Trityl chloride → 2,5-anhydro-1,6-di-O-trityl-D-mannitol

HRID 459421

Reaktionsgleichung

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

Komponenten

Reaktionsbedingungen

Temperatur: 100 °C

Versuchsvorschrift

a mixture of 2.35 g (14.33 mmol) of 2,5-anhydro-D-mannitol and 8.79 g (31.53 mmol) of triphenylmethyl chloride in 38 ml of pyridine was stirred at 100° C. for 12 hours. After cooling, the mixture was diluted with CH2Cl2, and washed with aq.HCl (0.78 mol/l), the organic phase was dried over Na2SO4 and the solvent was subsequently removed under reduced pressure. The crude product was purified by means of column chromatography (hexane/ethyl acetate 2:1). Yield: 5.57 g (60% of theory).

Aufarbeitung

temperatureAfter cooling
washwashed with aq
dry with materialHCl (0.78 mol/l), the organic phase was dried over Na2SO4
customthe solvent was subsequently removed under reduced pressure
customThe crude product was purified by means of column chromatography (hexane/ethyl acetate 2:1)

Quellen und Nachweise

ORD-Eintrag: ord-7fb4bc1e69fc4aa29364d80a0361ba01
Quelldatensatz: uspto-grants-2007_03
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07193092B2

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