Triacetoxyperiodinane → HCID 86760335, compound

HRID 857970Notes

Reaction equation

HRID 857970 reaction equation
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[NH2:23][C:24]([O:26][C@@H:27]([C@@H:63]([CH3:68])/[CH:64]=[CH:65]\[CH:66]=[CH2:67])[C@@H:28]([CH3:62])[C@H:29]([O:54][Si:55]([C:58]([CH3:61])([CH3:60])[CH3:59])([CH3:57])[CH3:56])[C@@H:30]([CH3:53])[C:31]([N:33]([CH2:35][C@H:36]([CH3:52])[C@@H:37]([O:44][Si:45]([C:48]([CH3:51])([CH3:50])[CH3:49])([CH3:47])[CH3:46])[C@@H:38]([CH3:43])/[CH:39]=[CH:40]\[CH2:41][OH:42])[CH3:34])=[O:32])=[O:25]>C(Cl)Cl>[NH2:23][C:24]([O:26][C@@H:27]([C@@H:63]([CH3:68])/[CH:64]=[CH:65]\[CH:66]=[CH2:67])[C@@H:28]([CH3:62])[C@H:29]([O:54][Si:55]([C:58]([CH3:61])([CH3:60])[CH3:59])([CH3:56])[CH3:57])[C@@H:30]([CH3:53])[C:31]([N:33]([CH2:35][C@H:36]([CH3:52])[C@@H:37]([O:44][Si:45]([C:48]([CH3:51])([CH3:49])[CH3:50])([CH3:46])[CH3:47])[C@@H:38]([CH3:43])/[CH:39]=[CH:40]\[CH:41]=[O:42])[CH3:34])=[O:32])=[O:25]

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 86760334HCID 86760334, compound

Product 1

HCID 86760335HCID 86760335, compoundYield 75.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of Dess-Martin periodinane (199 mg, 0.47 mmol) and CH2Cl2 (4 mL) at room temperature, is added a solution of (2R,3S,4R,5S,6S,7Z)-5-[(aminocarbonyl)oxy]-3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-N-[(2S,3S,4S,5Z)-3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-7-hydroxy-2,4-dimethyl-5-heptenyl]-N,2,4,6-tetramethyl-7,9-decadienamide (200 mg, 0.29 mmol) and CH2Cl2 (1 mL). After stirring at room temperature for 1 h, the mixture is quenched by adding saturated NaHCO3 (1 mL) followed by saturated Na2S2O3 (1 mL). This mixture is then stirred at room temperature for 30 min, and then extracted with CH2Cl2 (4×10 mL). The combined organic layers are then dried (Na2SO4), concentrated in vacuo, and then chromatographed (silica gel eluted with hexane/EtOAc 90/10) to give the desired compound (150 mg, 75.2%) as a colorless glassy solid.

Workup

  1. customthe mixture is quenched
  2. additionby adding saturated NaHCO3 (1 mL)
  3. stirringThis mixture is then stirred at room temperature for 30 min
  4. extractionextracted with CH2Cl2 (4×10 mL)
  5. dry with materialThe combined organic layers are then dried (Na2SO4)
  6. concentrationconcentrated in vacuo
  7. customchromatographed
  8. wash(silica gel eluted with hexane/EtOAc 90/10)

Sources & evidence

ORD record
ord-79b25aaf38f540abb8e1ff3c433e8181
Source dataset
uspto-grants-2006_12
Patent number
US07148218B2

Reaction notes

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