5'-O-(4,4'-dimethoxytrityl)-3'-O-pivaloyloxymethyl-N⁶-phenoxyacetyl-adenosine

Base Information

• Chemical Name: 5'-O-(4,4'-dimethoxytrityl)-3'-O-pivaloyloxymethyl-N⁶-phenoxyacetyl-adenosine
• CAS No.: 1146634-31-2
• Molecular Formula: C₄₅H₄₇N₅O₁₀
• Molecular Weight: 817.896
• Mol file: 1146634-31-2.mol

Synonyms:5'-O-(4,4'-dimethoxytrityl)-3'-O-pivaloyloxymethyl-N⁶-phenoxyacetyl-adenosine

Chemical Property of 5'-O-(4,4'-dimethoxytrityl)-3'-O-pivaloyloxymethyl-N⁶-phenoxyacetyl-adenosine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5'-O-(4,4'-dimethoxytrityl)-3'-O-pivaloyloxymethyl-N⁶-phenoxyacetyl-adenosine

There total 2 articles about 5'-O-(4,4'-dimethoxytrityl)-3'-O-pivaloyloxymethyl-N⁶-phenoxyacetyl-adenosine 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: 34.0%

Chloromethyl pivalate (18997-19-8) + 5'-O-dimethoxytrityl-N6-phenoxyacetyladenosine (121076-16-2) → 5'-O-(4,4'-dimethoxytrityl)-2'-O-pivaloyloxymethyl-N6-phenoxyacetyl-adenosine (1097131-05-9) + 5'-O-(4,4'-dimethoxytrityl)-3'-O-pivaloyloxymethyl-N6-phenoxyacetyl-adenosine (1146634-31-2)

Guidance literature:

With tetrabutylammomium bromide; di(n-butyl)tin oxide; In 1,1-dichloroethane; at 75 ℃; for 2.5h; Microwave irradiation;

DOI:10.1002/chem.200801392

Reference yield: 30.0%

iodomethyl pivaloate (53064-79-2) + 5'-O-dimethoxytrityl-N6-phenoxyacetyladenosine (121076-16-2) → 5'-O-(4,4'-dimethoxytrityl)-2'-O-pivaloyloxymethyl-N6-phenoxyacetyl-adenosine (1097131-05-9) + 5'-O-(4,4'-dimethoxytrityl)-3'-O-pivaloyloxymethyl-N6-phenoxyacetyl-adenosine (1146634-31-2)

Guidance literature:

With tetrabutylammomium bromide; di(n-butyl)tin oxide; In 1,2-dichloro-ethane; at 70 ℃; for 1h;

DOI:10.1016/j.bmc.2013.06.008

Reference yield: 68.0%

5'-O-(4,4'-dimethoxytrityl)-3'-O-pivaloyloxymethyl-N6-phenoxyacetyl-adenosine (1146634-31-2) + 2-cyanoethyl-N,N-(diisopropylamino)chlorophosphine (124482-92-4,89992-70-1) → 5'-O-(4,4'-dimethoxytrityl)-3'-O-pivaloyloxymethyl-2'-O-(2-cyanoethyl-N,N-diisopropylphosphoramidite)-N6-phenoxyacetyl-adenosine (1450897-38-7,1450897-39-8)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20 ℃; for 2h; Inert atmosphere;

DOI:10.1016/j.bmc.2013.06.008

upstream raw materials:

Chloromethyl pivalate

5'-O-dimethoxytrityl-N₆-phenoxyacetyladenosine

iodomethyl pivaloate

Downstream raw materials:

5'-O-(4,4'-dimethoxytrityl)-3'-O-pivaloyloxymethyl-2'-O-(2-cyanoethyl-N,N-diisopropylphosphoramidite)-N⁶-phenoxyacetyl-adenosine

C₅₅H₅₅N₅O₁₅