Sodium periodate → HCID 59444766, compound

HRID 1363851Notes

Reaction equation

HRID 1363851 reaction equation
[Si:1]([O:8][C@H:9]1[CH2:20][C:19](=[O:21])[O:18][C@H:17](/[C:22](/[CH3:47])=[CH:23]/[CH:24](O)[CH:25](O)[C@@H](C)C[C@@H]2[C@@H]([C@H](C)[C@@H](O[Si](C(C)(C)C)(C)C)CC)O2)[C@@H:16]([CH3:48])[CH:15]=[CH:14][C@@H:13]2[O:49][CH:50]([C:52]3[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=3)[O:51][C@:12]2([CH3:58])[CH2:11][CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].I([O-])(=O)(=O)=O.[Na+]>C1COCC1.O.C(OCC)(=O)C>[Si:1]([O:8][C@H:9]1[CH2:20][C:19](=[O:21])[O:18][C@H:17](/[C:22](/[CH3:47])=[CH:23]/[CH:24]=[CH2:25])[C@@H:16]([CH3:48])[CH:15]=[CH:14][C@@H:13]2[O:49][CH:50]([C:52]3[CH:53]=[CH:54][CH:55]=[CH:56][CH:57]=3)[O:51][C@:12]2([CH3:58])[CH2:11][CH2:10]1)([C:4]([CH3:5])([CH3:6])[CH3:7])([CH3:2])[CH3:3]

Participants

6

Reactant 2

HCID 23667635Sodium periodateHCID 86618045HCID 86618045, compound

Product 1

HCID 59444766HCID 59444766, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

(3aS,4E,6S,7S,11R,13aR)-11-{[tert-butyl(dimethyl)silyl]oxy}-7-{(1E,5S)-6-[(2R,3R)-3-((1S,2S)-2-{[tert-butyl(dimethyl)silyl]oxy}-1-methylbutyl)oxiran-2-yl]-3,4-dihydroxy-1,5-dimethylhex-1-en-1-yl}-6,13a-dimethyl-2-phenyl-3a,6,7,10,11,12,13,13a-octahydro-9H-[1,3]dioxolo[4,5-f]oxacyclododecin-9-one (1.46 g, 1.73 mmol) was dissolved in THF (30 ml) and water (7.5 ml), followed by addition of sodium metaperiodate (1.11 g, 5.19 mmol) at room temperature, and the mixture was stirred at the same temperature for 1.5 hours. The reaction solution was diluted with ethyl acetate and washed with distilled water and brine. After the organic layer was dried over anhydrous sodium sulfate and the drying agent was filtered off, the organic layer was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (Kanto, commercial name Silica Gel 60N, 40-100 μm; heptane:ethyl acetate=10:1→8:1→5:1) to obtain the title compound Q20 (0.485 g) as a colorless oil and to obtain the title compound P18b (0.803 g) as a colorless oil. The title compound P18b was determined to be a mixture of α benzylidene acetal and β benzylidene acetal in a ratio of 1:3.2 by 1H-NMR.

Workup

  1. washwashed with distilled water and brine
  2. dry with materialAfter the organic layer was dried over anhydrous sodium sulfate
  3. filtrationthe drying agent was filtered off
  4. concentrationthe organic layer was concentrated under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography (Kanto, commercial name Silica Gel 60N, 40-100 μm; heptane:ethyl acetate=10:1→8:1→5:1)

Sources & evidence

ORD record
ord-2f0b42023fbb4a81b3bc536674e1cc25
Source dataset
uspto-grants-2011_02
Patent number
US07884128B2

Reaction notes

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