Dimethyldioxirane → HCID 16195253, compound

HRID 748499Notes

Reaction equation

HRID 748499 reaction equation
CC1(C)O[O:3]1.[CH3:6][C@H:7]1[C@H:28]2[O:29][C@@H:30]3[C@@:65]([CH3:68])([CH2:66][CH2:67][C@@H:27]2[O:26][C@@H:10]2[CH2:11][C@:12]4([CH3:25])[O:18][C@@H:17]5[C:19]([CH3:24])=[CH:20][C:21]([O:23][C@H:16]5[CH2:15][C@H:13]4[O:14][C@H:9]2[CH2:8]1)=[O:22])[O:64][C@@:33]1([CH3:69])[CH2:34][C@H:35]2[O:43][C@H:42]4[CH2:44][C@H:45]5[O:51][C@@:50]6([CH3:62])[C@@H:52]([OH:61])[CH2:53][C@@H:54]([CH2:56][C:57]([CH:59]=[O:60])=[CH2:58])[O:55][C@@H:49]6[CH2:48][C@@H:46]5[O:47][C@@H:41]4[CH:40]=[CH:39][CH2:38][C@:36]2([CH3:63])[O:37][C@@H:32]1[CH2:31]3>CC(C)=O>[CH3:6][C@H:7]1[CH:28]2[O:29][CH:30]3[C@@:65]([CH3:68])([CH2:66][CH2:67][CH:27]2[O:26][CH:10]2[CH2:11][C@:12]4([CH3:25])[O:18][CH:17]5[C:19]([CH3:24])=[CH:20][C:21]([O:23][CH:16]5[CH2:15][CH:13]4[O:14][CH:9]2[CH2:8]1)=[O:22])[O:64][C@@:33]1([CH3:69])[CH2:34][CH:35]2[O:43][CH:42]4[CH2:44][CH:45]5[O:51][C@@:50]6([CH3:62])[CH:52]([OH:61])[CH2:53][CH:54]([CH2:56][C:57]([CH:59]=[O:60])=[CH2:58])[O:55][CH:49]6[CH2:48][CH:46]5[O:47][CH:41]4[CH:40]4[O:3][CH:39]4[CH2:38][C@@:36]2([CH3:63])[O:37][CH:32]1[CH2:31]3

Participants

4

Reactant 2

HCID 115197DimethyldioxiraneHCID 10865865Brevetoxin B

Product 1

HCID 16195253HCID 16195253, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Epoxidation of the C-27, C-28 Double Bond of PbTx-2 To Provide PbTx-6. Dimethyldioxirane was generated in a distillation apparatus, connected to a dry ice condenser, according to the procedure described by Adam17 for a small-scale preparation. The receiving flask was charged with PbTx-2 (2.33 mg) in 5.0 mL of acetone and was cooled in an ice/salt bath. The reaction was monitored by HPLC. When all of the PbTx-2 was consumed, the acetone was evaporated in vacuo, and the residue taken up in 1.0 mL of methanol and purified by HPLC to provide 2.25 mg (95%) of PbTx-6. DCI MS (NH3): 911 (M+1), 928 (M+NH4), 893 (M−H2O). 1H and 13C NMR were identical to that reported by Shimizu.

Workup

  1. customconnected to a dry ice condenser
  2. customdescribed by Adam17 for a small-scale preparation
  3. temperaturewas cooled in an ice/salt bath
  4. customWhen all of the PbTx-2 was consumed
  5. customthe acetone was evaporated in vacuo
  6. custompurified by HPLC

Sources & evidence

ORD record
ord-87ff382a31aa401c88b8b8773db4df4a
Source dataset
uspto-grants-2008_07
Patent number
US07399782B2

Reaction notes

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