tert-Butyldimethylsilyl chloride → HCID 178464539, Verbindung

HRID 991149Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 991149
[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.[Si:32](Cl)([C:35]([CH3:38])([CH3:37])[CH3:36])([CH3:34])[CH3:33]>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]([OH:26])[C@H:24]([OH:27])[C@@H:23]([CH2:28][O:29][Si:32]([C:35]([CH3:38])([CH3:37])[CH3:36])([CH3:34])[CH3:33])[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 28928tert-Butyldimethylsilyl chlorideHCID 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 178464539HCID 178464539, VerbindungAusbeute 61,1 %

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 (100 mg, 0.23 mmol) was dissolved in dry pyridine (2 ml), cooled to 0° C. and t-butyldimethylsilylchloride (39 mg, 0.26 mmol) added. The reaction mixture was stirred at room temperature overnight. The solution was evaporated, the residue was taken up in CHCl3 (10 ml), washed with water (3 ml), dried over MgSO4 and concentrated. The residue was purified by chromatography using CHCl3/MeOH 10:1 as the mobile phase to give Benzyl 2-Deoxy-2-[1-(4,4-dimethyl-2,6-dioxocyclohex-1-ylidene)ethylamino]-6-O-t-butyldimethylsilyl-α-D-glucopyranoside (15) (77 mg, 61%).

Aufarbeitung

  1. customThe solution was evaporated
  2. washwashed with water (3 ml)
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated
  5. customThe residue was purified by chromatography

Quellen und Nachweise

ORD-Eintrag
ord-7fdda7ac45f3418b82967f661c4a444c
Quelldatensatz
uspto-grants-2002_10
Patentnummer
US06462183B1

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