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

Base Information

• Chemical Name: N⁴-benzoyl-1-[2-O-(tert-butyldimethylsilyl)-3-C-(trimethylsilyl)ethynyl-4-thio-β-D-ribofuranosyl]cytosine
• CAS No.: 497847-40-2
• Molecular Formula: C₂₇H₃₉N₃O₅SSi₂
• Molecular Weight: 573.861
• Mol file: 497847-40-2.mol

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

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

There total 9 articles about N⁴-benzoyl-1-[2-O-(tert-butyldimethylsilyl)-3-C-(trimethylsilyl)ethynyl-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: 64.0%

trimethylsilylacetylene (1066-54-2) + N-{1-[3-(tert-butyl-dimethyl-silanyloxy)-5-hydroxymethyl-4-oxo-tetrahydro-thiophen-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 (497847-40-2)

Guidance literature:

trimethylsilylacetylene; With n-butyllithium; In tetrahydrofuran; hexane; at -20 ℃; for 1h;

With cerium(III) chloride; In tetrahydrofuran; hexane; at -78 ℃; for 1h;

N-{1-[3-(tert-butyl-dimethyl-silanyloxy)-5-hydroxymethyl-4-oxo-tetrahydro-thiophen-2-yl]-2-oxo-1,2-dihydro-pyrimidin-4-yl}-benzamide; In tetrahydrofuran; hexane; at -78 ℃; for 0.5h; Further stages.;

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-[2-O-(tert-butyldimethylsilyl)-3-C-(trimethylsilyl)ethynyl-4-thio-β-D-ribofuranosyl]cytosine (497847-40-2)

Guidance literature:

Multi-step reaction with 9 steps

1.1: 67 percent / TMSOTf; Et₃N / toluene; CH₂Cl₂ / 0.25 h / 20 °C

2.1: 69 percent / MeNH₂ / methanol / 3 h / 20 °C

3.1: 93 percent / dimethylformamide / 9 h / 50 °C

4.1: 2,6-lutidine / CH₂Cl₂ / 15 h / 20 °C

5.1: 1.04 g / TBAF; AcOH / tetrahydrofuran / 2 h / 0 °C

6.1: 89 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / 0 °C

7.1: 86 percent / Ac₂O / dimethylsulfoxide / 2.5 h / 20 °C

8.1: aq. TFA / 0.33 h / 0 °C

9.1: n-BuLi / tetrahydrofuran; hexane / 1 h / -20 °C

9.2: CeCl₃ / tetrahydrofuran; hexane / 1 h / -78 °C

9.3: 64 percent / tetrahydrofuran; hexane / 0.5 h / -78 °C

With 2,6-dimethylpyridine; n-butyllithium; trimethylsilyl trifluoromethanesulfonate; tetrabutyl ammonium fluoride; acetic anhydride; acetic acid; triethylamine; methylamine; trifluoroacetic acid; In tetrahydrofuran; methanol; hexane; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene; 1.1: Pummerer reaction;

DOI:10.1039/b204993g

Reference yield:

1-[3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-4-thio-β-D-ribofuranosyl]cytosine (497847-35-5) → N4-benzoyl-1-[2-O-(tert-butyldimethylsilyl)-3-C-(trimethylsilyl)ethynyl-4-thio-β-D-ribofuranosyl]cytosine (497847-40-2)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 93 percent / dimethylformamide / 9 h / 50 °C

2.1: 2,6-lutidine / CH₂Cl₂ / 15 h / 20 °C

3.1: 1.04 g / TBAF; AcOH / tetrahydrofuran / 2 h / 0 °C

4.1: 89 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / 0 °C

5.1: 86 percent / Ac₂O / dimethylsulfoxide / 2.5 h / 20 °C

6.1: aq. TFA / 0.33 h / 0 °C

7.1: n-BuLi / tetrahydrofuran; hexane / 1 h / -20 °C

7.2: CeCl₃ / tetrahydrofuran; hexane / 1 h / -78 °C

7.3: 64 percent / tetrahydrofuran; hexane / 0.5 h / -78 °C

With 2,6-dimethylpyridine; n-butyllithium; tetrabutyl ammonium fluoride; acetic anhydride; acetic acid; trifluoroacetic acid; In tetrahydrofuran; hexane; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide;

DOI:10.1039/b204993g

upstream raw materials:

trimethylsilylacetylene

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

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

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