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Toluene → 1,6-anhydro-3,4-dideoxy-2-O-phenylcarbamoyl-beta-D-threo-hex-3-enopyranose

HRID 1769246
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1769246
[C:1]1([N:7]=[C:8]=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1(C)C=CC=CC=1.[C@@H:17]12[O:25][CH2:24][C@@H:22]([O:23]1)[CH:21]=[CH:20][C@@H:18]2[OH:19]>C(N(CC)CC)C>[C:1]1([NH:7][C:8]([O:19][C@H:18]2[CH:20]=[CH:21][C@H:22]3[CH2:24][O:25][C@@H:17]2[O:23]3)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1
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Komponenten

5

Edukt 3

HCID 1140TolueneHCID 7672Phenyl isocyanateHCID 118047741,6-anhydro-3,4-dideoxy-beta-D-threo-hex-3-enopyranose

Produkt 1

HCID 867483871,6-anhydro-3,4-dideoxy-2-O-phenylcarbamoyl-beta-D-threo-hex-3-enopyranoseAusbeute 86,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

0.56 g of phenyl isocyanate was added at room temperature to 30 ml of a dry toluene solution containing 0.3 g of 1,6-anhydro-3,4-dideoxy-β-D-threo-hex-3-enopyranose under an inert atmosphere of nitrogen gas. Further, 0.1 ml of triethylamine was added thereto, and the reaction mixture was refluxed under heating for two hours. Completion of the reaction was confirmed by thin layer chromatography, and then the solvent was immediately distilled off under reduced pressure to obtain a syrup crude product. This crude product was purified by silica gel chromatography (ethyl acetate: hexane=1:3) to obtain 0.5 g of the desired product (Compound No. 23). The NMR analytical data of this product are as follows.

Aufarbeitung

  1. temperaturethe reaction mixture was refluxed
  2. temperatureunder heating for two hours
  3. distillationthe solvent was immediately distilled off under reduced pressure
  4. customto obtain a syrup crude product
  5. customThis crude product was purified by silica gel chromatography (ethyl acetate: hexane=1:3)

Quellen und Nachweise

ORD-Eintrag
ord-08c9d44c2ffa44f0bea92146583bbce3
Quelldatensatz
uspto-grants-1995_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05380834

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