Water → HCID 58786153, compound

HRID 1375976Notes

Reaction equation

HRID 1375976 reaction equation
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[CH2:19]([O:26][C@@H:27]1[C@@H:32]([O:33][CH2:34][C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[C@H:31]([O:41][CH2:42][C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)[C@@H:30]([CH2:49][O:50][CH2:51][C:52]2[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=2)[O:29][C@H:28]1[C:58]1[CH:63]=[CH:62][CH:61]=[C:60]([CH2:64][O:65][Si](C(C)(C)C)(C2C=CC=CC=2)C2C=CC=CC=2)[CH:59]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.[OH-].[Na+].O>C1COCC1>[CH2:19]([O:26][C@@H:27]1[C@@H:32]([O:33][CH2:34][C:35]2[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=2)[C@H:31]([O:41][CH2:42][C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)[C@@H:30]([CH2:49][O:50][CH2:51][C:52]2[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=2)[O:29][C@H:28]1[C:58]1[CH:63]=[CH:62][CH:61]=[C:60]([CH2:64][OH:65])[CH:59]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 2724141Tetrabutylammonium FluorideHCID 58786101HCID 58786101, compound

Product 1

HCID 58786153HCID 58786153, compoundYield 56.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A 1.0 M THF solution of tetrabutylammonium fluoride (3.8 ml) was added to a solution of (1S)-1,5-anhydro-2,3,4,6-tetra-O-benzyl-1-[3-([[t-butyl(diphenyl)silyl]oxy]methyl) phenyl]-D-glucitol (1.7 g) in THF (10.0 ml) at room temperature and the mixture was stirred for two hours. 10% aqueous solution of sodium hydroxide (3.0 ml) was further added to the reaction mixture and the mixture was refluxed with stirring for one hour. Water was added to the reaction mixture and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated. The residue was purified by silica gel column chromatography (n-hexane-ethyl acetate) to obtain (1S)-1,5-anhydro-2,3,4,6-tetra-O-benzyl-1-[3-(hydroxymethyl)phenyl]-D-glucitol (0.7 g).

Workup

  1. temperaturethe mixture was refluxed
  2. stirringwith stirring for one hour
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationAfter filtration
  7. concentrationthe filtrate was concentrated
  8. customThe residue was purified by silica gel column chromatography (n-hexane-ethyl acetate)

Sources & evidence

ORD record
ord-85dd016c59f74ac0ad294d2b94f12460
Source dataset
uspto-grants-2007_01
Patent number
US07169761B2

Reaction notes

Loading…