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

HRID 1928678Notes

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>CO.C1COCC1>[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]

Participants

Conditions

Temperature: 24 °C

Procedure

((2S,4R)-4-(tert-Butyldimethylsilyloxy)-6-oxo-tetrahydro-2H-pyran-2-yl)methyl acetate (8.36 g, 27.64 mmol) and [tBu2SnOH(Cl)]2 (1.577 g, 2.764 mmol) are dissolved in MeOH/THF mixture (280 mL). The reaction mixture is stirred at 23-25° C. for 27 h. After the solvent is removed under reduced pressure, the remained residue is purified by silica gel chromatography (elution with tBuMeO/hexane mixture) to afford a crude product as white solid (5.59 g, 78%). Recrystallization from n-hexane affords (3.90 g, 54%) of (4R,6S)-4-(tert-butyldimethylsilyloxy)-6-(hydroxymethyl)-tetrahydro-pyran-2-one as white needles. M.p.=102° C. (DSC peak).

Workup

customAfter the solvent is removed under reduced pressure
customthe remained residue is purified by silica gel chromatography (elution with tBuMeO/hexane mixture)
customto afford a crude product as white solid (5.59 g, 78%)
customRecrystallization from n-hexane

Sources & evidence

ORD record: ord-763c997c7ca84c668d4bf6a003e4a926
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08183397B2

Reaction notes

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