2-Methylbenzenesulfonic acid → (4R,6S)-4-(tert-butyldimethylsilyloxy)-6-(dimethoxymethyl)-tetrahydropyran-2-one

HRID 1928680Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1928680
[Si:1]([O:8][C@@H:9]1[CH2:14][C@@H:13](C(O)O)[O:12][C:11](=[O:18])[CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C1(C)C(S(O)(=O)=O)=CC=CC=1.[CH:30]([O:35][CH3:36])([O:33][CH3:34])OC.C([O-])(O)=O.[Na+]>ClCCl>[Si:1]([O:8][C@@H:9]1[CH2:14][C@@H:13]([CH:30]([O:33][CH3:34])[O:35][CH3:36])[O:12][C:11](=[O:18])[CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Komponenten

6

Edukt 4

HCID 69252-Methylbenzenesulfonic acidHCID 9005Trimethyl orthoformateHCID 516892Sodium BicarbonateHCID 44128178(4R,6S)-4-(tert-butyldimethylsilyloxy)-6-(dihydroxymethyl)-tetrahydropyran-2-one

Produkt 1

HCID 68898127(4R,6S)-4-(tert-butyldimethylsilyloxy)-6-(dimethoxymethyl)-tetrahydropyran-2-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

To a solution of 1.0 g of (4R,6S)-4-(tert-butyldimethylsilyloxy)-6-(dihydroxymethyl)-tetrahydropyran-2-one (V′) in 100 mL of dichloromethane, 50 mg of toluenesulfonic acid and 4.5 mL of trimethyl orthoformate are added. After 2 hours of stirring at 25° C., 0.2 g of NaHCO3 is added and dichloromethane is distilled off. The residue is flash chromatographed (MTBE/hexane 1/1) and the solvents are distilled off to get the title compound.

Aufarbeitung

  1. distillationdichloromethane is distilled off
  2. customchromatographed (MTBE/hexane 1/1)
  3. distillationthe solvents are distilled off

Quellen und Nachweise

ORD-Eintrag
ord-2b9c94e5ab5b4cbdbbbae93991388f17
Quelldatensatz
uspto-grants-2012_05
Patentnummer
US08183397B2

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