimethylsilyl-4-O-triisopropylphenylsulfonyl thymidine
• CAS No.: 242475-43-0
• Molecular Formula: C₅₂H₆₈N₂O₉SSi
• Molecular Weight: 925.271
• Mol file: 242475-43-0.mol

Synonyms:5'-O-4,4'-dimethoxytrityl-3'-O-tertbutyldimethylsilyl-4-O-triisopropylphenylsulfonyl thymidine

Chemical Property of 5'-O-4,4'-dimethoxytrityl-3'-O-tertbutyldimethylsilyl-4-O-triisopropylphenylsulfonyl thymidine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5'-O-4,4'-dimethoxytrityl-3'-O-tertbutyldimethylsilyl-4-O-triisopropylphenylsulfonyl thymidine

There total 7 articles about 5'-O-4,4'-dimethoxytrityl-3'-O-tertbutyldimethylsilyl-4-O-triisopropylphenylsulfonyl 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: 52.0%

2,4,6-triisopropylphenylsulfonyl chloride (6553-96-4) + 5'-O-(4,4'-dimethoxytrityl)-3'-O-(t-butyldimethylsilyl)-2'-deoxythymidine (80971-33-1) → 5'-O-4,4'-dimethoxytrityl-3'-O-tertbutyldimethylsilyl-4-O-triisopropylphenylsulfonyl thymidine (242475-43-0)

Guidance literature:

With dmap; triethylamine; In dichloromethane; at 20 ℃; for 18h;

DOI:10.1080/07328319908044841

Reference yield: 50.0%

2,4,6-triisopropylphenylsulfonyl chloride (6553-96-4) + 5'-O-(4,4'-dimethoxytrityl)-3'-O-(t-butyldimethylsilyl)-2'-deoxythymidine (80971-33-1) → C52H68N2O9SSi + 5'-O-4,4'-dimethoxytrityl-3'-O-tertbutyldimethylsilyl-4-O-triisopropylphenylsulfonyl thymidine (242475-43-0)

Guidance literature:

With dmap; triethylamine; In dichloromethane; at 20 ℃; Inert atmosphere;

DOI:10.1093/nar/gkv285

Reference yield:

tert-butyldimethylsilyl chloride (18162-48-6) → 5'-O-4,4'-dimethoxytrityl-3'-O-tertbutyldimethylsilyl-4-O-triisopropylphenylsulfonyl thymidine (242475-43-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 95 percent / Et₃N; imidazole / pyridine / 12 h / 20 °C

2: 52 percent / Et₃N; DMAP / CH₂Cl₂ / 18 h / 20 °C

With 1H-imidazole; dmap; triethylamine; In pyridine; dichloromethane; 1: silylation / 2: Tosylation;

DOI:10.1080/07328319908044841

upstream raw materials:

2,4,6-triisopropylphenylsulfonyl chloride

5'-O-(4,4'-dimethoxytrityl)-3'-O-(t-butyldimethylsilyl)-2'-deoxythymidine

tert-butyldimethylsilyl chloride

5'-O-(4-4'-dimethoxytrityl)thymidine

Downstream raw materials:

N⁴-ureido-5'-O-4,4'-dimethoxytrityl-5-methyl-2'-deoxycytidine

N⁴-(N²-acetamidoureido)-5'-O-4,4'-dimethoxytrityl-3'-O-tertbutyldimethylsilyl-5-methyl-2'-deoxycytidine

N⁴-ureido-5'-O-4,4'-dimethoxytrityl-3'-O-tertbutyldimethylsilyl-5-methyl-2'-deoxycytidine

Refernces

• 1、 Gianolio, Diego A.,McLaughlin, Larry W.. "Synthesis and triplex forming properties of pyrimidine derivative containing extended functionality". . p. 1751 - 1769. Retrieved 2007/10/03.