HCID 15157474, compound → HCID 15157475, compound

HRID 2371648Notes

Reaction equation

HRID 2371648 reaction equation
[OH:1][CH:2](CO)[CH2:3][CH2:4][CH2:5][C:6]1([CH2:35][CH2:36][CH2:37][CH:38]([OH:41])CO)[CH2:11][C:10](=[O:12])[C:9]2[CH:13]=[CH:14][C:15]([O:20][CH2:21][CH2:22][CH2:23][O:24][C:25]3[C:34]4[CH2:33][CH2:32][CH2:31][CH2:30][C:29]=4[CH:28]=[CH:27][CH:26]=3)=[C:16]([CH2:17][CH2:18][CH3:19])[C:8]=2[O:7]1.I([O-])(=O)(=O)=O.[Na+]>C(O)(C)(C)C.O>[O:12]=[C:10]1[C:9]2[CH:13]=[CH:14][C:15]([O:20][CH2:21][CH2:22][CH2:23][O:24][C:25]3[C:34]4[CH2:33][CH2:32][CH2:31][CH2:30][C:29]=4[CH:28]=[CH:27][CH:26]=3)=[C:16]([CH2:17][CH2:18][CH3:19])[C:8]=2[O:7][C:6]([CH2:35][CH2:36][CH2:37][CH:38]=[O:41])([CH2:5][CH2:4][CH2:3][CH:2]=[O:1])[CH2:11]1

Participants

5

Reactant 2

HCID 15157474HCID 15157474, compoundHCID 23667635Sodium periodate

Product 1

HCID 15157475HCID 15157475, compoundYield 60.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6386tert-ButanolSolvent

Procedure

To a solution of 200 mg (0.350 mmol) of the title product of Example 71 in 9.8 ml of t-butanol was added with stirring a solution of 300 mg (1.40 mmol) of sodium periodate in 2.2 ml of water. After two hours, the mixture was partitioned between diethyl ether and water. The organic layer was washed with brine, dried over sodium sulfate, filtered, and the solvent removed under reduced pressure. The residue was chromatographed on a silica gel column, using ethyl acetate/hexane as eluent. Crystallization from diethyl ether/hexane gave 114 mg of the title compound, m.p. 72°-73° C.

Workup

  1. customthe mixture was partitioned between diethyl ether and water
  2. washThe organic layer was washed with brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. customthe solvent removed under reduced pressure
  6. customThe residue was chromatographed on a silica gel column
  7. customCrystallization from diethyl ether/hexane

Sources & evidence

ORD record
ord-37901b160365492aadf263debdfe0171
Source dataset
uspto-grants-1992_03
Patent number
US05093353

Reaction notes

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