Hydrochloric Acid → HCID 86638438, Verbindung

HRID 1009862Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1009862
[CH2:1]([O:8][C@@H:9]1[C@@H:15]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C@H:14]([O:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C@@H:13]([CH2:32][O:33][CH2:34][C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[O:12][C:10]1([C:41]1[CH:46]=[C:45]([CH:47]2OCC[O:48]2)[C:44]([CH3:52])=[CH:43][C:42]=1[O:53][CH2:54][C:55]1[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=1)[OH:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl>O1CCCC1>[CH2:1]([O:8][C@@H:9]1[C@@H:15]([O:16][CH2:17][C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[C@H:14]([O:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C@@H:13]([CH2:32][O:33][CH2:34][C:35]2[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=2)[O:12][C:10]1([C:41]1[CH:46]=[C:45]([CH:47]=[O:48])[C:44]([CH3:52])=[CH:43][C:42]=1[O:53][CH2:54][C:55]1[CH:56]=[CH:57][CH:58]=[CH:59][CH:60]=1)[OH:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

4

Edukt 2

HCID 313Hydrochloric AcidHCID 67304124HCID 67304124, Verbindung

Produkt 1

HCID 86638438HCID 86638438, VerbindungAusbeute 102,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a tetrahydrofuran solution (80 mL) of 2,3,4,6-tetra-O-benzyl-1-C-[2-(benzyloxy)-5-(1,3-dioxolan-2-yl)-4-methylphenyl]-D-glucopyranose (10.6 g, 13.0 mmol) cooled in ice was added 6 M hydrochloric acid (80 mL), and the mixture was stirred for 14 hours at room temperature. To the reaction solution was added ice water, and the resulting mixture was extracted with ethyl acetate. The organic layer was washed with a saturated sodium bicarbonate aqueous solution and brine, and dried with anhydrous magnesium sulfate. The drying agent was filtered off, and the solvent was evaporated under reduced pressure. Thus obtained residue was purified with silica gel column chromatography (hexane:ethyl acetate=2:1) to obtain the title compound (10.2 g, quant.) as a yellow oily compound.

Aufarbeitung

  1. extractionthe resulting mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with a saturated sodium bicarbonate aqueous solution and brine
  3. dry with materialdried with anhydrous magnesium sulfate
  4. filtrationThe drying agent was filtered off
  5. customthe solvent was evaporated under reduced pressure
  6. customThus obtained residue was purified with silica gel column chromatography (hexane:ethyl acetate=2:1)

Quellen und Nachweise

ORD-Eintrag
ord-e78f004c8f6c4d3597bc81672de62fe8
Quelldatensatz
uspto-grants-2011_07
Patentnummer
US07973012B2

Notizen zur Reaktion

Wird geladen…