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((2S,4R)-4-(tert-butyldimethylsilyloxy)-6-oxotetrahydro-2H-pyran-2-yl)methyl acetate → (4R,6S)-4-(tert-butyldimethylsilyloxy)-6-(hydroxymethyl)-tetrahydropyran-2-one

HRID 1952285
Notes
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Reaction equation

HRID 1952285 reaction equation
C([O:4][CH2:5][C@@H:6]1[CH2:11][C@@H:10]([O:12][Si:13]([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14])[CH2:9][C:8](=[O:20])[O:7]1)(=O)C>C1COCC1.CO.[Sn]>[Si:13]([O:12][C@@H:10]1[CH2:11][C@@H:6]([CH2:5][OH:4])[O:7][C:8](=[O:20])[CH2:9]1)([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 1

HCID 16113281((2S,4R)-4-(tert-butyldimethylsilyloxy)-6-oxotetrahydro-2H-pyran-2-yl)methyl acetate

Product 1

HCID 10659025(4R,6S)-4-(tert-butyldimethylsilyloxy)-6-(hydroxymethyl)-tetrahydropyran-2-oneYield 30%

Reagents, catalysts & solvents 3

HCID 5352426Tin atomCatalystHCID 887MethanolSolventHCID 8028
Tetrahydrofuran
Solvent

Procedure

((2S,4R)-4-(tert-butyldimethylsilyloxy)-6-oxotetrahydro-2H-pyran-2-yl)methyl acetate (VI) (0.625 g, 80% purity, 1.65 mmol) was dissolved in THF (8 mL) and MeOH (8 mL). Tin catalyst (tBu2SnClOH)2 (94 mg, 0.1 eq) was added and the reaction was stirred overnight. Reaction was concentrated and purified by flash chromatography to give pure (4R,6S)-4-(tert-butyldimethylsilyloxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-2-one (VII) (126 mg, 30%). VII was found to contain less than 0.1% of enantiomer.

Workup

  1. customReaction
  2. concentrationwas concentrated
  3. custompurified by flash chromatography

Sources & evidence

ORD record
ord-32dbba9c7c334c15bf91feffaf6c3c98
Source dataset
uspto-grants-2013_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08404870B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes