Silane, bromotriethyl- → alpha-Acetobromogalactose

HRID 1772999

Reaktionsgleichung

Reaktionsgleichung von HRID 1772999
C(O[C@@H:5]1[O:22][C@H:21]([CH2:23][O:24][C:25](=[O:27])[CH3:26])[C@H:16]([O:17][C:18](=[O:20])[CH3:19])[C@H:11]([O:12][C:13](=[O:15])[CH3:14])[C@H:6]1[O:7][C:8](=[O:10])[CH3:9])(=O)C.[Br:28][Si](CC)(CC)CC.C(=O)([O-])O.[Na+]>ClCCl.[Bi](Br)(Br)Br>[C:8]([O:7][C@@H:6]1[C@@H:11]([O:12][C:13](=[O:15])[CH3:14])[C@@H:16]([O:17][C:18](=[O:20])[CH3:19])[C@@H:21]([CH2:23][O:24][C:25](=[O:27])[CH3:26])[O:22][C@@H:5]1[Br:28])(=[O:10])[CH3:9]

Komponenten

6

Edukt 3

HCID 70680Silane, bromotriethyl-HCID 94752beta-D-Galactose pentaacetateHCID 516892Sodium Bicarbonate

Produkt 1

HCID 2734143alpha-AcetobromogalactoseAusbeute 100,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 82232bismuth(III) bromideKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

β-D-Galactose pentaacetate (5.00 g, 12.8 mmol) and bismuth(III) bromide (287 mg, 640 μmol) were dissolved in dichloromethane (25 mL), the solution was added with bromotriethylsilane (6.76 mL, 51.2 mmol), and the mixture was stirred at room temperature for 3 hours under an argon atmosphere. The reaction mixture was poured into aqueous saturated sodium hydrogencarbonate cooled on ice, then the mixture was extracted with dichloromethane, and the organic layer was washed with brine. The organic layer was dried over sodium sulfate, and the solvent was removed to obtain 2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl bromide (5.30 g, quantitative).

Aufarbeitung

  1. temperaturecooled on ice
  2. extractionthe mixture was extracted with dichloromethane
  3. washthe organic layer was washed with brine
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. customthe solvent was removed

Quellen und Nachweise

ORD-Eintrag
ord-dc0815c0857f49c2ac0db63c74bd1076
Quelldatensatz
uspto-grants-2016_02
Patentnummer
US09250232B2

Verknüpfte Notizen

Wird geladen…