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

HRID 1261816Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1261816
[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-80a13d9d9c5447929913a4152c95e3a8
Quelldatensatz
uspto-grants-2013_06
Patentnummer
US08471045B2

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