Trifluoroacetic acid → Methyl 2,3,5-tri-O-benzyl-L-xylofuranose

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Reaktionsgleichung

[CH2:1]([O:8][C@H:9]1[C@H:15]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C@H:14]([CH2:24][O:25][CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[O:13][CH:10]1[O:11]C)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.F[C:34](F)(F)C(O)=O>O.C(OCC)(=O)C>[CH3:34][C:10]1([O:13][C@@H:14]([CH2:24][O:25][CH2:26][C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)[C@@H:15]([O:16][CH2:17][C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[C@@H:9]1[O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[OH:11]

Komponenten

Reaktionsbedingungen

Temperatur: 0 °C

Versuchsvorschrift

Methyl 2,3,5-tri-O-benzyl-L-xylofuranoside (22.7 g, 56.30 mmol) is dissolved at 0° C. in a 9:1 mixture of trifluoroacetic acid and water (200 mL) and stirred at 0° C. overnight. The mixture is put to dryness under reduced pressure. The oily residue is dissolved in ethyl acetate and washed three times with a saturated solution of sodium bicarbonate. The organic layer is dried over sodium sulfate, filtered and put to dryness under reduced pressure to afford an oil. Flash chromatography on silica gel and elution with a 7:3 mixture of cyclohexane and ethyl acetate yield methyl 2,3,5-tri-O-benzyl-L-xylofuranose as an oil (11.7 g, 53%).

Aufarbeitung

washwashed three times with a saturated solution of sodium bicarbonate
dry with materialThe organic layer is dried over sodium sulfate
filtrationfiltered
customto afford an oil
washFlash chromatography on silica gel and elution
additionwith a 7:3 mixture of cyclohexane and ethyl acetate

Quellen und Nachweise

ORD-Eintrag: ord-0eb5f4b01683457591f7aefafea005cd
Quelldatensatz: uspto-grants-1992_03
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US05097023

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