Tetrabutylammonium Fluoride → (4R,6S)-6-(dimethoxymethyl)-tetrahydro-2H-pyran-2,4-diol

HRID 1261816Notes

Reaction equation

[Si]([O:8][C@@H:9]1[CH2:14][C@@H:13]([CH:15]([O:18][CH3:19])[O:16][CH3:17])[O:12][CH:11]([OH:20])[CH2:10]1)(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[CH3:17][O:16][CH:15]([O:18][CH3:19])[C@H:13]1[O:12][CH:11]([OH:20])[CH2:10][C@H:9]([OH:8])[CH2:14]1

Participants

Conditions

Temperature: 25 °C

Procedure

To a solution of 0.47 g of (4R,6S)-4-(tert-butyldimethylsilyloxy)-6-(dimethoxymethyl)-tetrahydro-2H-pyran-2-ol (I′) in 14 mL of tetrahydrofurane, tetra-n-butylammonium fluoride in 14 mL of THF is added. After 15 minutes of stirring at 25° C., the THF is distilled off. The residue is flash chromatographed (methanol). After methanol is distilled off, the title compound is obtained as an oil.

Workup

distillationthe THF is distilled off
customchromatographed (methanol)
distillationAfter methanol is distilled off

Sources & evidence

ORD record: ord-80a13d9d9c5447929913a4152c95e3a8
Source dataset: uspto-grants-2013_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08471045B2

Reaction notes

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