Reaktion #2336039

ord-00ae9530b35549fa935a3df071a592d1

Reaktionsgleichung

CC(=O)OCC1(COC(C)=O)OC(OC(C)=O)[C@H](OC(C)=O)[C@@H](OC(C)=O)[C@H]1OC(C)=O
5-C-(acetoxymethyl)-1,2,3,4,6-penta-O-acetyl-L-arabino-hexopyranose
CC(=O)OCC1(COC(C)=O)OC(OC(C)=O)[C@H](OC(C)=O)[C@@H](OC(C)=O)[C@H]1OC(C)=O
5-(acetoxymethyl)-1,2,3,4,6-penta-O-acetyl-L-arabino-hexopyranose
→
OCC(O)(CO)[C@@H]1OC(O)[C@H](O)[C@H]1O
( 8 )
Ausbeute 27.3%
OCC(O)(CO)[C@@H]1OC(O)[C@H](O)[C@H]1O
5-C-Hydroxymethyl-L-arabino-hexofuranose
Ausbeute 27.3%

Edukte

CC(=O)OCC1(COC(C)=O)OC(OC(C)=O)[C@H](OC(C)=O)[C@@H](OC(C)=O)[C@H]1OC(C)=O
5-C-(acetoxymethyl)-1,2,3,4,6-penta-O-acetyl-L-arabino-hexopyranose
CC(=O)OCC1(COC(C)=O)OC(OC(C)=O)[C@H](OC(C)=O)[C@@H](OC(C)=O)[C@H]1OC(C)=O
5-(acetoxymethyl)-1,2,3,4,6-penta-O-acetyl-L-arabino-hexopyranose

Reagenzien

Keine

Lösungsmittel

C[O-].[Na+]
sodium methoxide

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Sonstigeevaporated to oily residue
  2. 2
    SonstigePurification on a silica column with chloroform:methanol (4:1)

Vorschrift

A solution of 5-C-(acetoxymethyl)-1,2,3,4,6-penta-O-acetyl-L-arabino-hexopyranose (7) (4.0 g, 8.7 mmol) in 0.05M methanolic sodium methoxide (50.0 ml) is stirred at room temperature for 2 hours. The reaction mixture is deionized with Amberlite IR-120 (H+) and evaporated to oily residue. Purification on a silica column with chloroform:methanol (4:1) followed by chloroform:methanol (3:2) gives 0.5 g (27%) of (8).

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US05041541uspto-grants-1991_08