Hydrogen Bromide → HCID 86654835, compound

HRID 1422551Notes

Reaction equation

HRID 1422551 reaction equation
[CH2:1]([O:8][C@@H:9]1[C@@H:14]([CH2:15][O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[O:13][CH:12]=[CH:11][C@H:10]1[OH:24])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.Br.C(=O)([O-])[O-:28].[Na+].[Na+]>C1COCC1>[CH2:1]([O:8][C@H:9]([C@@H:14]([CH2:15][O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[OH:13])[C@H:10]([OH:24])[CH2:11][CH:12]=[O:28])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 260Hydrogen BromideHCID 962Water2×HCID 10340Sodium CarbonateHCID 10829982HCID 10829982, compound

Product 1

HCID 86654835HCID 86654835, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4,6-di-O-benzyl-D-glucal (4.9 mmol) was dissolved in THF (60 mL). 48% Water solution of hydrobromic acid (0.4 mL) was added and the reaction mixture was stirred at room temperature. After reaction was completed, water (250 mL) was added, and pH of obtained solution was adjusted to 8 using saturated sodium carbonate. Water solution was then extracted with ethyl acetate (3×100 mL). Combined water extracts were washed with water until neutral, and dried over anhydrous sodium sulfate. Solids and solvents were removed and crude product was purified by column chromatography (SilicaGel 60) using hexanes:ethyl acetate as eluents. Pure 4,6-di-O-benzyl-2-deoxy-D-glucose (3.1 mmol, yield 63%) was obtained.

Workup

  1. customAfter reaction
  2. extractionWater solution was then extracted with ethyl acetate (3×100 mL)
  3. washCombined water extracts were washed with water until neutral, and
  4. dry with materialdried over anhydrous sodium sulfate
  5. customSolids and solvents were removed
  6. customcrude product was purified by column chromatography (SilicaGel 60)

Sources & evidence

ORD record
ord-91e77c1254d24b148e0817d4746229fb
Source dataset
uspto-grants-2015_01
Patent number
US08927506B2

Reaction notes

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