5'-O-(4,4'-dimethoxytriphenylmethyl)-N₂-phenylacetyl-O⁶-methoxycarbonylmethyl-2'-deoxyguanosine

Base Information

• Chemical Name: 5'-O-(4,4'-dimethoxytriphenylmethyl)-N₂-phenylacetyl-O⁶-methoxycarbonylmethyl-2'-deoxyguanosine
• CAS No.: 302585-13-3
• Molecular Formula: C₄₂H₄₁N₅O₉
• Molecular Weight: 759.816

Synonyms:5'-O-(4,4'-dimethoxytriphenylmethyl)-N₂-phenylacetyl-O⁶-methoxycarbonylmethyl-2'-deoxyguanosine

Chemical Property of 5'-O-(4,4'-dimethoxytriphenylmethyl)-N₂-phenylacetyl-O⁶-methoxycarbonylmethyl-2'-deoxyguanosine

Chemical Property:

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Technology Process of 5'-O-(4,4'-dimethoxytriphenylmethyl)-N₂-phenylacetyl-O⁶-methoxycarbonylmethyl-2'-deoxyguanosine

There total 3 articles about 5'-O-(4,4'-dimethoxytriphenylmethyl)-N₂-phenylacetyl-O⁶-methoxycarbonylmethyl-2'-deoxyguanosine 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: 65.0%

4,4'-dimethoxytrityl chloride (40615-36-9) + N2-phenylacetyl-O6-methoxycarbonylmethyl-2'-deoxyguanosine (302584-95-8) → 5'-O-(4,4'-dimethoxytriphenylmethyl)-N2-phenylacetyl-O6-methoxycarbonylmethyl-2'-deoxyguanosine (302585-13-3)

Guidance literature:

With pyridine; dmap; cooling;

DOI:10.1016/S0040-4020(00)00556-1

Reference yield:

3',5'-diacetyl-N2-phenylacetyl-O6-methoxycarbonylmethyl-2'-deoxyguanosine (302584-93-6) → 5'-O-(4,4'-dimethoxytriphenylmethyl)-N2-phenylacetyl-O6-methoxycarbonylmethyl-2'-deoxyguanosine (302585-13-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 62.5 percent / triethylamine / methanol

2: 65 percent / pyridine; dimethylaminopyridine / cooling

With pyridine; dmap; triethylamine; In methanol; 1: Deacetylation / 2: Alkylation;

DOI:10.1016/S0040-4020(00)00556-1

Reference yield:

Acetic acid (2R,3S,5R)-2-acetoxymethyl-5-[2-phenylacetylamino-6-(2,4,6-trimethyl-benzenesulfonyloxy)-purin-9-yl]-tetrahydro-furan-3-yl ester; compound with 1-aza-bicyclo[2.2.2]octane → 5'-O-(4,4'-dimethoxytriphenylmethyl)-N2-phenylacetyl-O6-methoxycarbonylmethyl-2'-deoxyguanosine (302585-13-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 75 percent / 1,8-diazabicyclo(5.4.0)undec-7-ene / acetonitrile / 20 °C

2: 62.5 percent / triethylamine / methanol

3: 65 percent / pyridine; dimethylaminopyridine / cooling

With pyridine; dmap; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; In methanol; acetonitrile; 1: Substitution / 2: Deacetylation / 3: Alkylation;

DOI:10.1016/S0040-4020(00)00556-1

upstream raw materials:

4,4'-dimethoxytrityl chloride

N₂-phenylacetyl-O⁶-methoxycarbonylmethyl-2'-deoxyguanosine

3',5'-diacetyl-N₂-phenylacetyl-O⁶-methoxycarbonylmethyl-2'-deoxyguanosine

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