Reacción #162037

ord-da7c75efe12d4bef997b557cd751a63f

Ecuación de reacción

CCCCCCCCCCCCCCCCCC(=O)NCCCO[C@@H]1O[C@H](COC(=O)c2ccccc2)[C@@H](O[C@H]2O[C@H](COC(=O)c3ccccc3)[C@@H](O[C@H]3O[C@H](COC(=O)c4ccccc4)[C@@H](O[C@H]4O[C@H](COC(=O)c5ccccc5)[C@@H](OC(=O)c5ccccc5)[C@H](OC(=O)c5ccccc5)[C@H]4OC(=O)c4ccccc4)[C@H](OC(=O)c4ccccc4)[C@H]3OC(=O)c3ccccc3)[C@H](OC(=O)c3ccccc3)[C@H]2OC(=O)c2ccccc2)[C@H](OC(=O)c2ccccc2)[C@H]1OC(=O)c1ccccc1
Glycoside
CCCCCCCCCCCCCCCCCC(=O)NCCCO[C@@H]1O[C@H](COC(=O)c2ccccc2)[C@@H](O[C@H]2O[C@H](COC(=O)c3ccccc3)[C@@H](O[C@H]3O[C@H](COC(=O)c4ccccc4)[C@@H](O[C@H]4O[C@H](COC(=O)c5ccccc5)[C@@H](OC(=O)c5ccccc5)[C@H](OC(=O)c5ccccc5)[C@H]4OC(=O)c4ccccc4)[C@H](OC(=O)c4ccccc4)[C@H]3OC(=O)c3ccccc3)[C@H](OC(=O)c3ccccc3)[C@H]2OC(=O)c2ccccc2)[C@H](OC(=O)c2ccccc2)[C@H]1OC(=O)c1ccccc1
3-Stearamidopropyl 2,3,4,6-tetra-O-benzoyl-α-D-glucopyranosyl-(1→4)-2,3,6-tri-O-benzoyl-α-D-glucopyranosyl-(1→4)-2,3,6-tri-O-benzoyl-α-D-glucopyranosyl-(1→4)-2,3,6-tri-O-benzoyl-β-D-glucopyranoside
C[O-].[Na+]
NaOMe
→
CCCCCCCCCCCCCCCCCC(=O)NCCCO[C@@H]1O[C@H](CO)[C@@H](O[C@H]2O[C@H](CO)[C@@H](O[C@H]3O[C@H](CO)[C@@H](O[C@H]4O[C@H](CO)[C@@H](O)[C@H](O)[C@H]4O)[C@H](O)[C@H]3O)[C@H](O)[C@H]2O)[C@H](O)[C@H]1O
white solid
Rendimiento 99.7%
CCCCCCCCCCCCCCCCCC(=O)NCCCO[C@@H]1O[C@H](CO)[C@@H](O[C@H]2O[C@H](CO)[C@@H](O[C@H]3O[C@H](CO)[C@@H](O[C@H]4O[C@H](CO)[C@@H](O)[C@H](O)[C@H]4O)[C@H](O)[C@H]3O)[C@H](O)[C@H]2O)[C@H](O)[C@H]1O
3-Stearamidopropyl α-D-glucopyranosyl-(1→4)-α-D-glucopyranosyl-(1→4)-α-D-glucopyranosyl-(1→4)-β-D-glucopyranoside
Rendimiento 99.7%

Reactantes

CCCCCCCCCCCCCCCCCC(=O)NCCCO[C@@H]1O[C@H](COC(=O)c2ccccc2)[C@@H](O[C@H]2O[C@H](COC(=O)c3ccccc3)[C@@H](O[C@H]3O[C@H](COC(=O)c4ccccc4)[C@@H](O[C@H]4O[C@H](COC(=O)c5ccccc5)[C@@H](OC(=O)c5ccccc5)[C@H](OC(=O)c5ccccc5)[C@H]4OC(=O)c4ccccc4)[C@H](OC(=O)c4ccccc4)[C@H]3OC(=O)c3ccccc3)[C@H](OC(=O)c3ccccc3)[C@H]2OC(=O)c2ccccc2)[C@H](OC(=O)c2ccccc2)[C@H]1OC(=O)c1ccccc1
Glycoside
CCCCCCCCCCCCCCCCCC(=O)NCCCO[C@@H]1O[C@H](COC(=O)c2ccccc2)[C@@H](O[C@H]2O[C@H](COC(=O)c3ccccc3)[C@@H](O[C@H]3O[C@H](COC(=O)c4ccccc4)[C@@H](O[C@H]4O[C@H](COC(=O)c5ccccc5)[C@@H](OC(=O)c5ccccc5)[C@H](OC(=O)c5ccccc5)[C@H]4OC(=O)c4ccccc4)[C@H](OC(=O)c4ccccc4)[C@H]3OC(=O)c3ccccc3)[C@H](OC(=O)c3ccccc3)[C@H]2OC(=O)c2ccccc2)[C@H](OC(=O)c2ccccc2)[C@H]1OC(=O)c1ccccc1
3-Stearamidopropyl 2,3,4,6-tetra-O-benzoyl-α-D-glucopyranosyl-(1→4)-2,3,6-tri-O-benzoyl-α-D-glucopyranosyl-(1→4)-2,3,6-tri-O-benzoyl-α-D-glucopyranosyl-(1→4)-2,3,6-tri-O-benzoyl-β-D-glucopyranoside
—
solution
C[O-].[Na+]
NaOMe

Reactivos

Ninguno

Disolventes

C1CCOC1.CO
MeOH THF

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    Filtraciónthe solution filtered before the solvent
  2. 2
    Otrowas evaporated
  3. 3
    Otroto yield the white solid product which
  4. 4
    Otrowas triturated with EtOAc
  5. 5
    Otrothe solvent decanted (×3)
  6. 6
    OtroThe solid was dried under vacuum

Procedimiento

Glycoside 126 (377 mg, 161 μmol) was dissolved in MeOH/THF 1:1 (10 mL). NaOMe (60 μL of an 11M solution) was added and the solution was stirred at room temperature for 24 hrs. The mixture was neutralized with acidic resin and the solution filtered before the solvent was evaporated to yield the white solid product which was triturated with EtOAc and the solvent decanted (×3). The solid was dried under vacuum to yield 159 mg of the white solid product (quantitative) which was reacted on without further purification or characterisation.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US08828952B2uspto-grants-2014_09