Reaktion #162027

ord-152897acbd4f4b1cad29ca1cc4a352df

Reaktionsgleichung

CC(=O)OC[C@H]1O[C@H](O[C@H]2[C@H](OC(C)=O)[C@@H](OC(C)=O)[C@@H](O[C@H]3[C@H](OC(C)=O)[C@@H](OC(C)=O)C(OC(C)=O)O[C@@H]3COC(C)=O)O[C@@H]2COC(C)=O)[C@H](OC(C)=O)[C@@H](OC(C)=O)[C@@H]1OC(C)=O
Maltotriose peracetate
Br.CC(=O)O
HBr HOAc
→
CC(=O)OC[C@H]1O[C@H](Br)[C@H](OC(C)=O)[C@@H](OC(C)=O)[C@@H]1O[C@H]1O[C@H](COC(C)=O)[C@@H](O[C@H]2O[C@H](COC(C)=O)[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]2OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O
bromide
CC(=O)OC[C@H]1O[C@H](Br)[C@H](OC(C)=O)[C@@H](OC(C)=O)[C@@H]1O[C@H]1O[C@H](COC(C)=O)[C@@H](O[C@H]2O[C@H](COC(C)=O)[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]2OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O
2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl-(1→4)-2,3,6-tri-O-acetyl-α-D-glucopyranosyl-(1→4)-2,3,6-tri-O-acetyl-α-D-glucopyranosyl bromide

Edukte

CC(=O)OC[C@H]1O[C@H](O[C@H]2[C@H](OC(C)=O)[C@@H](OC(C)=O)[C@@H](O[C@H]3[C@H](OC(C)=O)[C@@H](OC(C)=O)C(OC(C)=O)O[C@@H]3COC(C)=O)O[C@@H]2COC(C)=O)[C@H](OC(C)=O)[C@@H](OC(C)=O)[C@@H]1OC(C)=O
Maltotriose peracetate
Br.CC(=O)O
HBr HOAc

Reagenzien

Keine

Lösungsmittel

ClCCl
DCM
ClCCl
DCM

Reaktionsbedingungen

Temperatur
0°CELSIUS
Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Sonstigeat 0° C
  2. 2
    Waschenwashed with ice-water (×2), NaHCO3 (sat.) (×2) and brine (×1)
  3. 3
    Trocknenbefore being dried (Na2SO4)
  4. 4
    Sonstigethe solvent evaporated

Vorschrift

Maltotriose peracetate (71)36 (200 mg, 207 μmol) was taken up in DCM (1 mL) and 33% HBr/HOAc (0.7 mL) at 0° C. The mixture was stirred at 0° C. for four hours. The solution was diluted with DCM and washed with ice-water (×2), NaHCO3 (sat.) (×2) and brine (×1), before being dried (Na2SO4) and the solvent evaporated to yield the bromide 72 as white solid which was reacted on without further purification or characterisation.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08828952B2uspto-grants-2014_09