Sodium periodate → HCID 69657893, compound

HRID 585053Notes

Reaction equation

HRID 585053 reaction equation
[C:1]([O:5][C:6](=[O:31])[NH:7][C:8]1[C:17]([CH2:18][CH2:19][CH:20]=C)=[C:16]2[C:11]([CH2:12][CH2:13][C@@H:14]([C:22](C)(C)[O:23][SiH2]C(C)(C)C)[O:15]2)=[CH:10][CH:9]=1)([CH3:4])([CH3:3])[CH3:2].I([O-])(=O)(=O)=[O:33].[Na+]>O1CCCC1.O.C(OCC)(=O)C.[Os](=O)(=O)(=O)=O>[C:1]([O:5][C:6]([N:7]1[C:8]2[C:17](=[C:16]3[C:11](=[CH:10][CH:9]=2)[CH2:12][CH2:13][C@@H:14]([CH2:22][OH:23])[O:15]3)[CH2:18][CH2:19][CH:20]1[OH:33])=[O:31])([CH3:3])([CH3:4])[CH3:2]

Participants

7

Reactant 2

HCID 23667635Sodium periodateHCID 131724978HCID 131724978, compound

Product 1

HCID 69657893HCID 69657893, compoundYield 76.6%

Reagents, catalysts & solvents 4

HCID 30318Osmium TetroxideCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (2S)-[8-but-3-enyl-2-(tert-butyl-dimethyl-silanyloxymethyl)-chroman-7-yl]-carbamic acid tert-butyl ester (0.33 g, 0.74 mmole) in anhydrous tetrahydrofuran (15 mL) and water (3 mL) at 0° C. was added osmium tetroxide (0.1 mL, 5% in water), followed by sodium periodate (0.47 g, 2.2 mmole). The mixture was stirred for 48 hours. The solution was diluted with ethyl acetate and the organic layer was washed with water, dried over Na2SO4, filtered, and the solvent evaporated in vacuum. Column chromatography on silica gel (80% ethyl acetate/hexane) afforded 0.19 g (76%) of the title compound as an oil, the t-butyldimethylsilyl protecting group having been cleaved in the course of the reaction. [α]25D=+40.66° (c=7.7, DMSO)

Workup

  1. washthe organic layer was washed with water
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. customthe solvent evaporated in vacuum

Sources & evidence

ORD record
ord-f368c6cedea64153bc03f119775654b5
Source dataset
uspto-grants-2005_08
Patent number
US06930109B2

Reaction notes

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