Sodium Methoxide → 4-cyanophenyl 5-thio-beta-D-xylopyranoside

HRID 2372997

Reaktionsgleichung

Reaktionsgleichung von HRID 2372997
C[O-].[Na+].C([O:7][C@@H:8]1[C@@H:22]([O:23]C(=O)C)[C@H:21]([O:27]C(=O)C)[CH2:20][S:19][C@H:9]1[O:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]#[N:18])=[CH:13][CH:12]=1)(=O)C>CO>[O:10]([C:11]1[CH:12]=[CH:13][C:14]([C:17]#[N:18])=[CH:15][CH:16]=1)[C@@H:9]1[S:19][CH2:20][C@@H:21]([OH:27])[C@H:22]([OH:23])[C@H:8]1[OH:7]

Komponenten

4

Edukt 2

HCID 10942334Sodium MethoxideHCID 150678464-cyanophenyl 2,3,4-tri-O-acetyl-5-thio-beta-D-xylopyranoside

Produkt 1

HCID 150678474-cyanophenyl 5-thio-beta-D-xylopyranosideAusbeute 129,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel2×

Versuchsvorschrift

1.5 ml of a solution of sodium methylate in methanol (8% w/v of Na) are added under an inert atmosphere to a suspension of 10 g (25.4.10-3 ) of 4-cyanophenyl 2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranoside in 200 ml of methanol. The reaction mixture is stirred at room temperature for 30 min, neutralized by the addition of Amberlite® IR 120 H+ resin and filtered. After evaporation to dryness, the residue is crystallized from methanol to give 8.8 g (yield: 73%) of the expected product.

Aufarbeitung

  1. additionneutralized by the addition of Amberlite® IR 120 H+ resin
  2. filtrationfiltered
  3. customAfter evaporation to dryness
  4. customthe residue is crystallized from methanol

Quellen und Nachweise

ORD-Eintrag
ord-2690c1d7c1e84292b406dde4c09028dd
Quelldatensatz
uspto-grants-1992_03
Patentnummer
US05101048

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