2'-(tert-butyldimethylsilyl)-2-debenzoyl-4-deacetyl-7-(triethylsilyl)-5,20-deoxy-5,20-selenapaclitaxel 1,2-carbonate

Base Information

Chemical Name:2'-(tert-butyldimethylsilyl)-2-debenzoyl-4-deacetyl-7-(triethylsilyl)-5,20-deoxy-5,20-selenapaclitaxel 1,2-carbonate
CAS No.:225660-92-4
Molecular Formula:C₅₁H₇₁NO₁₂SeSi₂
Molecular Weight:1025.26
Hs Code.:

Synonyms:2'-(tert-butyldimethylsilyl)-2-debenzoyl-4-deacetyl-7-(triethylsilyl)-5,20-deoxy-5,20-selenapaclitaxel 1,2-carbonate

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Chemical Property of 2'-(tert-butyldimethylsilyl)-2-debenzoyl-4-deacetyl-7-(triethylsilyl)-5,20-deoxy-5,20-selenapaclitaxel 1,2-carbonate

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Technology Process of 2'-(tert-butyldimethylsilyl)-2-debenzoyl-4-deacetyl-7-(triethylsilyl)-5,20-deoxy-5,20-selenapaclitaxel 1,2-carbonate

There total 5 articles about 2'-(tert-butyldimethylsilyl)-2-debenzoyl-4-deacetyl-7-(triethylsilyl)-5,20-deoxy-5,20-selenapaclitaxel 1,2-carbonate 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: 67.0%

: 225660-83-3
2'-(tert-butyldimethylsilyl)-2-debenzoyl-4-deacetyl-7-(triethylsilyl)-5-α-iodo-4,20-epoxy-D-seco-paclitaxel 1,2-carbonate

: 225660-92-4
2'-(tert-butyldimethylsilyl)-2-debenzoyl-4-deacetyl-7-(triethylsilyl)-5,20-deoxy-5,20-selenapaclitaxel 1,2-carbonate

Guidance literature:: With lithium selenide; In tetrahydrofuran; at -20 - 25 ℃; for 2h;
DOI:10.1021/jo982095h

Reference yield:

: 994-30-9
triethylsilyl chloride

: 225660-92-4
2'-(tert-butyldimethylsilyl)-2-debenzoyl-4-deacetyl-7-(triethylsilyl)-5,20-deoxy-5,20-selenapaclitaxel 1,2-carbonate

Guidance literature:: Multi-step reaction with 6 steps

1: 1.) imidazole, 2.) imidazole / 1.) DMF, 60 deg C, 2 h, 2.) DMF, room temp., 1 h

2: 66 percent / Triton B / CH₂Cl₂; methanol / 2 h / -15 - -10 °C

3: 85 percent / CH₂Cl₂ / 24 h / 35 - 40 °C

4: 93 percent / Me₃SiI / CH₂Cl₂ / 0.75 h / -78 °C

5: 96 percent / DMAP, trifluoromethanesulfonyl chloride / CH₂Cl₂ / 0.83 h / Ambient temperature

6: 67 percent / Li₂Se / tetrahydrofuran / 2 h / -20 - 25 °C

With 1H-imidazole; dmap; lithium selenide; trimethylsilyl iodide; trifluoromethane sulfonyl chloride; N-benzyl-trimethylammonium hydroxide; In tetrahydrofuran; methanol; dichloromethane;
DOI:10.1021/jo982095h

Reference yield:

: 156413-61-5
2'-(tert-butyldimethylsilyl)-7-(triethylsilyl)paclitaxel

: 225660-92-4
2'-(tert-butyldimethylsilyl)-2-debenzoyl-4-deacetyl-7-(triethylsilyl)-5,20-deoxy-5,20-selenapaclitaxel 1,2-carbonate

Guidance literature:: Multi-step reaction with 5 steps

1: 66 percent / Triton B / CH₂Cl₂; methanol / 2 h / -15 - -10 °C

2: 85 percent / CH₂Cl₂ / 24 h / 35 - 40 °C

3: 93 percent / Me₃SiI / CH₂Cl₂ / 0.75 h / -78 °C

4: 96 percent / DMAP, trifluoromethanesulfonyl chloride / CH₂Cl₂ / 0.83 h / Ambient temperature

5: 67 percent / Li₂Se / tetrahydrofuran / 2 h / -20 - 25 °C

With dmap; lithium selenide; trimethylsilyl iodide; trifluoromethane sulfonyl chloride; N-benzyl-trimethylammonium hydroxide; In tetrahydrofuran; methanol; dichloromethane;
DOI:10.1021/jo982095h