Trimethylsilyl triflate → Ethyl 2,3,4,6-tetra-O-acetyl-1-thio-beta-D-galactopyranoside

HRID 2086377

Reaktionsgleichung

Reaktionsgleichung von HRID 2086377
[C:1]([O:4][C@H:5]([C@H:8]([C@H:13]([C@@H:18]([CH2:23][O:24][C:25](=[O:27])[CH3:26])[O:19][C:20](=[O:22])[CH3:21])[O:14][C:15](=[O:17])[CH3:16])[O:9][C:10](=O)C)C=O)(=[O:3])[CH3:2].[CH2:28]([S:30][Si](C)(C)C)[CH3:29].FC(F)(F)S(O[Si](C)(C)C)(=O)=O>C(Cl)Cl>[C:25]([O:24][C@@H:23]1[C@@H:18]([O:19][C:20](=[O:22])[CH3:21])[C@@H:13]([O:14][C:15](=[O:17])[CH3:16])[C@@H:8]([CH2:5][O:4][C:1](=[O:3])[CH3:2])[O:9][C@H:10]1[S:30][CH2:28][CH3:29])(=[O:27])[CH3:26]

Komponenten

5

Edukt 3

HCID 65367Trimethylsilyl triflateHCID 81232D-galactose, 2,3,4,5,6-pentaacetateHCID 2733426(Ethylthio)trimethylsilane

Produkt 1

HCID 10572588Ethyl 2,3,4,6-tetra-O-acetyl-1-thio-beta-D-galactopyranosideAusbeute 89 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

A mixture of galactose pentaacetate (38.00 g, 97.43 mmol), (ethylthio)trimethylsilane (19.60 g, 146.15 mmol) and trimethylsilyl trifluoromethanesulfonate (23.60 g, 106.20 mmol) in CH2Cl2 (150 ml) was stirred overnight at room temperature. The reaction mixture was diluted with CH2Cl2 (150 ml) and washed with 1M Na2CO3 solution (300 ml), water (300 ml), dried over MgSO4 and concentrated. The residue was crystallised from hexane/diisopropyl ether 1:1 (v/v) to give ethyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-galactopyranoside (34.00 g, 89%).

Aufarbeitung

  1. washwashed with 1M Na2CO3 solution (300 ml), water (300 ml)
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated
  4. customThe residue was crystallised from hexane/diisopropyl ether 1:1 (v/v)

Quellen und Nachweise

ORD-Eintrag
ord-271527c23872455486f25618a7eb7281
Quelldatensatz
uspto-grants-2004_04
Patentnummer
US06723843B2

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