N⁴-acetyl-1-[2-acetyloxymethyl-2-deoxy-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-acetyloxymethyl-2-deoxy-2-phenylseleno-3,5-O-(1,1,3,3-tetraisopropyldisioxane-1,3-diyl)-4-thio-β-D-ribofuranosyl]cytosine
• CAS No.: 753007-76-0
• Molecular Formula: C₃₂H₄₉N₃O₇SSeSi₂
• Molecular Weight: 754.954

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

Chemical Property:

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

There total 6 articles about N⁴-acetyl-1-[2-acetyloxymethyl-2-deoxy-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: 92.0%

Phenylselenyl chloride (5707-04-0) + bis-N,O-trimethylsilyl-N4-acetylcytosine + 2-acetyloxymethyl-1,4-anhydro-2-deoxy-3,5-O-(1,1,3,3-tetraisopropyldisioxane-1,3-diyl)-4-thio-D-erythro-pento-1-enitol (753007-71-5) → N4-acetyl-1-[2-acetyloxymethyl-2-deoxy-2-phenylseleno-3,5-O-(1,1,3,3-tetraisopropyldisioxane-1,3-diyl)-4-thio-β-D-ribofuranosyl]cytosine (753007-76-0)

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-acetyloxymethyl-2-deoxy-2-phenylseleno-3,5-O-(1,1,3,3-tetraisopropyldisioxane-1,3-diyl)-4-thio-β-D-ribofuranosyl]cytosine (753007-76-0)

Guidance literature:

Multi-step reaction with 5 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: tetrahydrofuran / 0.5 h / -70 °C

2.3: 85 percent / NaBH₄ / tetrahydrofuran; methanol / 0.17 h / 0 °C

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

4.1: 580.2 mg / i-Pr₂NEt; DMAP / CH₂Cl₂

5.1: 92 percent / acetonitrile / 0 °C

With dmap; 2,2,6,6-tetramethylpiperidinyl-lithium; ammonia; sodium; N-ethyl-N,N-diisopropylamine; lithium diisopropyl amide; In tetrahydrofuran; diethyl ether; dichloromethane; 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-acetyloxymethyl-2-deoxy-2-phenylseleno-3,5-O-(1,1,3,3-tetraisopropyldisioxane-1,3-diyl)-4-thio-β-D-ribofuranosyl]cytosine (753007-76-0)

Guidance literature:

Multi-step reaction with 4 steps

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

1.2: tetrahydrofuran / 0.5 h / -70 °C

1.3: 85 percent / NaBH₄ / tetrahydrofuran; methanol / 0.17 h / 0 °C

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

3.1: 580.2 mg / i-Pr₂NEt; DMAP / CH₂Cl₂

4.1: 92 percent / acetonitrile / 0 °C

With dmap; 2,2,6,6-tetramethylpiperidinyl-lithium; ammonia; sodium; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; diethyl ether; dichloromethane; acetonitrile;

DOI:10.1021/ol040035u

upstream raw materials:

Phenylselenyl chloride

2-acetyloxymethyl-1,4-anhydro-2-deoxy-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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