Reaction #162031

ord-628078b4457d44d2b5c4780004a6c8d0

Reaction equation

CC(=O)OC[C@H]1O[C@@H](O[C@H]2[C@H](OC(C)=O)[C@@H](OC(C)=O)[C@H](On3cc(CO[C@H]4CC[C@@]5(C)C(CC[C@H]6[C@@H]7CC[C@H]([C@H](C)CCCC(C)C)[C@@]7(C)CC[C@@H]65)C4)nn3)O[C@@H]2COC(C)=O)[C@H](OC(C)=O)[C@@H](OC(C)=O)[C@H]1OC(C)=O
N-glycoside
CC(=O)OC[C@H]1O[C@@H](O[C@H]2[C@H](OC(C)=O)[C@@H](OC(C)=O)[C@H](On3cc(CO[C@H]4CC[C@@]5(C)C(CC[C@H]6[C@@H]7CC[C@H]([C@H](C)CCCC(C)C)[C@@]7(C)CC[C@@H]65)C4)nn3)O[C@@H]2COC(C)=O)[C@H](OC(C)=O)[C@@H](OC(C)=O)[C@H]1OC(C)=O
4-(Cholestan-3β-yl-oxymethyl)[1,2,3]triazol-1-yl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1→4)-2,3,6-tri-O-acetyl-β-D-glucopyranoside
CO.C[O-].[Na+]
NaOMe CH3OH
CO.C[O-].[Na+]
NaOMe CH3OH
→
CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CCC4C[C@@H](OCc5cn(O[C@@H]6O[C@H](CO)[C@@H](O[C@@H]7O[C@H](CO)[C@H](O)[C@H](O)[C@H]7O)[C@H](O)[C@H]6O)nn5)CC[C@]4(C)[C@H]3CC[C@]12C
crude product
CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CCC4C[C@@H](OCc5cn(O[C@@H]6O[C@H](CO)[C@@H](O[C@@H]7O[C@H](CO)[C@H](O)[C@H](O)[C@H]7O)[C@H](O)[C@H]6O)nn5)CC[C@]4(C)[C@H]3CC[C@]12C
4-(Cholestan-3β-yl-oxymethyl)[1,2,3]triazol-1-yl β-D-galactopyranosyl-(1→4)-β-D-glucopyranoside

Reactants

CC(=O)OC[C@H]1O[C@@H](O[C@H]2[C@H](OC(C)=O)[C@@H](OC(C)=O)[C@H](On3cc(CO[C@H]4CC[C@@]5(C)C(CC[C@H]6[C@@H]7CC[C@H]([C@H](C)CCCC(C)C)[C@@]7(C)CC[C@@H]65)C4)nn3)O[C@@H]2COC(C)=O)[C@H](OC(C)=O)[C@@H](OC(C)=O)[C@H]1OC(C)=O
N-glycoside
CC(=O)OC[C@H]1O[C@@H](O[C@H]2[C@H](OC(C)=O)[C@@H](OC(C)=O)[C@H](On3cc(CO[C@H]4CC[C@@]5(C)C(CC[C@H]6[C@@H]7CC[C@H]([C@H](C)CCCC(C)C)[C@@]7(C)CC[C@@H]65)C4)nn3)O[C@@H]2COC(C)=O)[C@H](OC(C)=O)[C@@H](OC(C)=O)[C@H]1OC(C)=O
4-(Cholestan-3β-yl-oxymethyl)[1,2,3]triazol-1-yl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1→4)-2,3,6-tri-O-acetyl-β-D-glucopyranoside
CO.C[O-].[Na+]
NaOMe CH3OH
CO.C[O-].[Na+]
NaOMe CH3OH

Reagents

None

Solvents

CO
CH3OH
CO
CH3OH
CO.ClC(Cl)Cl
CHCl3 CH3OH

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    workup.ADDITIONwas added
  2. 2
    workup.ADDITIONUpon completion, the reaction was neutralised to pH 6 by the addition of Dowex H+ ion-exchange resin
  3. 3
    FiltrationThe solution was filtered
  4. 4
    Concentrationconcentrated
  5. 5
    Dryingdried over P2O5

Procedure

Dry N-glycoside 91 (100 mg, 0.092 mmol) was dissolved in anhydrous CH3OH and a solution of NaOMe/CH3OH (11M, 30 μL) was added dropwise to the mixture at 0° C. under argon. The solution was allowed to stir at RT overnight. After monitoring by TLC, additional anhydrous CH3OH (2 mL) and NaOMe/CH3OH (11M, 50 μL) was added and the reaction mixture found to be pH 11. Upon completion, the reaction was neutralised to pH 6 by the addition of Dowex H+ ion-exchange resin, and the resulting suspension dissolved in CHCl3/CH3OH (1:1) at 40° C. The solution was filtered, concentrated and dried over P2O5 to yield the crude product.

Source

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