Water → 4-O-benzyl-3,6-di-O-acetyl-D-glucose

HRID 1422553Notes

Reaction equation

HRID 1422553 reaction equation
[OH2:1].Br.[CH2:3]([O:10][C@@H:11]1[C@@H:16]([CH2:17][O:18][C:19](=[O:21])[CH3:20])[O:15][CH:14]=[CH:13][C@H:12]1[O:22][C:23](=[O:25])[CH3:24])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[OH2:26].C(=O)(O)[O-].[Na+]>O1CCCC1>[CH2:3]([O:10][C@H:11]([C@@H:16]([CH2:17][O:18][C:19](=[O:21])[CH3:20])[OH:15])[C@H:12]([O:22][C:23](=[O:25])[CH3:24])[C@@H:13]([OH:26])[CH:14]=[O:1])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 516892Sodium BicarbonateHCID 2734732[(2R,3S,4R)-4-acetyloxy-3-phenylmethoxy-3,4-dihydro-2H-pyran-2-yl]methyl acetateHCID 22326455Hydrobromide monohydrate

Product 1

HCID 866548394-O-benzyl-3,6-di-O-acetyl-D-glucose

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

48% Hydrobromic acid water solution (0.5 mL) was added to a mixture of 4-O-benzyl-3,6-di-O-acetyl-D-glucal (5 mmol) in tetrahydrofuran (50 mL), and obtained solution was stirred in room temperature. After reaction was completed (TLC) the reaction mixture was poured into the 10% water solution of sodium bicarbonate (125 mL), and water solution was extracted with ethyl acetate (3×30 mL). Combined organic extracts were washed with water and dried over sodium sulfate. Drying agent and solvents were removed and product was purified by column chromatography (SilicaGel 60 Merck), using hexanes:ethyl acetate as eluents.

Workup

  1. customobtained solution
  2. customAfter reaction
  3. extractionwas extracted with ethyl acetate (3×30 mL)
  4. washCombined organic extracts were washed with water
  5. dry with materialdried over sodium sulfate
  6. customDrying agent and solvents
  7. customwere removed
  8. customproduct was purified by column chromatography (SilicaGel 60 Merck)

Sources & evidence

ORD record
ord-263635c797c5441f9a11b6f5bc0ab991
Source dataset
uspto-grants-2015_01
Patent number
US08927506B2

Reaction notes

Loading…