(2-{2-[2-((2R,3R,4R,5R,6R)-4,5-Diacetoxy-6-acetoxymethyl-3-acetylamino-tetrahydro-pyran-2-yloxy)-ethoxy]-ethoxy}-ethoxy)-acetic acid benzyl ester → N-Acetyl-D-Galactosamine

HRID 1772311Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1772311
C(OC(=O)COCCOCCOCC[O:20][C@H:21]1[C@H:26]([NH:27][C:28](=[O:30])[CH3:29])[C@@H:25]([O:31]C(=O)C)[C@@H:24]([O:35]C(=O)C)[C@@H:23]([CH2:39][O:40]C(=O)C)[O:22]1)C1C=CC=CC=1>C(OCC)(=O)C.[Pd]>[OH:20][CH:21]1[O:22][C@H:23]([CH2:39][OH:40])[C@H:24]([OH:35])[C@H:25]([OH:31])[C@H:26]1[NH:27][C:28]([CH3:29])=[O:30]

Komponenten

4

Edukt 1

HCID 58409195(2-{2-[2-((2R,3R,4R,5R,6R)-4,5-Diacetoxy-6-acetoxymethyl-3-acetylamino-tetrahydro-pyran-2-yloxy)-ethoxy]-ethoxy}-ethoxy)-acetic acid benzyl ester

Produkt 1

HCID 35717N-Acetyl-D-GalactosamineAusbeute 109,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

The above prepared (2-{2-[2-((2R,3R,4R,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-3-acetylamino-tetrahydro-pyran-2-yloxy)-ethoxy]-ethoxy}-ethoxy)-acetic acid benzyl ester (15.7 g, 25 mmol) was dissolved in 525 mL of ethyl acetate and hydrogenated over 1.6 g of Pd/C: (10%) under 1 atm. Of H2 at ambient temperature for 3 h. Filtration over Celite, evaporation of the solvent, followed by flash chromatography (SiO2, CH2Cl2/MeOH 80/20) gave 6.07 g of the title compound as a brownish gum MS (ISP): 536.5 [M−H]−.

Aufarbeitung

  1. filtrationFiltration
  2. customover Celite, evaporation of the solvent

Quellen und Nachweise

ORD-Eintrag
ord-0a02fa6e8a264ce9aa1d67b35a4188e2
Quelldatensatz
uspto-grants-2016_02
Patentnummer
US09249179B2

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