Thiophenol → 1-(Phenylthio)-2-phthalimidyl-1,2-dideoxy-beta-D-glucopyranose triacetate

HRID 613658Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 613658
C(O[C@@H:5]1[O:18][C@H:17]([CH2:19][O:20][C:21](=[O:23])[CH3:22])[C@@H:12]([O:13][C:14](=[O:16])[CH3:15])[C@H:7]([O:8][C:9](=[O:11])[CH3:10])[C@H:6]1[N:24]1[C:28](=[O:29])[C:27]2=[CH:30][CH:31]=[CH:32][CH:33]=[C:26]2[C:25]1=[O:34])(=O)C.B(F)(F)F.CCOCC.[C:44]1([SH:50])[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1.C(OCC)(=O)C>ClCCl>[C:9]([O:8][C@H:7]1[C@H:12]([O:13][C:14](=[O:16])[CH3:15])[C@@H:17]([CH2:19][O:20][C:21](=[O:23])[CH3:22])[O:18][C@@H:5]([S:50][C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)[C@@H:6]1[N:24]1[C:28](=[O:29])[C:27]2=[CH:30][CH:31]=[CH:32][CH:33]=[C:26]2[C:25]1=[O:34])(=[O:11])[CH3:10]

Komponenten

6

Edukt 4

HCID 7969ThiophenolHCID 8000Boron trifluoride etherateHCID 8857Ethyl AcetateHCID 2728904beta-D-Glucopyranose, 2-deoxy-2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-, 1,3,4,6-tetraacetate

Produkt 1

HCID 110496911-(Phenylthio)-2-phthalimidyl-1,2-dideoxy-beta-D-glucopyranose triacetate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

3.82 g (0.008 Mol) of 1,3,4,6-tetra-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranose was dissolved in 80 ml of anhydrous dichloromethane and stirred at 0° C. under an atmosphere of nitrogen. To this solution, 4.0 ml (0.032 Mol) of boron trifluoride diethyl etherate was slowly added. This was followed by 2.2 ml (0.021 Mol) of thiophenol. The resulting solution was stirred at 0° C. for 4 hr. and at RT for 2 hr. and then poured into a mixture of ethyl acetate (500 ml) and ice-cold saturated sodium bicarbonate solution (200 ml).

Aufarbeitung

  1. stirringThe resulting solution was stirred at 0° C. for 4 hr

Quellen und Nachweise

ORD-Eintrag
ord-587becf04bbe4b90a64748b579785dea
Quelldatensatz
uspto-grants-1999_12
Patentnummer
US06008333

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