Diethyl Ether → Methyl 4-O-(2,3,6-tri-O-benzyl-4-deoxy-4-acetyloxymethy-alpha-D-glucopyranosyl)-2,3,6-tri-O-benzyl-alpha-D-glucopyranoside

HRID 1720183

Reaktionsgleichung

Reaktionsgleichung von HRID 1720183
[CH2:1]([O:8][C@@H:9]1[C@@H:16]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C@H:15]([OH:25])[C@@H:14]([CH2:26][O:27][CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[O:13][C@@H:10]1[O:11][CH3:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:35][CH2:36][O:37][CH2:38][CH3:39]>Cl([O-])(=O)(=O)=O.[Ag+]>[CH2:36]([O:37][C@@H:38]1[C@@H:36]([O:37][CH2:38][C:39]2[CH:4]=[CH:3][CH:2]=[CH:7][CH:6]=2)[C@H:35]([CH2:12][O:11][C:10](=[O:13])[CH3:9])[C@@H:15]([CH2:16][O:17][CH2:18][C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[O:25][C@@H:39]1[O:25][C@@H:15]1[C@@H:14]([CH2:26][O:27][CH2:28][C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=2)[O:13][C@H:10]([O:11][CH3:12])[C@H:9]([O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[C@H:16]1[O:17][CH2:18][C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)[C:35]1[CH:31]=[CH:30][CH:29]=[CH:34][CH:33]=1

Komponenten

4

Edukt 2

HCID 3283Diethyl EtherHCID 10983459(2R,3R,4S,5R,6S)-6-methoxy-4,5-bis(phenylmethoxy)-2-(phenylmethoxymethyl)oxan-3-ol

Produkt 1

HCID 54010971Methyl 4-O-(2,3,6-tri-O-benzyl-4-deoxy-4-acetyloxymethy-alpha-D-glucopyranosyl)-2,3,6-tri-O-benzyl-alpha-D-glucopyranoside

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 24562Silver perchlorateKatalysator

Reaktionsbedingungen

Temperatur
-30 °C

Versuchsvorschrift

Ethereal silver perchlorate (0.08 M, 9.58 ml, 7.67 mmol) is added with stirring at -30° C. to a solution of methyl 2,3,6-tri-O-benzyl-α-D-glucopyranoside (2.592 g, 5.59 mmol), 2,3,6-tri-O-benzyl-1,4-dideoxy-4-acetyloxymethyl-D-gluco-pyranosyl chloride (3.661 g, 6.98 mmol) in ether (20 ml). The mixture is stirred 15 min at -30° C. and silver chloride precipitated. The mixture is filtered through a celite pad, the solids are washed with ether, the filtrate is concentrated under reduced pressure. The residue is dissolved in methylene chloride and the organic layer is washed successively with aqueous sodium thiosulfate and water. The organic layer is dried over sodium sulfate, filtered and concentrated under reduced pressure so as to afford a foam. Flash chromatography on silica gel and elution with a graded mixture of hexane and ethyl acetate will afford methyl 4-O-(2,3,6-tri-O-benzyl-4-deoxy-4-acetyloxymethyl-α-D-glucopyranosyl)-2,3,6-tri-O-benzyl-α-D-glucopyranoside as a foam.

Aufarbeitung

  1. customsilver chloride precipitated
  2. filtrationThe mixture is filtered through a celite pad
  3. washthe solids are washed with ether
  4. concentrationthe filtrate is concentrated under reduced pressure
  5. dissolutionThe residue is dissolved in methylene chloride
  6. washthe organic layer is washed successively with aqueous sodium thiosulfate and water
  7. dry with materialThe organic layer is dried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure so as
  10. customto afford a foam
  11. washFlash chromatography on silica gel and elution
  12. additionwith a graded mixture of hexane and ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-46742bde2673474babe503b8a971d1dd
Quelldatensatz
uspto-grants-1996_04
Patentnummer
US05504078

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