Triacetoxyperiodinane → HCID 59235323, compound

HRID 2174334Notes

Reaction equation

HRID 2174334 reaction equation
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[Cl:23][C:24]1[C:25]([CH2:71][C:72]2[CH:77]=[CH:76][C:75]([CH2:78][CH3:79])=[CH:74][CH:73]=2)=[CH:26][C:27]([C@H:32]2[C@H:37]([O:38][CH2:39][C:40]3[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=3)[C@@H:36]([O:46][CH2:47][C:48]3[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=3)[C@H:35]([O:54][CH2:55][C:56]3[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=3)[C@@H:34]([CH2:62][O:63][CH2:64][C:65]3[CH:70]=[CH:69][CH:68]=[CH:67][CH:66]=3)[O:33]2)=[C:28]([CH2:30][OH:31])[CH:29]=1>ClCCl>[Cl:23][C:24]1[C:25]([CH2:71][C:72]2[CH:73]=[CH:74][C:75]([CH2:78][CH3:79])=[CH:76][CH:77]=2)=[CH:26][C:27]([C@H:32]2[C@H:37]([O:38][CH2:39][C:40]3[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=3)[C@@H:36]([O:46][CH2:47][C:48]3[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=3)[C@H:35]([O:54][CH2:55][C:56]3[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=3)[C@@H:34]([CH2:62][O:63][CH2:64][C:65]3[CH:66]=[CH:67][CH:68]=[CH:69][CH:70]=3)[O:33]2)=[C:28]([CH:29]=1)[CH:30]=[O:31]

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 59557721HCID 59557721, compound

Product 1

HCID 59235323HCID 59235323, compoundYield 49.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

To a cold (0° C.) stirred suspension of Dess-Martin periodinane (1.24 g, 2.92 mmol) in dichloromethane (20 mL) was added (5-chloro-4-(4-ethylbenzyl)-2-((2S,3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran-2-yl)phenyl)methanol (1.76 g, 2.25 mmol) (prepared as described in U.S. Ser. No. 12/060,767) in dichloromethane (3 mL). The mixture was stirred for 2 hours at 0° C., and the reaction was quenched with 2N sodium hydroxide (5 mL). The organic phase was separated, and the aqueous phase was extracted with ethyl acetate. The organic phases were combined, washed with saturated sodium bicarbonate, then with water and then with brine, and then dried over anhydrous sodium sulfate. The combined filtrate was concentrated under reduced pressure. The residue was purified by column chromatography to give 0.87 g of white solid. MS ESI+ (m/z): 798 (M+18)+.

Workup

  1. customprepared
  2. stirringThe mixture was stirred for 2 hours at 0° C.
  3. customthe reaction was quenched with 2N sodium hydroxide (5 mL)
  4. customThe organic phase was separated
  5. extractionthe aqueous phase was extracted with ethyl acetate
  6. washwashed with saturated sodium bicarbonate
  7. dry with materialwith water and then with brine, and then dried over anhydrous sodium sulfate
  8. concentrationThe combined filtrate was concentrated under reduced pressure
  9. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-845f026f8f6849a39c29386b1f1e4f14
Source dataset
uspto-grants-2015_06
Patent number
US09061060B2

Reaction notes

Loading…