Reaktion #1362712

ord-ba148674400b429699974ad338e6c017

Reaktionsgleichung

O=[N+]([O-])c1ccc(O[C@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)cc1
4-nitrophenyl-α-D-glucopyranoside
C=COC(=O)CCCCCCCCCCCCCCC
vinyl palmitate
→
CCCCCCCCCCCCCCCC(=O)OC[C@H]1O[C@H](Oc2ccc([N+](=O)[O-])cc2)[C@H](O)[C@@H](O)[C@@H]1O
4-nitrophenyl 6-O-palmitoyl-α-D-glucopyranoside
Ausbeute 84.9%

Edukte

O=[N+]([O-])c1ccc(O[C@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)cc1
4-nitrophenyl-α-D-glucopyranoside
C=COC(=O)CCCCCCCCCCCCCCC
vinyl palmitate

Reagenzien

Keine

Lösungsmittel

CC(C)=O
acetone

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    FiltrationAfter the enzyme was filtered off
  2. 2
    Einengenthe solvent was concentrated
  3. 3
    Sonstigeto afford a crude product in a white wax form, which
  4. 4
    Sonstigewas purified by silica gel chromatography (5% methanol-dichloromethane)

Vorschrift

In 40 ml of acetone were suspended 0.3 g (1 mmol) of 4-nitrophenyl-α-D-glucopyranoside (manufactured by Tokyo Kasei Ind., Ltd.) as marketed, 0.85 g (3 mmol) of vinyl palmitate and 30 mg of Lipase B, and the suspension was reacted in a shaking apparatus at 25° C. for 1 day. After the enzyme was filtered off, the solvent was concentrated to afford a crude product in a white wax form, which was purified by silica gel chromatography (5% methanol-dichloromethane) to give 0.458 g of 4-nitrophenyl 6-O-palmitoyl-α-D-glucopyranoside in a white wax form. Yield 81%

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US06162614uspto-grants-2000_12