Thiophenol → Phenyl 2,3,4,6-tetra-O-acetyl-1-thio-beta-D-galactopyranoside

HRID 1637427

Reaktionsgleichung

Reaktionsgleichung von HRID 1637427
[C:1]([O:4][C@H:5]([C@H:8]([C@H:13]([C@@H:18]([CH2:23][O:24][C:25](=[O:27])[CH3:26])[O:19][C:20](=[O:22])[CH3:21])[O:14][C:15](=[O:17])[CH3:16])[O:9][C:10](=O)C)C=O)(=[O:3])[CH3:2].[C:28]1([SH:34])[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>C(Cl)Cl>[C:28]1([S:34][C@@H:10]2[O:9][C@H:8]([CH2:5][O:4][C:1](=[O:3])[CH3:2])[C@H:13]([O:14][C:15](=[O:17])[CH3:16])[C@H:18]([O:19][C:20](=[O:22])[CH3:21])[C@H:23]2[O:24][C:25](=[O:27])[CH3:26])[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Komponenten

4

Edukt 2

HCID 7969ThiophenolHCID 81232D-galactose, 2,3,4,5,6-pentaacetate

Produkt 1

HCID 10950254Phenyl 2,3,4,6-tetra-O-acetyl-1-thio-beta-D-galactopyranosideAusbeute 96 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of galactose pentaacetate (5.00 g, 12.8 mmol) in 125 mL of CH2Cl2 is added thiophenol (1.49 mL, 14.1 mmol) and boron trifluoride diethyl ether complex (4.73 mL, 38.4 mmol). The reaction mixture is stirred at room temperature for 5 h and then poured into 200 mL of ice water. The organic layer is washed with saturated NaHCO3 (200 ml), dried over Na2SO4, filtered, concentrated and purified by flash chromatography (35% EtOAc/hexane) to give 5.4 g (96%) of 1-deoxy-1-(phenylthio)-2,3,4,6-tetra-O-acetyl-β-D-galactopyranose 39: Rf 0.22 (35% EtOAc/hexane); 1H NMR (CDCl3, 270 MHz) δ 7.35-7.65 (m, 5 H, ArH), 5.50 (br d, J=3.3 Hz, 1 H, H-4), 5.32 (t, J=9.8 Hz, 1 H, H-2), 5.13 (dd, J=9.8, 3.3 Hz, 1 H, H-3), 4.80 (d, J=9.8 Hz, 1 H, H-1), 4.13-4.32 (m, 2 H, H-6, H-6'), 4.02 (br t, J=6.5 Hz, 1 H, H-5), 2.02-2.23 (4s, 12 H, OAc).

Aufarbeitung

  1. washThe organic layer is washed with saturated NaHCO3 (200 ml)
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. custompurified by flash chromatography (35% EtOAc/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-13e06809a7c340b4bd1d74d850fe752d
Quelldatensatz
uspto-grants-2000_03
Patentnummer
US06040433

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