5'-O-(4,4-dimethoxytriphenylmethyl)-N²-phenylacetyl-2'-deoxy-6-(2,4-dinitrophenyl)thioguanosine-3'-O-(2-cyanoethyl-N,N-diisopropylamino)-phosphoramidite

Base Information

• Chemical Name: 5'-O-(4,4-dimethoxytriphenylmethyl)-N²-phenylacetyl-2'-deoxy-6-(2,4-dinitrophenyl)thioguanosine-3'-O-(2-cyanoethyl-N,N-diisopropylamino)-phosphoramidite
• CAS No.: 141076-12-2
• Molecular Formula: C₅₄H₅₆N₉O₁₁PS
• Molecular Weight: 1070.13

Synonyms:

Chemical Property of 5'-O-(4,4-dimethoxytriphenylmethyl)-N²-phenylacetyl-2'-deoxy-6-(2,4-dinitrophenyl)thioguanosine-3'-O-(2-cyanoethyl-N,N-diisopropylamino)-phosphoramidite

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Technology Process of 5'-O-(4,4-dimethoxytriphenylmethyl)-N²-phenylacetyl-2'-deoxy-6-(2,4-dinitrophenyl)thioguanosine-3'-O-(2-cyanoethyl-N,N-diisopropylamino)-phosphoramidite

There total 7 articles about 5'-O-(4,4-dimethoxytriphenylmethyl)-N²-phenylacetyl-2'-deoxy-6-(2,4-dinitrophenyl)thioguanosine-3'-O-(2-cyanoethyl-N,N-diisopropylamino)-phosphoramidite 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:

N2-phenylacetyl-2'-deoxy-6-thioguanosine (869355-10-2) → 5'-O-(4,4-dimethoxytriphenylmethyl)-N2-phenylacetyl-2'-deoxy-6-(2,4-dinitrophenyl)thioguanosine-3'-O-(2-cyanoethyl-N,N-diisopropylamino)-phosphoramidite (141076-12-2)

Guidance literature:

Multi-step reaction with 3 steps

1: Et₃N / acetonitrile

2: pyridine

3: N,N-diisopropylethyl amine / tetrahydrofuran / 1) ice-bath, 10 min., 2) RT

With pyridine; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; acetonitrile;

DOI:10.1016/S0040-4020(01)88731-7

Reference yield:

3',5'-diacetyl-N2-phenylacetyl-2'-deoxyguanosine (99519-11-6) → 5'-O-(4,4-dimethoxytriphenylmethyl)-N2-phenylacetyl-2'-deoxy-6-(2,4-dinitrophenyl)thioguanosine-3'-O-(2-cyanoethyl-N,N-diisopropylamino)-phosphoramidite (141076-12-2)

Guidance literature:

Multi-step reaction with 7 steps

1: Et₃N, 4-(dimethylamino)pyridine / CH₂Cl₂ / 1 h / Ambient temperature

2: CH₂Cl₂ / 1) ice-bath, 30 min, 2) RT, 30 min.

3: thiolacetic acid / CH₂Cl₂ / 1 h

4: 2M NaOH

5: Et₃N / acetonitrile

6: pyridine

7: N,N-diisopropylethyl amine / tetrahydrofuran / 1) ice-bath, 10 min., 2) RT

With pyridine; dmap; sodium hydroxide; triethylamine; N-ethyl-N,N-diisopropylamine; tiolacetic acid; In tetrahydrofuran; dichloromethane; acetonitrile;

DOI:10.1016/S0040-4020(01)88731-7

Reference yield:

3',5'-diacetyl-N2-phenylacetyl-2'-deoxy-6-thioguanosine (141076-15-5) → 5'-O-(4,4-dimethoxytriphenylmethyl)-N2-phenylacetyl-2'-deoxy-6-(2,4-dinitrophenyl)thioguanosine-3'-O-(2-cyanoethyl-N,N-diisopropylamino)-phosphoramidite (141076-12-2)

Guidance literature:

Multi-step reaction with 4 steps

1: 2M NaOH

2: Et₃N / acetonitrile

3: pyridine

4: N,N-diisopropylethyl amine / tetrahydrofuran / 1) ice-bath, 10 min., 2) RT

With pyridine; sodium hydroxide; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; acetonitrile;

DOI:10.1016/S0040-4020(01)88731-7

upstream raw materials:

2-cyanoethyl-N,N-(diisopropylamino)chlorophosphine

N-[9-{(2R,4S,5R)-5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-hydroxy-tetrahydro-furan-2-yl}-6-(2,4-dinitro-phenylsulfanyl)-9H-purin-2-yl]-2-phenyl-acetamide

N²-phenylacetyl-2'-deoxy-6-thioguanosine

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

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