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

Base Information

• Chemical Name: N⁴-(N²-acetamidoureido)-5'-O-4,4'-dimethoxytrityl-3'-O-tertbutyldimethylsilyl-5-methyl-2'-deoxycytidine
• CAS No.: 244307-09-3
• Molecular Formula: C₄₀H₅₂N₆O₈Si
• Molecular Weight: 772.974

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

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

Chemical Property:

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

There total 4 articles about N⁴-(N²-acetamidoureido)-5'-O-4,4'-dimethoxytrityl-3'-O-tertbutyldimethylsilyl-5-methyl-2'-deoxycytidine 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: 14.0%

N1-acetyl-N5-hydrocarbohydrazide p-toluene sulfonate + 5'-O-4,4'-dimethoxytrityl-3'-O-tertbutyldimethylsilyl-4-O-triisopropylphenylsulfonyl thymidine (242475-43-0) → N4-(N2-acetamidoureido)-5'-O-4,4'-dimethoxytrityl-3'-O-tertbutyldimethylsilyl-5-methyl-2'-deoxycytidine (244307-09-3)

Guidance literature:

With dmap; triethylamine; In pyridine; at 20 ℃; for 12h;

DOI:10.1080/07328319908044841

Reference yield:

tert-butyldimethylsilyl chloride (18162-48-6) → N4-(N2-acetamidoureido)-5'-O-4,4'-dimethoxytrityl-3'-O-tertbutyldimethylsilyl-5-methyl-2'-deoxycytidine (244307-09-3)

Guidance literature:

Multi-step reaction with 3 steps

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

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

3: 14 percent / Et₃N; DMAP / pyridine / 12 h / 20 °C

With 1H-imidazole; dmap; triethylamine; In pyridine; dichloromethane; 1: silylation / 2: Tosylation / 3: Substitution;

DOI:10.1080/07328319908044841

Reference yield:

5'-O-(4,4'-dimethoxytrityl)-3'-O-(t-butyldimethylsilyl)-2'-deoxythymidine (80971-33-1) → N4-(N2-acetamidoureido)-5'-O-4,4'-dimethoxytrityl-3'-O-tertbutyldimethylsilyl-5-methyl-2'-deoxycytidine (244307-09-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 52 percent / Et₃N; DMAP / CH₂Cl₂ / 18 h / 20 °C

2: 14 percent / Et₃N; DMAP / pyridine / 12 h / 20 °C

With dmap; triethylamine; In pyridine; dichloromethane; 1: Tosylation / 2: Substitution;

DOI:10.1080/07328319908044841

upstream raw materials:

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

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

tert-butyldimethylsilyl chloride

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

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