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

HRID 1892148Notes

Reaction equation

HRID 1892148 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 the 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 the 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). Mass (m/z): 389.37 (M++1)

Workup

  1. customDimethylformamide was evaporated under the reduced pressure
  2. washwashed with water
  3. dry with materialThe organic layer was dried over anhydrous sodium sulphate
  4. customThe solvent was evaporated under the 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-39ee8ac7e1e54cd39c14545b17bba096
Source dataset
uspto-grants-2013_08
Patent number
US08507670B2

Reaction notes

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