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

Base Information

• Chemical Name: N⁴-benzoyl-1-[3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-4-thio-β-D-ribofuranosyl]cytosine
• CAS No.: 497847-36-6
• Molecular Formula: C₂₈H₄₃N₃O₆SSi₂
• Molecular Weight: 605.903
• Mol file: 497847-36-6.mol

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

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

Chemical Property:

Purity/Quality:

97% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 3 articles about N⁴-benzoyl-1-[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: 93.0%

benzoic acid anhydride (93-97-0) + 1-[3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-4-thio-β-D-ribofuranosyl]cytosine (497847-35-5) → N4-benzoyl-1-[3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-4-thio-β-D-ribofuranosyl]cytosine (497847-36-6)

Guidance literature:

In N,N-dimethyl-formamide; at 50 ℃; for 9h;

DOI:10.1039/b204993g

Reference yield:

(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-[3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-4-thio-β-D-ribofuranosyl]cytosine (497847-36-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 67 percent / TMSOTf; Et₃N / toluene; CH₂Cl₂ / 0.25 h / 20 °C

2: 69 percent / MeNH₂ / methanol / 3 h / 20 °C

3: 93 percent / dimethylformamide / 9 h / 50 °C

With trimethylsilyl trifluoromethanesulfonate; triethylamine; methylamine; In methanol; dichloromethane; N,N-dimethyl-formamide; toluene; 1: Pummerer reaction;

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-[3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-4-thio-β-D-ribofuranosyl]cytosine (497847-36-6)

Guidance literature:

Multi-step reaction with 2 steps

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

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

With methylamine; In methanol; N,N-dimethyl-formamide;

DOI:10.1039/b204993g

upstream raw materials:

benzoic acid anhydride

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

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

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

Downstream raw materials:

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

N-{1-[(2R,3R,3aS,9aR)-3-(tert-Butyl-dimethyl-silanyloxy)-5,5,7,7-tetraisopropyl-tetrahydro-4,6,8-trioxa-1-thia-5,7-disila-cyclopentacycloocten-2-yl]-2-oxo-1,2-dihydro-pyrimidin-4-yl}-benzamide

N⁴-benzoyl-1-[2-O-(tert-butyldimethylsilyl)-3-C-(trimethylsilyl)ethynyl-4-thio-β-D-ribofuranosyl]cytosine

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