HCID 15157470, compound → HCID 15157471, compound

HRID 2371644Notes

Reaction equation

HRID 2371644 reaction equation
[OH:1][CH:2](CO)[CH2:3][CH2:4][C:5]1([CH2:34][CH2:35][CH:36]([OH:39])CO)[CH2:10][C:9](=[O:11])[C:8]2[CH:12]=[CH:13][C:14]([O:19][CH2:20][CH2:21][CH2:22][O:23][C:24]3[C:33]4[CH2:32][CH2:31][CH2:30][CH2:29][C:28]=4[CH:27]=[CH:26][CH:25]=3)=[C:15]([CH2:16][CH2:17][CH3:18])[C:7]=2[O:6]1.I([O-])(=O)(=O)=O.[Na+]>C(O)(C)(C)C.O>[O:11]=[C:9]1[C:8]2[CH:12]=[CH:13][C:14]([O:19][CH2:20][CH2:21][CH2:22][O:23][C:24]3[C:33]4[CH2:32][CH2:31][CH2:30][CH2:29][C:28]=4[CH:27]=[CH:26][CH:25]=3)=[C:15]([CH2:16][CH2:17][CH3:18])[C:7]=2[O:6][C:5]([CH2:4][CH2:3][CH:2]=[O:1])([CH2:34][CH2:35][CH:36]=[O:39])[CH2:10]1

Participants

5

Reactant 2

HCID 15157470HCID 15157470, compoundHCID 23667635Sodium periodate

Product 1

HCID 15157471HCID 15157471, compoundYield 76.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6386tert-ButanolSolvent

Procedure

To a solution of 90 mg (0.158 mmol) of the title product of Example 66 in 3.7 ml of t-butanol was added a solution of 135 mg (0.629 mmol) of sodium periodate in 1.0 ml of H2O. After stirring at room temperature for 2 hours, the mixture was partitioned between diethyl ether and water and the aqueous layer extracted with a fresh portion of ether. The combined organic extracts were washed with brine, dried over magnesium sulfate, filtered, and the solvent removed under reduced pressure. The residue was triturated with diethyl ether to give the title compound (61 mg), m.p. 107°-108° C.

Workup

  1. customthe mixture was partitioned between diethyl ether and water
  2. extractionthe aqueous layer extracted with a fresh portion of ether
  3. washThe combined organic extracts were washed with brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customthe solvent removed under reduced pressure
  7. customThe residue was triturated with diethyl ether

Sources & evidence

ORD record
ord-e12ac15621ac43cf9d09a4307e97a974
Source dataset
uspto-grants-1992_03
Patent number
US05093353

Reaction notes

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