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

Base Information

• Chemical Name: (+)-N³-benzoyl-5-chloro-1-[2-azido-2-deoxy-3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-4-seleno-D-arabinofuranosyl]uracil
• CAS No.: 1620879-34-6
• Molecular Formula: C₂₈H₄₀ClN₅O₆SeSi₂
• Molecular Weight: 713.24

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

Chemical Property of (+)-N³-benzoyl-5-chloro-1-[2-azido-2-deoxy-3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-4-seleno-D-arabinofuranosyl]uracil

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (+)-N³-benzoyl-5-chloro-1-[2-azido-2-deoxy-3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-4-seleno-D-arabinofuranosyl]uracil

There total 13 articles about (+)-N³-benzoyl-5-chloro-1-[2-azido-2-deoxy-3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-4-seleno-D-arabinofuranosyl]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: 37.0%

(+)-N3-benzoyl-5-chloro-1-[3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-4-seleno-D-ribofuranosyl]uracil (1620879-28-8) → (+)-N3-benzoyl-5-chloro-1-[2-azido-2-deoxy-3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-4-seleno-D-arabinofuranosyl]uracil (1620879-34-6)

Guidance literature:

With diphenyl phosphoryl azide; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; at 0 - 20 ℃; for 4h; stereoselective reaction;

DOI:10.1016/j.ejmech.2014.06.031

Reference yield:

(-)-5-chloro-1-[5-O-(tert-butyldiphenylsilyl)-2,3-O-isopropylidene-4-seleno-D-ribofuranosyl]uracil (1620879-13-1) → (+)-N3-benzoyl-5-chloro-1-[2-azido-2-deoxy-3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-4-seleno-D-arabinofuranosyl]uracil (1620879-34-6)

Guidance literature:

Multi-step reaction with 4 steps

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

2: pyridine / 3 h / 0 - 20 °C

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

4: triphenylphosphine; diethylazodicarboxylate; diphenyl phosphoryl azide / tetrahydrofuran / 4 h / 0 - 20 °C

With pyridine; diphenyl phosphoryl azide; tetrabutylammomium bromide; triphenylphosphine; trifluoroacetic acid; diethylazodicarboxylate; In tetrahydrofuran; dichloromethane; water; 4: |Mitsunobu Displacement;

DOI:10.1016/j.ejmech.2014.06.031

Reference yield:

2,3-O-isopropylidene-D-ribonic-γ-lactone (30725-00-9) → (+)-N3-benzoyl-5-chloro-1-[2-azido-2-deoxy-3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-4-seleno-D-arabinofuranosyl]uracil (1620879-34-6)

Guidance literature:

Multi-step reaction with 12 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

12.1: triphenylphosphine; diethylazodicarboxylate; diphenyl phosphoryl azide / tetrahydrofuran / 4 h / 0 - 20 °C

With pyridine; dmap; selenium; sodium tetrahydroborate; trimethylsilyl trifluoromethanesulfonate; diphenyl phosphoryl azide; tetrabutylammomium bromide; water; triethylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; trifluoroacetic acid; potassium hydroxide; diethylazodicarboxylate; In tetrahydrofuran; methanol; dichloromethane; water; toluene; 8.2: |Pummerer Sulfoxide Rearrangement / 12.1: |Mitsunobu Displacement;

DOI:10.1016/j.ejmech.2014.06.031

upstream raw materials:

(-)-5-chloro-1-[5-O-(tert-butyldiphenylsilyl)-2,3-O-isopropylidene-4-seleno-D-ribofuranosyl]uracil

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-chloro-1-(2-azido-2-deoxy-4-seleno-D-arabinofuranosyl)uracil

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