Methanol → (2S,3R,4R,5S,6R)-2-(4-Chloro-3-((2,3-dihydro-1H-inden-5-yl)methyl)phenyl)-6-(hydroxymethyl)-tetrahydro-2H-pyran-3,4,5-triol

HRID 2206799Notes

Reaction equation

HRID 2206799 reaction equation
C([O:8][C@H:9]1[C@H:14]([O:15]CC2C=CC=CC=2)[C@@H:13]([O:23]CC2C=CC=CC=2)[C@H:12]([C:31]2[CH:36]=[CH:35][C:34]([Cl:37])=[C:33]([CH2:38][C:39]3[CH:40]=[C:41]4[C:45](=[CH:46][CH:47]=3)[CH2:44][CH2:43][CH2:42]4)[CH:32]=2)[O:11][C@@H:10]1[CH2:48][O:49]CC1C=CC=CC=1)C1C=CC=CC=1.CO>C1COCC1.[Pd]>[Cl:37][C:34]1[CH:35]=[CH:36][C:31]([C@H:12]2[C@H:13]([OH:23])[C@@H:14]([OH:15])[C@H:9]([OH:8])[C@@H:10]([CH2:48][OH:49])[O:11]2)=[CH:32][C:33]=1[CH2:38][C:39]1[CH:40]=[C:41]2[C:45](=[CH:46][CH:47]=1)[CH2:44][CH2:43][CH2:42]2

Participants

5

Reactant 2

HCID 887MethanolHCID 86714067(2R,3R,4R,5S,6S)-3,4,5-Tris(benzyloxy)-2-(benzyloxymethyl)-6-(4-chloro-3-((2,3-dihydro-1H-inden-5-yl)methyl)phenyl)-tetrahydro-2H-pyran

Product 1

HCID 58340786(2S,3R,4R,5S,6R)-2-(4-Chloro-3-((2,3-dihydro-1H-inden-5-yl)methyl)phenyl)-6-(hydroxymethyl)-tetrahydro-2H-pyran-3,4,5-triolYield 18%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (2R,3R,4R,5S,6S)-3,4,5-tris(benzyloxy)-2-(benzyloxymethyl)-6-(4-chloro-3-((2,3-dihydro-1H-inden-5-yl)methyl)phenyl)- tetrahydro-2H-pyran (122) (425 mg, 0.56 mmol) in THF:MeOH (v/v=1:1)(8 mL) at room temperature was added Pd/C. The mixture was stirred under H2 for 2 h, Pd/C was removed by filtration and the solvent was removed under reduced pressure. The crude product was purified by preparative HPLC to furnish the title compound (42 mg, 0.10 mmol, 18%).

Workup

  1. customPd/C was removed by filtration
  2. customthe solvent was removed under reduced pressure
  3. customThe crude product was purified by preparative HPLC

Sources & evidence

ORD record
ord-7653dddea4964a5c8410ed2bd60fb35b
Source dataset
uspto-grants-2016_06
Patent number
US09371303B2

Reaction notes

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