N²-acetyl-9-[5'-O-(4,4'-dimethoxytrityl)-2'-O-(2-trifluoroacetamido)ethyl-β-D-ribofuranosyl]guanine

Base Information

• Chemical Name: N²-acetyl-9-[5'-O-(4,4'-dimethoxytrityl)-2'-O-(2-trifluoroacetamido)ethyl-β-D-ribofuranosyl]guanine
• CAS No.: 911110-88-8
• Molecular Formula: C₃₇H₃₇F₃N₆O₉
• Molecular Weight: 766.731
• Mol file: 911110-88-8.mol

Synonyms:N²-acetyl-9-[5'-O-(4,4'-dimethoxytrityl)-2'-O-(2-trifluoroacetamido)ethyl-β-D-ribofuranosyl]guanine

Chemical Property of N²-acetyl-9-[5'-O-(4,4'-dimethoxytrityl)-2'-O-(2-trifluoroacetamido)ethyl-β-D-ribofuranosyl]guanine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N²-acetyl-9-[5'-O-(4,4'-dimethoxytrityl)-2'-O-(2-trifluoroacetamido)ethyl-β-D-ribofuranosyl]guanine

There total 4 articles about N²-acetyl-9-[5'-O-(4,4'-dimethoxytrityl)-2'-O-(2-trifluoroacetamido)ethyl-β-D-ribofuranosyl]guanine 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: 32.0%

N2-acetyl-9-[3',5'-di-O-acetyl-2'-O-(2-trifluoroacetamido)ethyl-β-D-ribofuranosyl]guanine (911110-87-7) + 4,4'-dimethoxytrityl chloride (40615-36-9) → N2-acetyl-9-[5'-O-(4,4'-dimethoxytrityl)-2'-O-(2-trifluoroacetamido)ethyl-β-D-ribofuranosyl]guanine (911110-88-8)

Guidance literature:

With pyridine; at 20 ℃; for 3.5h;

DOI:10.1002/ejoc.200600182

Reference yield:

N2-acetyl-6-chloro-9-[3',5'-di-O-acetyl-2'-O-(2-trifluoroacetamido)ethyl-β-D-ribofuranosyl]purine (911110-82-2) → N2-acetyl-9-[5'-O-(4,4'-dimethoxytrityl)-2'-O-(2-trifluoroacetamido)ethyl-β-D-ribofuranosyl]guanine (911110-88-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 58 percent / cyanoethanol; Cs₂CO₃ / tetrahydrofuran / 1.5 h / 0 °C

2: 32 percent / pyridine; MS / 3.5 h / 20 °C

With pyridine; caesium carbonate; 2-hydroxy-propionitrile; In tetrahydrofuran;

DOI:10.1002/ejoc.200600182

Reference yield:

N-(6-chloro-7(9)H-purin-2-yl)-acetamide (7602-01-9) → N2-acetyl-9-[5'-O-(4,4'-dimethoxytrityl)-2'-O-(2-trifluoroacetamido)ethyl-β-D-ribofuranosyl]guanine (911110-88-8)

Guidance literature:

Multi-step reaction with 3 steps

1.1: BSA / 1,2-dichloro-ethane / 0.5 h / 80 °C

1.2: 68 percent / TMSOTf / toluene / 2.5 h / 80 °C

2.1: 58 percent / cyanoethanol; Cs₂CO₃ / tetrahydrofuran / 1.5 h / 0 °C

3.1: 32 percent / pyridine; MS / 3.5 h / 20 °C

With pyridine; benzenesulfonamide; caesium carbonate; 2-hydroxy-propionitrile; In tetrahydrofuran; 1,2-dichloro-ethane; 1.2: Vorbrueggen reaction;

DOI:10.1002/ejoc.200600182

upstream raw materials:

N²-acetyl-9-[3',5'-di-O-acetyl-2'-O-(2-trifluoroacetamido)ethyl-β-D-ribofuranosyl]guanine

4,4'-dimethoxytrityl chloride

N²-acetyl-6-chloro-9-[3',5'-di-O-acetyl-2'-O-(2-trifluoroacetamido)ethyl-β-D-ribofuranosyl]purine

N-(6-chloro-7⁽⁹⁾H-purin-2-yl)-acetamide