2,3,4,6-Tetrakis-O-(phenylmethyl)-D-glucopyranose → 1,3,4,5-Tetra-O-benzyl-D-glucitol

HRID 1747017Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1747017
[CH2:1]([O:8][C@@H:9]1[C@@H:14]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C@H:13]([O:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C@@H:12]([CH2:31][O:32][CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[O:11][CH:10]1[OH:40])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[CH2:1]([O:8][C@H:9]([C@@H:14]([O:15][CH2:16][C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)[C@H:13]([O:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C@H:12]([OH:11])[CH2:31][O:32][CH2:33][C:34]1[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=1)[CH2:10][OH:40])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

4

Edukt 2

HCID 109405022,3,4,6-Tetrakis-O-(phenylmethyl)-D-glucopyranoseHCID 21226445Aluminium lithium hydride

Produkt 1

HCID 108752501,3,4,5-Tetra-O-benzyl-D-glucitolAusbeute 95,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a stirred solution of (3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-[(benzyloxy)methyl]oxan-2-ol 1 (25 g, 46.24 mmol) in THF (310 mL) was added solid LiAlH4 (6.14 g, 161.84 mmol) portion-wise at 0° C. and the reaction mixture was stirred at room temperature for 20 h. The reaction mixture was cooled to 0° C. and carefully quenched with with saturated Na2SO4 solution (35 mL) and the reaction mixture was stirred at room temperature for 30 min. Solid was filtered through a celite pad and the filtrate was diluted with ethyl acetate (250 mL). Organic part was separated and washed with saturated aqueous solution of NH4Cl (3×100 mL). The organic phase was dried over Na2SO4, concentrated under reduced pressure to get crude was purified by column chromatography using 100-200 mesh silica gel and eluting with 12% EtOAc/hexane to get (2S,3R,4R,5R)-2,3,4,6-tetrakis(benzyloxy)hexane-1,5-diol 2 (24 g, 95%) as sticky oil.

Aufarbeitung

  1. temperatureThe reaction mixture was cooled to 0° C.
  2. customcarefully quenched with with saturated Na2SO4 solution (35 mL)
  3. stirringthe reaction mixture was stirred at room temperature for 30 min
  4. filtrationSolid was filtered through a celite pad
  5. additionthe filtrate was diluted with ethyl acetate (250 mL)
  6. customOrganic part was separated
  7. washwashed with saturated aqueous solution of NH4Cl (3×100 mL)
  8. dry with materialThe organic phase was dried over Na2SO4
  9. concentrationconcentrated under reduced pressure
  10. customto get crude
  11. customwas purified by column chromatography
  12. washeluting with 12% EtOAc/hexane

Quellen und Nachweise

ORD-Eintrag
ord-a993df325c4d435382c6bbaebf2a14ae
Quelldatensatz
uspto-grants-2015_10
Patentnummer
US09150557B1

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