Acetic Anhydride → HCID 178476368, Verbindung

HRID 991145

Reaktionsgleichung

Reaktionsgleichung von HRID 991145
[CH3:1][C:2]1([CH3:31])[CH2:7][C:6](=[O:8])[C:5](=[C:9]([NH:11][C@@H:12]2[C@@H:25]([OH:26])[C@H:24]([OH:27])[C@@H:23]([CH2:28][OH:29])[O:22][C@@H:13]2[O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH3:10])[C:4](=[O:30])[CH2:3]1.C(O[C:36](=[O:38])[CH3:37])(=O)C>N1C=CC=CC=1>[CH3:1][C:2]1([CH3:31])[CH2:7][C:6](=[O:8])[C:5](=[C:9]([NH:11][C@@H:12]2[C@@H:25]([O:26][C:6](=[O:8])[CH3:5])[C@H:24]([O:27][C:13](=[O:14])[CH3:12])[C@@H:23]([CH2:28][O:29][C:36](=[O:38])[CH3:37])[O:22][C@@H:13]2[O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH3:10])[C:4](=[O:30])[CH2:3]1

Komponenten

4

Edukt 2

HCID 7918Acetic AnhydrideHCID 1784645382-[1-[[(2S,3R,4R,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-2-phenylmethoxyoxan-3-yl]amino]ethylidene]-5,5-dimethylcyclohexane-1,3-dione

Produkt 1

HCID 178476368HCID 178476368, VerbindungAusbeute 90 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Benzyl 2-Deoxy-2-[1-(4,4-dimethyl-2,6-dioxocyclohex-1-ylidene)ethylamino]-α-D-glucopyranoside (400 mg, 0.92 mmol) was dissolved in pyridine (6 ml) and cooled to 0° C., then acetic anhydride (10 ml) was added dropwise. The solution was stirred at room temperature overnight, then evaporated. The residue was purified by chromatography using EtOAc/hexane 3:1 to give Benzyl 2-Deoxy-2-[1-(4,4-dimethyl-2,6-dioxocyclohex-1-ylidene)-ethylamino]-3,4,6-tri-O-acetyl-α-D-glucopyranoside (11) (465 mg, 90%).

Aufarbeitung

  1. customevaporated
  2. customThe residue was purified by chromatography

Quellen und Nachweise

ORD-Eintrag
ord-15d4acf558fc46d6bdb6730971eaf397
Quelldatensatz
uspto-grants-2002_10
Patentnummer
US06462183B1

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