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

HRID 1294441

Reaktionsgleichung

Reaktionsgleichung von HRID 1294441
[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-75f8de51bba34535985917060252b27d
Quelldatensatz
uspto-grants-2007_07
Patentnummer
US07241595B2

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