4-Hydroxybenzaldehyde → HCID 86585860, compound

HRID 843509Notes

Reaction equation

HRID 843509 reaction equation
[C:1]([O:4][C@@H:5]1[O:27][C@H:26]([CH2:28][O:29]C(=O)C2C=CC=CC=2)[C@@H:16]([O:17]C(=O)C2C=CC=CC=2)[C@H:6]1[O:7]C(=O)C1C=CC=CC=1)(=O)[CH3:2].OC1C=[CH:45][C:42]([CH:43]=[O:44])=[CH:41][CH:40]=1.B(F)(F)F>ClCCl>[O:4]([C:1]1[CH:2]=[CH:45][C:42]([CH:43]=[O:44])=[CH:41][CH:40]=1)[C@@H:5]1[O:27][C@H:26]([CH2:28][OH:29])[C@@H:16]([OH:17])[C@H:6]1[OH:7]

Participants

5

Reactant 3

HCID 1264-HydroxybenzaldehydeHCID 6356Boron trifluorideHCID 81455beta-D-Ribofuranose, 1-acetate 2,3,5-tribenzoate

Product 1

HCID 86585860HCID 86585860, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A suspension of 1-O-acetyl-2,3,5-tri-O-benzoylβ-D-ribofuranose (1 g, 2.0 mmol), p-hydroxybenzaldehyde (0.5 g, 4.1 mmol), and boron trifluoride diethyletherate (0.12 ml, 1 mmol) in 20 ml of dry dichloromethane was stirred overnight at room temperature. The solvent was removed in vacuo and the residue extracted with ethyl acetate and brine. The organic layer was dried with sodium sulfate, filtered and the solvents were removed in vacuo. The residue was not purified further, but suspended in methanol and the pH adjusted to 11 with 1.0 N aqueous NaOH. This was stirred and with occasional readjustment of the pH until t.l.c. on silica gel (eluant 1:1 ethyl acetate/hexanes) indicated only material at the solvent front or baseline. Silica gel was added directly to the reaction material and the solvent removed in vacuo. The powder was added to a column of silica gel and purified by flash chromatography with 100% ethyl acetate as eluant. The title compound was obtained as a colourless syrup.

Workup

  1. customThe solvent was removed in vacuo
  2. extractionthe residue extracted with ethyl acetate and brine
  3. dry with materialThe organic layer was dried with sodium sulfate
  4. filtrationfiltered
  5. customthe solvents were removed in vacuo
  6. customThe residue was not purified further
  7. stirringThis was stirred and with occasional readjustment of the pH until t.l.c
  8. additionSilica gel was added directly to the reaction material
  9. customthe solvent removed in vacuo
  10. additionThe powder was added to a column of silica gel
  11. custompurified by flash chromatography with 100% ethyl acetate as eluant

Sources & evidence

ORD record
ord-495b4d48c6e14db0aabbb7a193b52a7c
Source dataset
uspto-grants-2002_04
Patent number
US06379911B2

Reaction notes

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