N₂-isobutyryl-2'-O-(N,N'-di-Boc-N'-isobutyryl-guanidinopropyl)-5'-O-(4,4'-dimethoxytrityl)-guanosine

Base Information

• Chemical Name: N₂-isobutyryl-2'-O-(N,N'-di-Boc-N'-isobutyryl-guanidinopropyl)-5'-O-(4,4'-dimethoxytrityl)-guanosine
• CAS No.: 1360744-44-0
• Molecular Formula: C₅₃H₆₈N₈O₁₃
• Molecular Weight: 1025.17

Synonyms:N₂-isobutyryl-2'-O-(N,N'-di-Boc-N'-isobutyryl-guanidinopropyl)-5'-O-(4,4'-dimethoxytrityl)-guanosine

Chemical Property of N₂-isobutyryl-2'-O-(N,N'-di-Boc-N'-isobutyryl-guanidinopropyl)-5'-O-(4,4'-dimethoxytrityl)-guanosine

Chemical Property:

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Technology Process of N₂-isobutyryl-2'-O-(N,N'-di-Boc-N'-isobutyryl-guanidinopropyl)-5'-O-(4,4'-dimethoxytrityl)-guanosine

There total 5 articles about N₂-isobutyryl-2'-O-(N,N'-di-Boc-N'-isobutyryl-guanidinopropyl)-5'-O-(4,4'-dimethoxytrityl)-guanosine 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:

2'-O-(3-(N,N'-di-tert-butoxycarbonylguanidino)propyl)-3',5'-(O-di-tert-butylsilanediyl)guanosine (1360744-39-3) + 4,4'-dimethoxytrityl chloride (40615-36-9) + isobutyryl chloride (79-30-1) → N2-isobutyryl-2'-O-(N,N'-di-Boc-guanidinopropyl)-5'-O-(4,4'-dimethoxytrityl)-guanosine (1360744-43-9) + N2-isobutyryl-2'-O-(N,N'-di-Boc-N'-isobutyryl-guanidinopropyl)-5'-O-(4,4'-dimethoxytrityl)-guanosine (1360744-44-0)

Guidance literature:

2'-O-(3-(N,N'-di-tert-butoxycarbonylguanidino)propyl)-3',5'-(O-di-tert-butylsilanediyl)guanosine; isobutyryl chloride; With pyridine; at 0 - 20 ℃; for 2h;

With triethylamine tris(hydrogen fluoride); triethylamine; In tetrahydrofuran; at 20 ℃; for 1h;

4,4'-dimethoxytrityl chloride; Further stages;

DOI:10.1016/j.bmc.2011.12.024

Reference yield:

O6-(2,4,6-triisopropylbenzenesulfonyl)-3',5'-O-(di-tert-butylsilanediyl)guanosine (1207452-07-0) → N2-isobutyryl-2'-O-(N,N'-di-Boc-guanidinopropyl)-5'-O-(4,4'-dimethoxytrityl)-guanosine (1360744-43-9) + N2-isobutyryl-2'-O-(N,N'-di-Boc-N'-isobutyryl-guanidinopropyl)-5'-O-(4,4'-dimethoxytrityl)-guanosine (1360744-44-0)

Guidance literature:

Multi-step reaction with 5 steps

1.1: caesium carbonate / tert-butyl alcohol / 4 h / 20 °C

2.1: formic acid / 1,4-dioxane; water / 1 h / 20 °C

3.1: ammonia; hydrogen / methanol / 1 h / 20 °C / 22502.3 Torr / Autoclave

4.1: triethylamine / dichloromethane / 1 h / 20 °C / Cooling with ice

5.1: pyridine / 2 h / 0 - 20 °C

5.2: 1 h / 20 °C

With pyridine; formic acid; ammonia; hydrogen; caesium carbonate; triethylamine; In 1,4-dioxane; methanol; dichloromethane; water; tert-butyl alcohol;

DOI:10.1016/j.bmc.2011.12.024

Reference yield:

2'-O-(2-cyanoethyl)-3',5'-O-(di-tert-butylsilanediyl)-guanosine (1360744-37-1) → N2-isobutyryl-2'-O-(N,N'-di-Boc-guanidinopropyl)-5'-O-(4,4'-dimethoxytrityl)-guanosine (1360744-43-9) + N2-isobutyryl-2'-O-(N,N'-di-Boc-N'-isobutyryl-guanidinopropyl)-5'-O-(4,4'-dimethoxytrityl)-guanosine (1360744-44-0)

Guidance literature:

Multi-step reaction with 3 steps

1.1: ammonia; hydrogen / methanol / 1 h / 20 °C / 22502.3 Torr / Autoclave

2.1: triethylamine / dichloromethane / 1 h / 20 °C / Cooling with ice

3.1: pyridine / 2 h / 0 - 20 °C

3.2: 1 h / 20 °C

With pyridine; ammonia; hydrogen; triethylamine; In methanol; dichloromethane;

DOI:10.1016/j.bmc.2011.12.024

upstream raw materials:

O⁶-(2,4,6-triisopropylbenzenesulfonyl)-3',5'-O-(di-tert-butylsilanediyl)guanosine

2'-O-(2-cyanoethyl)-3',5'-O-(di-tert-butylsilanediyl)-guanosine

2'-O-(2-aminopropyl)-3',5'-O-(di-tert-butylsilanediyl)-guanosine

2'-O-(3-(N,N'-di-tert-butoxycarbonylguanidino)propyl)-3',5'-(O-di-tert-butylsilanediyl)guanosine

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