3'-O-t-butyldimethylsilyl-5'-O-dimethoxytrityl-1-[4-(N-methylguanidine)-5-methylpyrimidin-2(1H)-onyl]-β-D-2'-deoxyriboside

Base Information

• Chemical Name: 3'-O-t-butyldimethylsilyl-5'-O-dimethoxytrityl-1-[4-(N-methylguanidine)-5-methylpyrimidin-2(1H)-onyl]-β-D-2'-deoxyriboside
• CAS No.: 328311-89-3
• Molecular Formula: C₃₉H₅₁N₅O₆Si
• Molecular Weight: 713.949
• Mol file: 328311-89-3.mol

Synonyms:3'-O-t-butyldimethylsilyl-5'-O-dimethoxytrityl-1-[4-(N-methylguanidine)-5-methylpyrimidin-2(1H)-onyl]-β-D-2'-deoxyriboside

Chemical Property of 3'-O-t-butyldimethylsilyl-5'-O-dimethoxytrityl-1-[4-(N-methylguanidine)-5-methylpyrimidin-2(1H)-onyl]-β-D-2'-deoxyriboside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3'-O-t-butyldimethylsilyl-5'-O-dimethoxytrityl-1-[4-(N-methylguanidine)-5-methylpyrimidin-2(1H)-onyl]-β-D-2'-deoxyriboside

There total 4 articles about 3'-O-t-butyldimethylsilyl-5'-O-dimethoxytrityl-1-[4-(N-methylguanidine)-5-methylpyrimidin-2(1H)-onyl]-β-D-2'-deoxyriboside 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: 60.0%

N-methylguanidine hydrochloride + 3'-O-t-butyldimethylsilyl-5'-O-dimethoxytrityl-1-[5-methyl-4-triazolylpyrimidin-2(1H)-onyl]-β-D-2'-deoxyriboside (80971-34-2) → 3'-O-t-butyldimethylsilyl-5'-O-dimethoxytrityl-1-[4-(N-methylguanidine)-5-methylpyrimidin-2(1H)-onyl]-β-D-2'-deoxyriboside (328311-89-3)

Guidance literature:

With potassium carbonate; In N,N-dimethyl-formamide; at 100 ℃; for 3h;

DOI:10.1016/S0040-4020(00)00991-1

Reference yield:

5'-O-(4,4'-dimethoxytrityl)-3'-O-(t-butyldimethylsilyl)-2'-deoxythymidine (80971-33-1) → 3'-O-t-butyldimethylsilyl-5'-O-dimethoxytrityl-1-[4-(N-methylguanidine)-5-methylpyrimidin-2(1H)-onyl]-β-D-2'-deoxyriboside (328311-89-3)

Guidance literature:

Multi-step reaction with 2 steps

1.1: POCl₃; Et₃N / acetonitrile / 0.5 h / 0 °C

1.2: acetonitrile / 0 - 20 °C

2.1: 60 percent / K₂CO₃ / dimethylformamide / 3 h / 100 °C

With potassium carbonate; triethylamine; trichlorophosphate; In N,N-dimethyl-formamide; acetonitrile;

DOI:10.1016/S0040-4020(00)00991-1

Reference yield:

tert-butyldimethylsilyl chloride (18162-48-6) → 3'-O-t-butyldimethylsilyl-5'-O-dimethoxytrityl-1-[4-(N-methylguanidine)-5-methylpyrimidin-2(1H)-onyl]-β-D-2'-deoxyriboside (328311-89-3)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 97 percent / imidazole / pyridine / 6 h

2.1: POCl₃; Et₃N / acetonitrile / 0.5 h / 0 °C

2.2: acetonitrile / 0 - 20 °C

3.1: 60 percent / K₂CO₃ / dimethylformamide / 3 h / 100 °C

With 1H-imidazole; potassium carbonate; triethylamine; trichlorophosphate; In pyridine; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1016/S0040-4020(00)00991-1

upstream raw materials:

3'-O-t-butyldimethylsilyl-5'-O-dimethoxytrityl-1-[5-methyl-4-triazolylpyrimidin-2(1H)-onyl]-β-D-2'-deoxyriboside

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

tert-butyldimethylsilyl chloride

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

Downstream raw materials:

5'-O-dimethoxytrityl-1-[4-(N-methylguanidine)-5-methylpyrimidin-2(1H)-onyl]-β-D-2'-deoxyriboside