N⁴-acetyl-1-[2-deoxy-2-methyl-2-phenylseleno-3,5-O-(1,1,3,3-tetraisopropyldisioxane-1,3-diyl)-4-thio-β-D-ribofuranosyl]cytosine

Base Information

• Chemical Name: N⁴-acetyl-1-[2-deoxy-2-methyl-2-phenylseleno-3,5-O-(1,1,3,3-tetraisopropyldisioxane-1,3-diyl)-4-thio-β-D-ribofuranosyl]cytosine
• CAS No.: 753007-75-9
• Molecular Formula: C₃₀H₄₇N₃O₅SSeSi₂
• Molecular Weight: 696.917

Synonyms:N⁴-acetyl-1-[2-deoxy-2-methyl-2-phenylseleno-3,5-O-(1,1,3,3-tetraisopropyldisioxane-1,3-diyl)-4-thio-β-D-ribofuranosyl]cytosine

Chemical Property of N⁴-acetyl-1-[2-deoxy-2-methyl-2-phenylseleno-3,5-O-(1,1,3,3-tetraisopropyldisioxane-1,3-diyl)-4-thio-β-D-ribofuranosyl]cytosine

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Technology Process of N⁴-acetyl-1-[2-deoxy-2-methyl-2-phenylseleno-3,5-O-(1,1,3,3-tetraisopropyldisioxane-1,3-diyl)-4-thio-β-D-ribofuranosyl]cytosine

There total 5 articles about N⁴-acetyl-1-[2-deoxy-2-methyl-2-phenylseleno-3,5-O-(1,1,3,3-tetraisopropyldisioxane-1,3-diyl)-4-thio-β-D-ribofuranosyl]cytosine 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: 70.0%

Phenylselenyl chloride (5707-04-0) + bis-N,O-trimethylsilyl-N4-acetylcytosine + 1,4-anhydro-2-deoxy-2-methyl-3,5-O-(1,1,3,3-tetraisopropyldisioxane-1,3-diyl)-4-thio-D-erythro-pento-1-enitol (649571-01-7) → N4-acetyl-1-[2-deoxy-2-methyl-2-phenylseleno-3,5-O-(1,1,3,3-tetraisopropyldisioxane-1,3-diyl)-4-thio-β-D-ribofuranosyl]cytosine (753007-75-9)

Guidance literature:

In acetonitrile; at 0 ℃;

DOI:10.1021/ol040035u

Reference yield:

1,4-anhydro-2-deoxy-3,5-O-(1,1,3,3-tetraisopropyldisiloxan-1,3-diyl)-4-thio-D-erythro-pent-1-enitol (209048-61-3) → N4-acetyl-1-[2-deoxy-2-methyl-2-phenylseleno-3,5-O-(1,1,3,3-tetraisopropyldisioxane-1,3-diyl)-4-thio-β-D-ribofuranosyl]cytosine (753007-75-9)

Guidance literature:

Multi-step reaction with 4 steps

1.1: LDA / tetrahydrofuran / 0.5 h / -70 °C

1.2: 86 percent / PhSO₂Cl / tetrahydrofuran / 0.5 h / -70 °C

2.1: LTMP / tetrahydrofuran / 0.5 h / -70 °C

2.2: 71 percent / tetrahydrofuran / 0.5 h / -70 °C

3.1: 81 percent / liquid NH₃; Na / diethyl ether / 0.5 h / -80 °C

4.1: 70 percent / acetonitrile / 0 °C

With 2,2,6,6-tetramethylpiperidinyl-lithium; ammonia; sodium; lithium diisopropyl amide; In tetrahydrofuran; diethyl ether; acetonitrile;

DOI:10.1021/ol040035u

Reference yield:

1,4-anhydro-1-chloro-2-deoxy-3,5-O-(1,1,3,3-tetraisopropyldisioxane-1,3-diyl)-4-thio-D-erythro-pento-1-enitol (649570-99-0) → N4-acetyl-1-[2-deoxy-2-methyl-2-phenylseleno-3,5-O-(1,1,3,3-tetraisopropyldisioxane-1,3-diyl)-4-thio-β-D-ribofuranosyl]cytosine (753007-75-9)

Guidance literature:

Multi-step reaction with 3 steps

1.1: LTMP / tetrahydrofuran / 0.5 h / -70 °C

1.2: 71 percent / tetrahydrofuran / 0.5 h / -70 °C

2.1: 81 percent / liquid NH₃; Na / diethyl ether / 0.5 h / -80 °C

3.1: 70 percent / acetonitrile / 0 °C

With 2,2,6,6-tetramethylpiperidinyl-lithium; ammonia; sodium; In tetrahydrofuran; diethyl ether; acetonitrile;

DOI:10.1021/ol040035u

upstream raw materials:

Phenylselenyl chloride

1,4-anhydro-2-deoxy-2-methyl-3,5-O-(1,1,3,3-tetraisopropyldisioxane-1,3-diyl)-4-thio-D-erythro-pento-1-enitol

4-N-Acetylcytosine

1,4-anhydro-2-deoxy-3,5-O-(1,1,3,3-tetraisopropyldisiloxan-1,3-diyl)-4-thio-D-erythro-pent-1-enitol

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