N²-phenoxyacetyl-3',5'-O-(tetraisopropyldisiloxane-1,3-diyl)-2'-O-(2-cyanoethoxymethyl)guanosine

Base Information

• Chemical Name: N²-phenoxyacetyl-3',5'-O-(tetraisopropyldisiloxane-1,3-diyl)-2'-O-(2-cyanoethoxymethyl)guanosine
• CAS No.: 877774-46-4
• Molecular Formula: C₃₄H₅₀N₆O₉Si₂
• Molecular Weight: 742.977

Synonyms:N²-phenoxyacetyl-3',5'-O-(tetraisopropyldisiloxane-1,3-diyl)-2'-O-(2-cyanoethoxymethyl)guanosine

Chemical Property of N²-phenoxyacetyl-3',5'-O-(tetraisopropyldisiloxane-1,3-diyl)-2'-O-(2-cyanoethoxymethyl)guanosine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N²-phenoxyacetyl-3',5'-O-(tetraisopropyldisiloxane-1,3-diyl)-2'-O-(2-cyanoethoxymethyl)guanosine

There total 1 articles about N²-phenoxyacetyl-3',5'-O-(tetraisopropyldisiloxane-1,3-diyl)-2'-O-(2-cyanoethoxymethyl)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: 89.0%

3-((methylthio)methoxy)propanenitrile (877774-36-2) + N2-phenoxyacetyl-3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)guanosine (131474-72-1) → N2-phenoxyacetyl-3',5'-O-(tetraisopropyldisiloxane-1,3-diyl)-2'-O-(2-cyanoethoxymethyl)guanosine (877774-46-4)

Guidance literature:

3-((methylthio)methoxy)propanenitrile; N²-phenoxyacetyl-3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)guanosine; In tetrahydrofuran; at -45 ℃; for 0.166667h; Molecular sieve;

With N-iodo-succinimide; trifluorormethanesulfonic acid; In tetrahydrofuran; for 0.25h;

With water; sodium hydrogencarbonate; In tetrahydrofuran;

Reference yield: 99.0%

N2-phenoxyacetyl-3',5'-O-(tetraisopropyldisiloxane-1,3-diyl)-2'-O-(2-cyanoethoxymethyl)guanosine (877774-46-4) → N2-phenoxyacetyl-2'-O-(2-cyanoethoxymethyl)guanosine (877774-45-3)

Guidance literature:

With tetrabutyl ammonium fluoride; acetic acid; In tetrahydrofuran; at 20 ℃; for 1h; Product distribution / selectivity;

Reference yield:

N2-phenoxyacetyl-3',5'-O-(tetraisopropyldisiloxane-1,3-diyl)-2'-O-(2-cyanoethoxymethyl)guanosine (877774-46-4) → O6-cyanoethyl-N2-phenoxyacetyl-5′-O-(4,4′-dimethoxytrityl)-2′-O-(2-cyanoethoxymethyl)guanosine (1333502-04-7)

Guidance literature:

Multi-step reaction with 4 steps

1.1: dmap; triethylamine / dichloromethane / 0.5 h / 20 °C / Inert atmosphere

2.1: 1-Methylpyrrolidine / dichloromethane / 0.67 h / 0 °C / Inert atmosphere

2.2: 0.42 h / 0 °C / Inert atmosphere

3.1: triethylamine tris(hydrogen fluoride) / tetrahydrofuran / 2 h / 35 °C / Inert atmosphere

4.1: pyridine / 9 h / 20 °C / Inert atmosphere

With 1-Methylpyrrolidine; pyridine; dmap; triethylamine tris(hydrogen fluoride); triethylamine; In tetrahydrofuran; dichloromethane;

DOI:10.1021/jo301052v

upstream raw materials:

3-((methylthio)methoxy)propanenitrile

N²-phenoxyacetyl-3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)guanosine

Downstream raw materials:

N₂-phenoxyacetyl-2'-O-(2-cyanoethoxymethyl)guanosine

C₅₇H₅₇N₈O₁₁P

O⁶-cyanoethyl-N²-phenoxyacetyl-5′-O-(4,4′-dimethoxytrityl)-2′-O-(2-cyanoethoxymethyl)guanosine

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