Reaction #1095839

ord-93cccda84f2e4d168072888755608119

Reaction equation

CC(=O)O[C@H]1C[C@]2(C)[C@@H](O)C[C@H]3OC[C@@]3(OC(C)=O)[C@H]2[C@H](OC(=O)c2ccccc2)[C@]2(O)C[C@H](OC(=O)[C@H](O)[C@@H](NC(=O)c3ccccc3)c3ccccc3)C(C)=C1C2(C)C
9-deoxotaxol
CS(C)=O
dimethylsulfoxide
→
CC(=O)O[C@H]1C(=O)[C@@]2(C)[C@H]([C@H](OC(=O)c3ccccc3)[C@]3(O)C[C@H](OC(=O)[C@H](O)[C@@H](NC(=O)c4ccccc4)c4ccccc4)C(C)=C1C3(C)C)[C@]1(OC(C)=O)CO[C@@H]1C[C@@H]2O
Paclitaxel

Reactants

—
10-desacetoxy-7-deoxy-9-deoxotaxol
CC(=O)O[C@H]1C[C@]2(C)[C@@H](O)C[C@H]3OC[C@@]3(OC(C)=O)[C@H]2[C@H](OC(=O)c2ccccc2)[C@]2(O)C[C@H](OC(=O)[C@H](O)[C@@H](NC(=O)c3ccccc3)c3ccccc3)C(C)=C1C2(C)C
9-deoxotaxol
CS(C)=O
dimethylsulfoxide
—
7-deoxy-9-deoxotaxol

Reagents

None

Solvents

C1CCOC1
tetrahydrofuran

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    OtherThe device is then removed
  2. 2
    Otherthe coating is then partially dried at room temperature for 3 to 5 minutes
  3. 3
    Otherthe polymerization reaction
  4. 4
    OtherAn echogenic coating is formed

Procedure

A coated stent from Example 9 is dipped into a DESMODUR solution (50:50 mixture of dimethylsulfoxide and tetrahydrofuran). The device is then removed and the coating is then partially dried at room temperature for 3 to 5 minutes. The device is then immersed in a beaker of water (room temperature) for 3-5 minutes to cause the polymerization reaction to occur rapidly. An echogenic coating is formed. In addition to 9-deoxotaxol, the following are exemplary compounds that may be used to coat the device: 7-deoxy-9-deoxotaxol and 10-desacetoxy-7-deoxy-9-deoxotaxol.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: USH0002260H1uspto-grants-2011_07