Trichloroacetonitrile → HCID 90330613, Verbindung

HRID 590685

Reaktionsgleichung

Reaktionsgleichung von HRID 590685
ClC(Cl)(Cl)C(OC1[O:41][C@@H:40]([CH3:42])[C@@H:29]([O:30][CH2:31][C:32]2C=CC(OC)=CC=2)[C@@H:18](OCC2C=CC(OC)=CC=2)[C@@H]1OCC1C=CC(OC)=CC=1)=N.[CH3:45][O:46][C:47]1[CH:82]=[CH:81][C:50]([CH2:51][O:52][C@H:53]2[C@H:59]([O:60][CH2:61][C:62]3[CH:67]=[CH:66][C:65]([O:68][CH3:69])=[CH:64][CH:63]=3)[C@H:58]([O:70][CH2:71][C:72]3[CH:77]=[CH:76][C:75]([O:78][CH3:79])=[CH:74][CH:73]=3)[C@H:57]([CH3:80])[O:56][CH:54]2[OH:55])=[CH:49][CH:48]=1.ClC(Cl)(Cl)C#N.[H-].[Na+].CC1C(=O)C(O)=C(C)O1.[Si](OS(C(F)(F)F)(=O)=O)(C)(C)C>C(OCC)C>[CH3:45][O:46][C:47]1[CH:48]=[CH:49][C:50]([CH2:51][O:52][C@H:53]2[C@H:59]([O:60][CH2:61][C:62]3[CH:67]=[CH:66][C:65]([O:68][CH3:69])=[CH:64][CH:63]=3)[C@H:58]([O:70][CH2:71][C:72]3[CH:73]=[CH:74][C:75]([O:78][CH3:79])=[CH:76][CH:77]=3)[C@H:57]([CH3:80])[O:56][C@H:54]2[O:55][C:42]2[C:40](=[O:41])[CH:29]([CH3:18])[O:30][C:31]=2[CH3:32])=[CH:81][CH:82]=1

Komponenten

8

Edukt 6

HCID 11011TrichloroacetonitrileHCID 19309FuraneolHCID 24758Sodium hydrideHCID 65367Trimethylsilyl triflateHCID 11763113HCID 11763113, VerbindungHCID 90330564HCID 90330564, Verbindung

Produkt 1

HCID 90330613HCID 90330613, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel2×

Versuchsvorschrift

The solution of 2,3,4-tri-O-(4-methoxybenzyl)-L-fucopyranose trichloroacetimidate (a/β mixture, prepared from 85 mmol of 2,3,4-tri-O-(4-methoxybenzyl)-L-fucopyranose and trichloroacetonitrile in the presence of NaH in quantitative yield) in diethyl ether (100 ml) was added to a mixture of 2,5-dimethyl-4-hydroxy-3-oxo-(2H)-furan (85 mmol) and TMS-triflate (1.2 ml) in diethyl ether (200 ml) at −14° C. After 3 hours the cooling bath was removed and the stirring continued for 1 hour. The reaction mixture was diluted with ethyl acetate and extracted with sat. NaHCO3-solution (3×150 ml) and brine (150 ml). The organic phase was dried over Na2SO4 and evaporated. The resulting syrup was purified by column chromatography yielding 23.27 g of 2,5-dimethyl-3-oxo-(2H)-furan-4-yl 2,3,4-tri-O-(4-methoxybenzyl)-α-L-fucopyranoside as a thick yellow syrup in a 1:1 mixture of diastereoisomers. Selected NMR chemical shifts in CDCl3: anomeric protons: 5.32 and 5.57 ppm, J1,2=3.4 Hz; anomeric carbons: 113.81 and 113.95 Hz.

Aufarbeitung

  1. customAfter 3 hours the cooling bath was removed
  2. additionThe reaction mixture was diluted with ethyl acetate
  3. extractionextracted with sat. NaHCO3-solution (3×150 ml) and brine (150 ml)
  4. dry with materialThe organic phase was dried over Na2SO4
  5. customevaporated
  6. customThe resulting syrup was purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-ceee4822e4a846c49414600cd0503d47
Quelldatensatz
uspto-grants-2016_01
Patentnummer
US09234225B2

Verknüpfte Notizen

Wird geladen…