Benzyl Bromide → 2,3,4,6-Tetra-O-benzyl-alpha-D-galactopyranosyl Fluoride

HRID 1016226

Reaktionsgleichung

Reaktionsgleichung von HRID 1016226
[C@H:1]1([F:12])[O:9][C@H:8]([CH2:10][OH:11])[C@H:6]([OH:7])[C@H:4]([OH:5])[C@H:2]1[OH:3].[CH2:13](Br)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>CN(C=O)C.[Ag]=O>[CH2:13]([O:3][C@@H:2]1[C@@H:4]([O:5][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C@@H:6]([O:7][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C@@H:8]([CH2:10][O:11][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[O:9][C@@H:1]1[F:12])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Komponenten

5

Edukt 2

HCID 7498Benzyl BromideHCID 10921145alpha-D-galactosyl fluoride

Produkt 1

HCID 99590292,3,4,6-Tetra-O-benzyl-alpha-D-galactopyranosyl Fluoride

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 92152Silver(II) oxideKatalysatorHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
-20 °C

Versuchsvorschrift

α-D-galactopyranosyl fluoride (2.30 g, 12.62 mmol) was dissolved in dry DMF (40 ml) and, at −20° C., benzyl bromide (12.95 g, 75.72 mmol) and silver oxide (10 g) were added. The reaction mixture was stirred at −20° C. for 5 h and then at room temperature for 24 h. The salts were then filtered off and the filtrate was evaporated in vacuo. The residue was purified by column chromatography on silica gel (350 g) with 15:1 petroleum ether/ethyl acetate.

Aufarbeitung

  1. waitat room temperature for 24 h
  2. filtrationThe salts were then filtered off
  3. customthe filtrate was evaporated in vacuo
  4. customThe residue was purified by column chromatography on silica gel (350 g) with 15:1 petroleum ether/ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-cffac80fabff41b9adf82ecb8d529601
Quelldatensatz
uspto-grants-2002_11
Patentnummer
US06475486B1

Verknüpfte Notizen

Wird geladen…