Reaction #1447085

ord-4aca3e1e5bf648b3b5485d7056a8314a

Reaction equation

OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@H](O)C(O)O[C@@H]2CO)[C@@H](O)[C@@H](O)[C@@H]1O
mannobiose
CC(=O)N[C@H]1C(O)O[C@H](CO)[C@@H](O)[C@@H]1O
GlcNAc
→
CC(=O)N[C@H]1C(O)O[C@H](CO)[C@@H](O)[C@@H]1O.OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@H](O)C(O)O[C@@H]2CO)[C@@H](O)[C@@H](O)[C@@H]1O
GlcNAc mannobiose

Reactants

OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@H](O)C(O)O[C@@H]2CO)[C@@H](O)[C@@H](O)[C@@H]1O
mannobiose
CC(=O)N[C@H]1C(O)O[C@H](CO)[C@@H](O)[C@@H]1O
GlcNAc
—
4A

Reagents

O=S(=O)([O-])C(F)(F)F.[Ag+]
AgOTf

Solvents

ClCCl
CH2Cl2
ClCCl
CH2Cl2

Conditions

Temperature
-40°CELSIUS
Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    OtherInsoluble materials were removed by passage through silica gel
  2. 2
    workup.ADDITIONthe filtrate was then diluted with EtOAc
  3. 3
    Washwashed with brine, aq. NaHCO3 and brine successively
  4. 4
    Dryingdried over Na2SO4
  5. 5
    Otherevaporated in vacuo
  6. 6
    OtherThe residue was purified by silica gel column chromatography (toluene:EtOAc, 15:1-10:1)

Procedure

To a stirred mixture of Cp2HfCl2 (269.5 mg, 0.710 mmol), AgOTf (365.5 mg, 1.423 mmol), and molecular sieves 4A (3 g) in dry CH2Cl2 (5 mL) was added a solution of mannobiose acceptor (541.1 mg, 0.593 mmol) and GlcNAc-donor (354.0 g, 0.609 mmol) in dry CH2Cl2 (10 mL) at −78° C. The mixture was stirred for 2 h and at −40° C. for 1 h. Insoluble materials were removed by passage through silica gel and the filtrate was then diluted with EtOAc, washed with brine, aq. NaHCO3 and brine successively, dried over Na2SO4, and evaporated in vacuo. The residue was purified by silica gel column chromatography (toluene:EtOAc, 15:1-10:1) to afford compound GlcNAc-mannobiose donor (393.4 mg, 45%).

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07879766B2uspto-grants-2011_02