Water → HCID 10829982, compound

HRID 1422550Notes

Reaction equation

HRID 1422550 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[O:24][Si](C(C)(C)C)(C)C)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O>C1COCC1>[CH2:1]([O:8][C@@H:9]1[C@@H:14]([CH2:15][O:16][CH2:17][C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=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

Participants

4

Reactant 2

HCID 962WaterHCID 67083590HCID 67083590, compound

Product 1

HCID 10829982HCID 10829982, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4,6-Di-O-benzyl-3-O-tert-butyldimethylsilyl-D-glucal (3 mmol) was dissolved in THF (35 mL). Tetrabutyl fluoride (1M solution in THF) (3.5 mL) was added and the reaction mixture was stirred at room temperature overnight, then water (50 mL) was added and the mixture was extracted with ethyl acetate (3×50 mL). Combined organic 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-D-glucal (2.61 mmol, yield 87%) was obtained. mp 53° C.

Workup

  1. extractionthe mixture was extracted with ethyl acetate (3×50 mL)
  2. washCombined organic extracts were washed with water until neutral, and
  3. dry with materialdried over anhydrous sodium sulfate
  4. customSolids and solvents were removed
  5. customcrude product was purified by column chromatography (SilicaGel 60)

Sources & evidence

ORD record
ord-917f4f1e5cc74f0188e153115b2ac07b
Source dataset
uspto-grants-2015_01
Patent number
US08927506B2

Reaction notes

Loading…