Tetrabutylammonium Fluoride → (4R,6S)-6-(dimethoxymethyl)-tetrahydro-2H-pyran-2,4-diol

HRID 1928682Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1928682
[Si]([O:8][C@@H:9]1[CH2:14][C@@H:13]([CH:15]([O:18][CH3:19])[O:16][CH3:17])[O:12][CH:11]([OH:20])[CH2:10]1)(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[CH3:17][O:16][CH:15]([O:18][CH3:19])[C@H:13]1[O:12][CH:11]([OH:20])[CH2:10][C@H:9]([OH:8])[CH2:14]1

Komponenten

4

Edukt 2

HCID 2724141Tetrabutylammonium FluorideHCID 69184843(4R,6S)-4-(tert-butyldimethylsilyloxy)-6-(dimethoxymethyl)-tetrahydro-2H-pyran-2-ol

Produkt 1

HCID 25050459(4R,6S)-6-(dimethoxymethyl)-tetrahydro-2H-pyran-2,4-diol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

To a solution of 0.47 g of (4R,6S)-4-(tert-butyldimethylsilyloxy)-6-(dimethoxymethyl)-tetrahydro-2H-pyran-2-ol (I′) in 14 mL of tetrahydrofurane, tetra-n-butylammonium fluoride in 14 mL of THF is added. After 15 minutes of stirring at 25° C., the THF is distilled off. The residue is flash chromatographed (methanol). After methanol is distilled off, the title compound is obtained as an oil.

Aufarbeitung

  1. distillationthe THF is distilled off
  2. customchromatographed (methanol)
  3. distillationAfter methanol is distilled off

Quellen und Nachweise

ORD-Eintrag
ord-46cd5973c46543229719a1a3321ceea7
Quelldatensatz
uspto-grants-2012_05
Patentnummer
US08183397B2

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