반응 #162037

ord-da7c75efe12d4bef997b557cd751a63f

반응 방정식

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
수율 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
수율 99.7%

반응물

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

시약

없음

용매

C1CCOC1.CO
MeOH THF

반응 조건

상세 조건
See reaction.notes.procedure_details.

후처리

  1. 1
    여과the solution filtered before the solvent
  2. 2
    기타was evaporated
  3. 3
    기타to yield the white solid product which
  4. 4
    기타was triturated with EtOAc
  5. 5
    기타the solvent decanted (×3)
  6. 6
    기타The solid was dried under vacuum

실험 절차

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.

출처

DOI: 10.6084/m9.figshare.5104873.v1특허: US08828952B2uspto-grants-2014_09