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Acetone → 4-(Hydroxymethyl)phenyl-alpha-D-galactopyranoside tetraacetate

HRID 863780
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 863780
[C:1]([O:4][C@@H:5]1[C@@H:19]([O:20][C:21](=[O:23])[CH3:22])[C@@H:18]([O:24][C:25](=[O:27])[CH3:26])[C@@H:17]([CH2:28][O:29][C:30](=[O:32])[CH3:31])[O:16][C@@H:6]1[O:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14]Br)=[CH:10][CH:9]=1)(=[O:3])[CH3:2].CC(C)=[O:35]>[N+]([O-])([O-])=O.[Ag+]>[C:1]([O:4][C@@H:5]1[C@@H:19]([O:20][C:21](=[O:23])[CH3:22])[C@@H:18]([O:24][C:25](=[O:27])[CH3:26])[C@@H:17]([CH2:28][O:29][C:30](=[O:32])[CH3:31])[O:16][C@@H:6]1[O:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][OH:35])=[CH:10][CH:9]=1)(=[O:3])[CH3:2]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

4

Edukt 2

HCID 180AcetoneHCID 539280404-Bromomethylphenyl 2,3,4,6-tetra-O-acetyl-alpha-D-galactopyranoside

Produkt 1

HCID 538764924-(Hydroxymethyl)phenyl-alpha-D-galactopyranoside tetraacetateAusbeute 56 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 24470Silver NitrateKatalysator

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

A solution of 1.89 g of the compound 2 in 80 ml of acetone is mixed with an equal volume of a 0.1N aqueous solution of silver nitrate. The mixture is stirred at 25° C. for 2 h, the acetone is then evaporated off under reduced pressure, the remaining aqueous phase is extracted with CH2Cl2 and the extract is washed with water and then dried over anhydrous sodium sulfate, filtered and evaporated to dryness under reduced pressure. The dry residue obtained (1.52 g) is then purified by flash chromatography on a column of silica (solvent: hexane/ethyl acetate: 60/40 v/v). The product 4 (0.94 g) is obtained with a yield of 56%.

Aufarbeitung

  1. customthe acetone is then evaporated off under reduced pressure
  2. extractionthe remaining aqueous phase is extracted with CH2Cl2
  3. washthe extract is washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. customevaporated to dryness under reduced pressure
  7. customThe dry residue obtained (1.52 g)
  8. customis then purified by flash chromatography on a column of silica (solvent: hexane/ethyl acetate: 60/40 v/v)

Quellen und Nachweise

ORD-Eintrag
ord-bab7c0ef892342cfbe9676069e15dad2
Quelldatensatz
uspto-grants-1996_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05561119

Notizen zur Reaktion

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