N⁴-benzoyl-1-[2-O-(2,4-dimethoxybenzoyl)-3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-4-thio-β-D-ribofuranosyl]cytosine

Base Information

• Chemical Name: N⁴-benzoyl-1-[2-O-(2,4-dimethoxybenzoyl)-3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-4-thio-β-D-ribofuranosyl]cytosine
• CAS No.: 497847-32-2
• Molecular Formula: C₃₇H₅₁N₃O₉SSi₂
• Molecular Weight: 770.064
• Mol file: 497847-32-2.mol

Synonyms:N⁴-benzoyl-1-[2-O-(2,4-dimethoxybenzoyl)-3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-4-thio-β-D-ribofuranosyl]cytosine

Chemical Property of N⁴-benzoyl-1-[2-O-(2,4-dimethoxybenzoyl)-3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-4-thio-β-D-ribofuranosyl]cytosine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N⁴-benzoyl-1-[2-O-(2,4-dimethoxybenzoyl)-3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-4-thio-β-D-ribofuranosyl]cytosine

There total 1 articles about N⁴-benzoyl-1-[2-O-(2,4-dimethoxybenzoyl)-3,5-O-(1,1,3,3-tetraisopropyldisiloxane-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: 67.0%

4-N-benzoylcytosine (26661-13-2) + (R)-1,4-anhydro-2-O-(2,4-dimethoxybenzoyl)-3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-4-sulfinyl-D-ribitol (291758-13-9) → N4-benzoyl-1-[2-O-(2,4-dimethoxybenzoyl)-3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-4-thio-β-D-ribofuranosyl]cytosine (497847-32-2)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; triethylamine; In dichloromethane; toluene; at 20 ℃; for 0.25h;

DOI:10.1039/b204993g

Reference yield:

N4-benzoyl-1-[2-O-(2,4-dimethoxybenzoyl)-3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-4-thio-β-D-ribofuranosyl]cytosine (497847-32-2) → N4-benzoyl-1-[2-O-(tert-butyldimethylsilyl)-4-thio-β-D-ribofuranosyl]cytosine (497847-37-7)

Guidance literature:

Multi-step reaction with 4 steps

1: 69 percent / MeNH₂ / methanol / 3 h / 20 °C

2: 93 percent / dimethylformamide / 9 h / 50 °C

3: 2,6-lutidine / CH₂Cl₂ / 15 h / 20 °C

4: 1.04 g / TBAF; AcOH / tetrahydrofuran / 2 h / 0 °C

With 2,6-dimethylpyridine; tetrabutyl ammonium fluoride; acetic acid; methylamine; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1039/b204993g

Reference yield:

N4-benzoyl-1-[2-O-(2,4-dimethoxybenzoyl)-3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-4-thio-β-D-ribofuranosyl]cytosine (497847-32-2) → N4-benzoyl-1-[2,5-bis-O-(tert-butyldimethylsilyl)-4-thio-β-D-ribofuran-3-ulosyl]cytosine (497847-39-9)

Guidance literature:

Multi-step reaction with 6 steps

1: 69 percent / MeNH₂ / methanol / 3 h / 20 °C

2: 93 percent / dimethylformamide / 9 h / 50 °C

3: 2,6-lutidine / CH₂Cl₂ / 15 h / 20 °C

4: 1.04 g / TBAF; AcOH / tetrahydrofuran / 2 h / 0 °C

5: 89 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / 0 °C

6: 86 percent / Ac₂O / dimethylsulfoxide / 2.5 h / 20 °C

With 2,6-dimethylpyridine; tetrabutyl ammonium fluoride; acetic anhydride; acetic acid; methylamine; In tetrahydrofuran; methanol; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide;

DOI:10.1039/b204993g

upstream raw materials:

4-N-benzoylcytosine

(R)-1,4-anhydro-2-O-(2,4-dimethoxybenzoyl)-3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-4-sulfinyl-D-ribitol

Downstream raw materials:

N⁴-benzoyl-1-(4-thio-β-D-ribo-pentofuranosyl)cytosine

N⁴-benzoyl-1-[2-O-(tert-butyldimethylsilyl)-4-thio-β-D-ribofuranosyl]cytosine

N⁴-benzoyl-1-[2,5-bis-O-(tert-butyldimethylsilyl)-4-thio-β-D-ribofuran-3-ulosyl]cytosine

N⁴-benzoyl-1-[3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-4-thio-β-D-ribofuranosyl]cytosine