Triacetoxyperiodinane → Tert-butyl (2S,3S)-1-(allyloxy)-3-(tert-butyldimethylsilyloxy)-4-oxobutan-2-ylcarbamate

HRID 20045Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 20045
[CH2:1]([O:4][CH2:5][C@H:6]([NH:18][C:19](=[O:25])[O:20][C:21]([CH3:24])([CH3:23])[CH3:22])[C@H:7]([O:10][Si:11]([C:14]([CH3:17])([CH3:16])[CH3:15])([CH3:13])[CH3:12])[CH2:8][OH:9])[CH:2]=[CH2:3].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl.CCOC(C)=O.C([O-])(O)=O.[Na+].[O-]S([O-])(=S)=O.[Na+].[Na+]>[CH2:1]([O:4][CH2:5][C@H:6]([NH:18][C:19](=[O:25])[O:20][C:21]([CH3:24])([CH3:23])[CH3:22])[C@H:7]([O:10][Si:11]([C:14]([CH3:16])([CH3:17])[CH3:15])([CH3:12])[CH3:13])[CH:8]=[O:9])[CH:2]=[CH2:3]

Komponenten

7

Edukt 2

HCID 159087TriacetoxyperiodinaneHCID 86614136Tert-butyl (2S,3S)-1-(allyloxy)-3-(tert-butyldimethylsilyloxy)-4-hydroxybutan-2-ylcarbamate

Produkt 1

HCID 86614135Tert-butyl (2S,3S)-1-(allyloxy)-3-(tert-butyldimethylsilyloxy)-4-oxobutan-2-ylcarbamate

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 6344DichloromethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittelHCID 24477Sodium ThiosulfateLösungsmittelHCID 516892Sodium BicarbonateLösungsmittel

Versuchsvorschrift

The crude material from Step 4 (0.040 g) was dissolved in CH2Cl2 (3 mL) and treated with Dess-Martin periodinane (0.07 g, 0.2 mmol). The mixture was stirred at ambient temperature for 4 h then diluted with EtOAc (10 mL), sat'd NaHCO3 (5 mL), and aqueous Na2S2O3 (5 mL). The biphasic mixture was stirred until it was colorless. The organic layer was washed with brine, dried (Na2SO4), filtered, and conc in vacuo. The crude aldehyde was used without further purification.

Aufarbeitung

  1. stirringThe biphasic mixture was stirred until it
  2. washThe organic layer was washed with brine
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. customThe crude aldehyde was used without further purification

Quellen und Nachweise

ORD-Eintrag
ord-b4ede3342f58419b9e8e391148d5fd35
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07745484B2

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