N⁴-benzoyl-5-[(benzyloxy)methyl]-2'-deoxy-3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)cytidine

Base Information

• Chemical Name: N⁴-benzoyl-5-[(benzyloxy)methyl]-2'-deoxy-3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)cytidine
• CAS No.: 304849-83-0
• Molecular Formula: C₃₆H₅₁N₃O₇Si₂
• Molecular Weight: 693.988

Synonyms:N⁴-benzoyl-5-[(benzyloxy)methyl]-2'-deoxy-3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)cytidine

Chemical Property of N⁴-benzoyl-5-[(benzyloxy)methyl]-2'-deoxy-3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)cytidine

Chemical Property:

Purity/Quality:

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• Pictogram(s):  
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Technology Process of N⁴-benzoyl-5-[(benzyloxy)methyl]-2'-deoxy-3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)cytidine

There total 9 articles about N⁴-benzoyl-5-[(benzyloxy)methyl]-2'-deoxy-3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)cytidine 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: 90.0%

benzoyl chloride (98-88-4) + 5-[(benzyloxy)methyl]-2'-deoxy-3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)cytidine (304849-82-9) → N4-benzoyl-5-[(benzyloxy)methyl]-2'-deoxy-3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)cytidine (304849-83-0)

Guidance literature:

In pyridine; at 0 - 20 ℃; for 15h;

DOI:10.1002/1522-2675(20000809)83:8<1962::AID-HLCA1962>3.0.CO;2-8

Reference yield:

1,3-Dichloro-1,1,3,3-tetraisopropyldisiloxane (69304-37-6) → N4-benzoyl-5-[(benzyloxy)methyl]-2'-deoxy-3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)cytidine (304849-83-0)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 78 percent / pyridine / 18 h / 20 °C

2.1: DMAP / acetonitrile / 18 h / 20 °C

3.1: Bu₃SnH; AIBN / toluene / 2.5 h / 80 °C

4.1: 1,2,4-1H-triazole; POCl₃; Et₃N / acetonitrile / 0.67 h / 20 °C

4.2: 87 percent / aq. NH₃ / dioxane / 0.5 h / 20 °C

5.1: 90 percent / pyridine / 15 h / 0 - 20 °C

With 1,2,4-Triazole; dmap; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; triethylamine; trichlorophosphate; In pyridine; toluene; acetonitrile; 1.1: Substitution / 2.1: Substitution / 3.1: Reduction / 4.1: Substitution / 4.2: Substitution / 5.1: Acylation;

DOI:10.1002/1522-2675(20000809)83:8<1962::AID-HLCA1962>3.0.CO;2-8

Reference yield:

2',3',5'-tri-O-acetyl-5-[(benzyloxy)methyl]uridine (13111-67-6) → N4-benzoyl-5-[(benzyloxy)methyl]-2'-deoxy-3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)cytidine (304849-83-0)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 95 percent / 2M NaOH / H₂O; tetrahydrofuran; methanol / 0.58 h / 0 °C

2.1: 78 percent / pyridine / 18 h / 20 °C

3.1: DMAP / acetonitrile / 18 h / 20 °C

4.1: Bu₃SnH; AIBN / toluene / 2.5 h / 80 °C

5.1: 1,2,4-1H-triazole; POCl₃; Et₃N / acetonitrile / 0.67 h / 20 °C

5.2: 87 percent / aq. NH₃ / dioxane / 0.5 h / 20 °C

6.1: 90 percent / pyridine / 15 h / 0 - 20 °C

With 1,2,4-Triazole; dmap; sodium hydroxide; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; triethylamine; trichlorophosphate; In tetrahydrofuran; pyridine; methanol; water; toluene; acetonitrile; 1.1: Hydrolysis / 2.1: Substitution / 3.1: Substitution / 4.1: Reduction / 5.1: Substitution / 5.2: Substitution / 6.1: Acylation;

DOI:10.1002/1522-2675(20000809)83:8<1962::AID-HLCA1962>3.0.CO;2-8

upstream raw materials:

benzoyl chloride

5-[(benzyloxy)methyl]-2'-deoxy-3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)cytidine

1,3-Dichloro-1,1,3,3-tetraisopropyldisiloxane

5-[(benzyloxy)methyl]uridine

Downstream raw materials:

N⁴-benzoyl-5-[(benzyloxy)methyl]-2'-deoxy-5'-O-(4,4'-dimethoxytrityl)cytidine

N⁴-benzoyl-5-[(benzyloxy)methyl]-2'-deoxy-5'-O-(4,4'-dimethoxytrityl)cytidine 3'-(2-cyanoethyl diisopropylphosphoramidite)

N⁴-benzoyl-5-[(benzyloxy)methyl]-2'-deoxycytidine

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