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

Base Information

• Chemical Name: 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
• CAS No.: 1054656-82-4
• Molecular Formula: C₃₄H₅₇N₃O₆SSi₃
• Molecular Weight: 720.166
• Mol file: 1054656-82-4.mol

Synonyms:

Chemical Property of 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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 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

There total 4 articles about 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 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:

t-butyldimethylsiyl triflate (69739-34-0) + N4-benzoyl-1-[3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-4-thio-β-D-ribofuranosyl]cytosine (497847-36-6) → 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 (1054656-82-4)

Guidance literature:

With 2,6-dimethylpyridine; In dichloromethane; at 20 ℃; for 15h;

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) → 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 (1054656-82-4)

Guidance literature:

Multi-step reaction with 4 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

4: 2,6-lutidine / CH₂Cl₂ / 15 h / 20 °C

With 2,6-dimethylpyridine; trimethylsilyl trifluoromethanesulfonate; triethylamine; methylamine; In methanol; dichloromethane; N,N-dimethyl-formamide; toluene; 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) → 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 (1054656-82-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 93 percent / dimethylformamide / 9 h / 50 °C

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

With 2,6-dimethylpyridine; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1039/b204993g

upstream raw materials:

t-butyldimethylsiyl triflate

N⁴-benzoyl-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

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

Downstream raw materials:

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

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

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