Diethyl Ether → Deoxynojirimycin

HRID 982176

Reaktionsgleichung

Reaktionsgleichung von HRID 982176
C(OC([N:11]1[C@H:33]([CH2:34][OH:35])[C@@H:24]([O:25]CC2C=CC=CC=2)[C@H:22]([OH:23])[C@@H:13]([O:14]CC2C=CC=CC=2)[CH2:12]1)=O)C1C=CC=CC=1.C(OCC)C>C(O)(=O)C.[Pd]>[NH:11]1[C@H:33]([CH2:34][OH:35])[C@@H:24]([OH:25])[C@H:22]([OH:23])[C@@H:13]([OH:14])[CH2:12]1

Komponenten

5

Edukt 2

HCID 3283Diethyl EtherHCID 10917777N-benzyloxycarbonyl-2,4-di-O-benzyl-1,5-dideoxy-1,5-imino-D-glucitol

Produkt 1

HCID 29435DeoxynojirimycinAusbeute 96 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

The diol (17) (580 mg, 1.2 mmol) was stirred in glacial acetic acid (30 ml) in the presence of palladium black (100 mg) under hydrogen for 3 days, by which time no starting material (Rf 0.2) remained by t.l.c. (diethyl ether). Filtration and removal of the solvent then gave a gum which was purified by ion exchange chromatography with Dowex 50(H+) followed by Amberlite CG-400(Cl-) resins to give 1,5-dideoxy-1,5-imino-D-glucitol (3) (188 mg, 95%), which was crystallized as its hydrochloride salt. m.p. 204°-205° C. (lit.* 203°-206° C.). All spectroscopic data were identical to that of authentic material. --C NMR (D2O) free base δ: 79.0, 72.1, 71.1 (3d, C-2, C-3, C-4), 61.9 (t, C-6), 61.0 (d, C-5), 49.2 (t, C-1). Hydrogen chloride salt δ: 77.1, 68.6, 67.8 (3d, C-2, C-3, C-4), 60.8 (d, C-5), 58.5 (t, C-6), 46.7 (t, C-1). [*Fleet et al., Tetrahedron 43, 979 (1987)].

Aufarbeitung

  1. filtrationFiltration and removal of the solvent
  2. customthen gave a gum which
  3. customwas purified by ion exchange chromatography with Dowex 50(H+)

Quellen und Nachweise

ORD-Eintrag
ord-9cb8c65046eb4964b5d820cc779f95fd
Quelldatensatz
uspto-grants-1991_02
Patentnummer
US04994572

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