(-)-N³-benzoyl-5-bromo-1-[3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-4-seleno-D-ribofuranosyl]uracil

Base Information

• Chemical Name: (-)-N³-benzoyl-5-bromo-1-[3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-4-seleno-D-ribofuranosyl]uracil
• CAS No.: 1620879-29-9
• Molecular Formula: C₂₈H₄₁BrN₂O₇SeSi₂
• Molecular Weight: 732.678

Synonyms:(-)-N³-benzoyl-5-bromo-1-[3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-4-seleno-D-ribofuranosyl]uracil

Chemical Property of (-)-N³-benzoyl-5-bromo-1-[3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-4-seleno-D-ribofuranosyl]uracil

Chemical Property:

Purity/Quality:

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Technology Process of (-)-N³-benzoyl-5-bromo-1-[3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-4-seleno-D-ribofuranosyl]uracil

There total 11 articles about (-)-N³-benzoyl-5-bromo-1-[3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-4-seleno-D-ribofuranosyl]uracil 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: 43.0%

(-)-5-bromo-1-[3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-4-seleno-D-ribofuranosyl]uracil (1620879-23-3) + benzoyl chloride (98-88-4) → (-)-N3-benzoyl-5-bromo-1-[3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-4-seleno-D-ribofuranosyl]uracil (1620879-29-9)

Guidance literature:

With tetrabutylammomium bromide; In dichloromethane; at 20 ℃; for 15h;

DOI:10.1016/j.ejmech.2014.06.031

Reference yield:

(-)-1-(4-seleno-D-ribofuranosyl)-5-bromouracil (1620879-18-6) → (-)-N3-benzoyl-5-bromo-1-[3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-4-seleno-D-ribofuranosyl]uracil (1620879-29-9)

Guidance literature:

Multi-step reaction with 2 steps

1: pyridine / 3 h / 0 - 20 °C

2: tetrabutylammomium bromide / dichloromethane / 15 h / 20 °C

With pyridine; tetrabutylammomium bromide; In dichloromethane;

DOI:10.1016/j.ejmech.2014.06.031

Reference yield:

2,3-O-isopropylidene-D-ribonic-γ-lactone (30725-00-9) → (-)-N3-benzoyl-5-bromo-1-[3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-4-seleno-D-ribofuranosyl]uracil (1620879-29-9)

Guidance literature:

Multi-step reaction with 11 steps

1.1: triethylamine / dichloromethane / 2 h / -20 - 20 °C

2.1: potassium hydroxide; water / dichloromethane / 2 h / -20 - 20 °C

2.2: 15 h / 20 °C

3.1: triethylamine; dmap / dichloromethane / 3 h / 20 °C

4.1: sodium tetrahydroborate / methanol / 3 h / 0 - 20 °C

5.1: triethylamine; dmap / dichloromethane / 0.5 h / 0 °C

6.1: sodium tetrahydroborate; selenium / methanol; tetrahydrofuran / 15 h / 70 °C

7.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 0.75 h / -78 °C

8.1: triethylamine; trimethylsilyl trifluoromethanesulfonate / toluene / 1 h / 20 °C

8.2: 15.33 h / 0 - 20 °C

9.1: trifluoroacetic acid / tetrahydrofuran; water / 15 h / 0 - 20 °C

10.1: pyridine / 3 h / 0 - 20 °C

11.1: tetrabutylammomium bromide / dichloromethane / 15 h / 20 °C

With pyridine; dmap; selenium; sodium tetrahydroborate; trimethylsilyl trifluoromethanesulfonate; tetrabutylammomium bromide; water; triethylamine; 3-chloro-benzenecarboperoxoic acid; trifluoroacetic acid; potassium hydroxide; In tetrahydrofuran; methanol; dichloromethane; water; toluene; 8.2: |Pummerer Sulfoxide Rearrangement;

DOI:10.1016/j.ejmech.2014.06.031

upstream raw materials:

(-)-1-(4-seleno-D-ribofuranosyl)-5-bromouracil

2,3-O-isopropylidene-D-ribonic-γ-lactone

2,3-O-isopropylidene-L-lyxono-1,4-lactone

(3aR,6S,6aR)-6-(((tert-butyldiphenylsilyl)oxy)methyl)-2,2-dimethyldihydrofuro[3,4-d][1,3]dioxol-4(3aH)-one

Downstream raw materials:

(-)-N³-benzoyl-5-bromo-1-(2-azido-2-deoxy-4-seleno-D-arabinofuranosyl)uracil

(-)-N³-benzoyl-5-bromo-1-[2-azido-2-deoxy-3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-4-seleno-D-arabinofuranosyl]uracil

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