1,2-Dichloroethane → EtOAc AcCN MeOH

HRID 1488262Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1488262
[O:1]([CH2:12][CH2:13][NH2:14])[C@@H:2]1[O:10][C@@H](C)[C@@H](O)[C@@H](O)[C@@H:3]1O.[CH2:15](Cl)CCl>CN(C=O)C.CN(C1C=CN=CC=1)C>[CH3:13][CH2:12][O:1][C:2]([CH3:3])=[O:10].[C:12]([C:13]#[N:14])([CH3:15])=[O:1].[CH3:2][OH:1]

Komponenten

5

Edukt 2

HCID 111,2-DichloroethaneHCID 10954744(2R,3S,4R,5S,6S)-2-(2-Aminoethoxy)-6-methyltetrahydro-2H-pyran-3,4,5-triol

Produkt 1

HCID 131736857EtOAc AcCN MeOH

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of N-[(benzyl)carbonyl]-L-glutei acid (1.1 g, 3.91 mmol) and 2-amino ethyl α-L-fucopyranoside (2.026 g, 9.78 mmol) in DMF (10 mL) was added EDC (3.00 g, 15.64 mmol) and DMAP (0.048 g, 0.391 mmol). After stirring at rt for 24 hr, the reaction mixture was concentrated and the residue was purified by flash chromatography on silica gel (80 g), eluting with 100% EtOAc for 5 column volume and then isocratic EtOAc:AcCN:MeOH 6:1:1 to give the title compound. 1H NMR (CD3OD) δ 7.38-7.29 (m, 5H), 5.13-5.05 (m, 2H), 4.76 (s, 2H), 4.09 (dd, J=5.3, 8.6, 1H), 3.95-3.91 (m, 2H), 3.74-3.65 (m, 6H), 3.53-3.25 (m, 8H), 2.30 (t, J=7.5, 2H), 2.06-2.04 (m, 1H), 1.92-1.89 (m, 1H), 1.19 (d, J=6.5, 6H).

Aufarbeitung

  1. concentrationthe reaction mixture was concentrated
  2. customthe residue was purified by flash chromatography on silica gel (80 g)
  3. washeluting with 100% EtOAc for 5 column volume

Quellen und Nachweise

ORD-Eintrag
ord-898a35cc7f384b32add5da09d1b826d2
Quelldatensatz
uspto-grants-2016_08
Patentnummer
US09427475B2

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