Imidazole → 5-O-[tert-butyl(diphenyl)silyl]-D-arabinofuranose

HRID 83995

Reaction equation

HRID 83995 reaction equation
[O:1]=[CH:2][C@H:3]([C@@H:5]([C@@H:7]([CH2:9][OH:10])[OH:8])[OH:6])[OH:4].N1C=CN=C1.[C:16]([Si:20]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)Cl)([CH3:19])([CH3:18])[CH3:17]>CN(C)C=O>[Si:20]([O:1][CH2:2][C@H:3]1[O:4][CH:9]([OH:10])[C@@H:7]([OH:8])[C@@H:5]1[OH:6])([C:16]([CH3:19])([CH3:18])[CH3:17])([C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 66308D-ArabinoseHCID 94078tert-Butyldiphenylchlorosilane

Product 1

HCID 671826605-O-[tert-butyl(diphenyl)silyl]-D-arabinofuranose

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

D-Arabinose (200 g) and imidazole (199 g) were placed in a three-neck round bottom flask and connected to high vacuum for 30 minutes. The vacuum was released under nitrogen atmosphere and dimethylformamide (1.8 L) was added to the above mixture at room temperature followed by drop-wise addition of t-butyldiphenylchlorosilane (443 mL) for 10 minutes under a nitrogen atmosphere. The resulting mixture was stirred for 16 hours at the same temperature. Dimethylformamide was evaporated under reduced pressure. The residue was taken up in ethyl acetate and washed with water. The organic layer was dried over anhydrous sodium sulphate. The solvent was evaporated under reduced pressure to obtain a crude residue which was purified by column chromatography over silica gel using 80% ethyl acetate in hexane as eluant to afford the title compound (273 g).

Workup

  1. customDimethylformamide was evaporated under reduced pressure
  2. washwashed with water
  3. dry with materialThe organic layer was dried over anhydrous sodium sulphate
  4. customThe solvent was evaporated under reduced pressure
  5. customto obtain a crude residue which
  6. customwas purified by column chromatography over silica gel using 80% ethyl acetate in hexane as eluant

Sources & evidence

ORD record
ord-27b2e77f54ea48fc8e43c324e87fda9e
Source dataset
uspto-grants-2014_09
Patent number
US08846910B2

Linked notes

Loading…