Tetrabutylammonium Fluoride Trihydrate → (3R,4S,5S,6R)-2-(4-chloro-3-(4-hydroxybenzyl)phenyl)-6-(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol

HRID 628758Notes

Reaction equation

HRID 628758 reaction equation
[Si]([O:8][C:9]1[CH:35]=[CH:34][C:12]([CH2:13][C:14]2[CH:15]=[C:16]([C:21]3([O:32][CH3:33])[C@H:26]([OH:27])[C@@H:25]([OH:28])[C@H:24]([OH:29])[C@@H:23]([CH2:30][OH:31])[O:22]3)[CH:17]=[CH:18][C:19]=2[Cl:20])=[CH:11][CH:10]=1)(C(C)(C)C)(C)C.O.O.O.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[Cl:20][C:19]1[CH:18]=[CH:17][C:16]([C:21]2([O:32][CH3:33])[C@H:26]([OH:27])[C@@H:25]([OH:28])[C@H:24]([OH:29])[C@@H:23]([CH2:30][OH:31])[O:22]2)=[CH:15][C:14]=1[CH2:13][C:12]1[CH:11]=[CH:10][C:9]([OH:8])=[CH:35][CH:34]=1

Participants

4

Reactant 2

HCID 11726816Tetrabutylammonium Fluoride TrihydrateHCID 123784895(3R,4S,5S,6R)-2-(3-(4-((tert-butyldimethylsilyl)oxy)benzyl)-4-chlorophenyl)-6-(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol

Product 1

HCID 11955530(3R,4S,5S,6R)-2-(4-chloro-3-(4-hydroxybenzyl)phenyl)-6-(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triolYield 92.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The crude (3R,4S,5S,6R)-2-(3-(4-((tert-butyldimethylsilyl)oxy)benzyl)-4-chlorophenyl)-6-(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol (9.0 g) was dissolved in tetrahydrofuran (70 mL). To the resulting solution was added tetrabutyl ammonium fluoride trihydrate (22.1 g, 70 mmol). The resulting mixture was stirred at room temperature for 2 hr, and concentrated under a reduced pressure. To the mixture were added ethyl acetate (400 mL) and water (200 mL). The resulting mixture was separated into an aqueous phase and an organic phase. The organic phase was successively washed with water (200 mL×3) and a saturated sodium chloride solution, dried over anhydrous sodium sulphate, and concentrated under a reduced pressure to produce 6.5 g of a crude product, which was directly used in the next reaction without purification.

Workup

  1. concentrationconcentrated under a reduced pressure
  2. additionTo the mixture were added ethyl acetate (400 mL) and water (200 mL)
  3. customThe resulting mixture was separated into an aqueous phase
  4. washThe organic phase was successively washed with water (200 mL×3)
  5. dry with materiala saturated sodium chloride solution, dried over anhydrous sodium sulphate
  6. concentrationconcentrated under a reduced pressure

Sources & evidence

ORD record
ord-98afc736bc7d4739b1a0a3a86ec364bd
Source dataset
uspto-grants-2016_04
Patent number
US09315438B2

Reaction notes

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