Tetrabutylammonium Fluoride → HCID 67288226, compound

HRID 2042906Notes

Reaction equation

HRID 2042906 reaction equation
[Cl:1][C:2]1[CH:19]=[CH:18][C:17]([CH:20]2[C@H:25]([O:26][CH2:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[C@@H:24]([O:34][CH2:35][C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)[C@H:23]([O:42][CH2:43][C:44]3[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=3)[C@@H:22]([CH2:50][O:51][CH2:52][C:53]3[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=3)[O:21]2)=[CH:16][C:3]=1[CH2:4][O:5][Si](C(C)C)(C(C)C)C(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[Cl:1][C:2]1[CH:19]=[CH:18][C:17]([CH:20]2[C@H:25]([O:26][CH2:27][C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=3)[C@@H:24]([O:34][CH2:35][C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)[C@H:23]([O:42][CH2:43][C:44]3[CH:45]=[CH:46][CH:47]=[CH:48][CH:49]=3)[C@@H:22]([CH2:50][O:51][CH2:52][C:53]3[CH:54]=[CH:55][CH:56]=[CH:57][CH:58]=3)[O:21]2)=[CH:16][C:3]=1[CH2:4][OH:5]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 67287190(2-Chloro-5-((3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)-tetrahydro-2H-pyran-2-yl)benzyloxy)triisopropylsilane

Product 1

HCID 67288226HCID 67288226, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (2-chloro-5-((3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)-tetrahydro-2H-pyran-2-yl)benzyloxy)triisopropylsilane in THF (500 mL) was added tetrabutylammonium fluoride (1.0 M in THF, 594 mL, 594 mmol) and the reaction mixture stirred at ambient temperature for 2 h. After removal of organic volatiles under reduced pressure, the residue was partitioned between EtOAc and saturated ammonium chloride. The organic layer was separated and the aqueous layer was extracted with EtOAc. The combined organic layers were washed with brine, dried over anhydrous MgSO4, filtered and concentrated in vacuo. The crude residue was purified on column chromatography to provide the titled compound (168 g, 98%, ca. 2:1 mixture of anomers (β:α)) as a white solid.

Workup

  1. customAfter removal of organic volatiles under reduced pressure
  2. customthe residue was partitioned between EtOAc and saturated ammonium chloride
  3. customThe organic layer was separated
  4. extractionthe aqueous layer was extracted with EtOAc
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over anhydrous MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe crude residue was purified on column chromatography

Sources & evidence

ORD record
ord-f89d59cf798e4ff1928df6e8177c816d
Source dataset
uspto-grants-2013_11
Patent number
US08586550B2

Reaction notes

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