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

Base Information

Chemical Name:(-)-N³-benzoyl-5-chloro-1-(2-azido-2-deoxy-4-seleno-D-arabinofuranosyl)uracil
CAS No.:1620879-40-4
Molecular Formula:C₁₆H₁₄ClN₅O₅Se
Molecular Weight:470.731
Hs Code.:

(-)-N<sup>3</sup>-benzoyl-5-chloro-1-(2-azido-2-deoxy-4-seleno-D-arabinofuranosyl)uracil

Synonyms:(-)-N³-benzoyl-5-chloro-1-(2-azido-2-deoxy-4-seleno-D-arabinofuranosyl)uracil

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (-)-N³-benzoyl-5-chloro-1-(2-azido-2-deoxy-4-seleno-D-arabinofuranosyl)uracil

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Technology Process of (-)-N³-benzoyl-5-chloro-1-(2-azido-2-deoxy-4-seleno-D-arabinofuranosyl)uracil

There total 13 articles about (-)-N³-benzoyl-5-chloro-1-(2-azido-2-deoxy-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: 78.0%

: 1620879-34-6
(+)-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

: 1620879-40-4
(-)-N³-benzoyl-5-chloro-1-(2-azido-2-deoxy-4-seleno-D-arabinofuranosyl)uracil

Guidance literature:: With triethylamine tris(hydrogen fluoride); triethylamine; In tetrahydrofuran; at 0 - 20 ℃; for 1h;
DOI:10.1016/j.ejmech.2014.06.031

Reference yield:

: 1620879-13-1
(-)-5-chloro-1-[5-O-(tert-butyldiphenylsilyl)-2,3-O-isopropylidene-4-seleno-D-ribofuranosyl]uracil

: 1620879-40-4
(-)-N³-benzoyl-5-chloro-1-(2-azido-2-deoxy-4-seleno-D-arabinofuranosyl)uracil

Guidance literature:: Multi-step reaction with 5 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

5: triethylamine; triethylamine tris(hydrogen fluoride) / tetrahydrofuran / 1 h / 0 - 20 °C

With pyridine; diphenyl phosphoryl azide; tetrabutylammomium bromide; triethylamine tris(hydrogen fluoride); triethylamine; triphenylphosphine; trifluoroacetic acid; diethylazodicarboxylate; In tetrahydrofuran; dichloromethane; water; 4: |Mitsunobu Displacement;
DOI:10.1016/j.ejmech.2014.06.031

Reference yield:

: 30725-00-9
2,3-O-isopropylidene-D-ribonic-γ-lactone

: 1620879-40-4
(-)-N³-benzoyl-5-chloro-1-(2-azido-2-deoxy-4-seleno-D-arabinofuranosyl)uracil

Guidance literature:: Multi-step reaction with 13 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

13.1: triethylamine; triethylamine tris(hydrogen fluoride) / tetrahydrofuran / 1 h / 0 - 20 °C

With pyridine; dmap; selenium; sodium tetrahydroborate; trimethylsilyl trifluoromethanesulfonate; diphenyl phosphoryl azide; tetrabutylammomium bromide; water; triethylamine tris(hydrogen fluoride); 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