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

Base Information

Chemical Name:(-)-5-iodo-1-[5-O-(tert-butyldiphenylsilyl)-2,3-O-isopropylidene-4-seleno-D-ribofuranosyl]uracil
CAS No.:1620879-15-3
Molecular Formula:C₂₈H₃₃IN₂O₅SeSi
Molecular Weight:711.53
Hs Code.:

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

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Chemical Property of (-)-5-iodo-1-[5-O-(tert-butyldiphenylsilyl)-2,3-O-isopropylidene-4-seleno-D-ribofuranosyl]uracil

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Technology Process of (-)-5-iodo-1-[5-O-(tert-butyldiphenylsilyl)-2,3-O-isopropylidene-4-seleno-D-ribofuranosyl]uracil

There total 8 articles about (-)-5-iodo-1-[5-O-(tert-butyldiphenylsilyl)-2,3-O-isopropylidene-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: 42.0%

: 1006032-31-0
C₂₄H₃₂O₄SeSi

: 696-07-1
5-iodouracil

: 1620879-15-3
(-)-5-iodo-1-[5-O-(tert-butyldiphenylsilyl)-2,3-O-isopropylidene-4-seleno-D-ribofuranosyl]uracil

Guidance literature:: 5-iodouracil; With trimethylsilyl trifluoromethanesulfonate; triethylamine; In toluene; at 20 ℃; for 1h;

C₂₄H₃₂O₄SeSi; In dichloromethane; toluene; at 0 - 20 ℃; for 15.3333h;
DOI:10.1016/j.ejmech.2014.06.031

Reference yield:

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

: 1620879-15-3
(-)-5-iodo-1-[5-O-(tert-butyldiphenylsilyl)-2,3-O-isopropylidene-4-seleno-D-ribofuranosyl]uracil

Guidance literature:: Multi-step reaction with 8 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

With dmap; selenium; sodium tetrahydroborate; trimethylsilyl trifluoromethanesulfonate; water; triethylamine; 3-chloro-benzenecarboperoxoic acid; potassium hydroxide; In tetrahydrofuran; methanol; dichloromethane; toluene; 8.2: |Pummerer Sulfoxide Rearrangement;
DOI:10.1016/j.ejmech.2014.06.031

Reference yield:

: 152006-17-2
2,3-O-isopropylidene-L-lyxono-1,4-lactone

: 1620879-15-3
(-)-5-iodo-1-[5-O-(tert-butyldiphenylsilyl)-2,3-O-isopropylidene-4-seleno-D-ribofuranosyl]uracil

Guidance literature:: Multi-step reaction with 6 steps

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

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

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

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

5.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 0.75 h / -78 °C

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

6.2: 15.33 h / 0 - 20 °C

With dmap; selenium; sodium tetrahydroborate; trimethylsilyl trifluoromethanesulfonate; triethylamine; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; methanol; dichloromethane; toluene; 6.2: |Pummerer Sulfoxide Rearrangement;
DOI:10.1016/j.ejmech.2014.06.031