Tetrabutylammonium Fluoride → tert-Butyl 2,4-dideoxy-3,5-O-(1-methylethylidene)-D-erythro-hexonate

HRID 2371500Notes

Reaction equation

[Si]([O:18][CH2:19][C@H:20]1[O:25][C:24]([CH3:27])([CH3:26])[O:23][C@@H:22]([CH2:28][C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH2:21]1)(C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[OH:18][CH2:19][C@H:20]1[O:25][C:24]([CH3:26])([CH3:27])[O:23][C@@H:22]([CH2:28][C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH2:21]1

Participants

Conditions

Temperature: -15 °C

Procedure

To a solution of 100 ml of anhydrous tetrahydrofuran containing 12.13 g (0.0243 mol) of tert-butyl [(4R,6S)-6-[(tert-butyldiphenylsilyloxy)methyl]-2,2-dimethyl-1,3-dioxane-4-yl]acetate was added 26.75 ml (0.0268 mol) of the 1 M solution of tetrabutylammonium fluoride in tetrahydrofuran with stirring at -15° C. and reacted for 2.5 hours at 0° to 5° C. The reaction solution was subjected to 120 g of silica gel column chromatography and eluted with ethyl acetate, and the eluate was collected and distilled away under reduced pressure. Again the residue was subjected to silica gel column chromatography and eluted [eluent: methylene chloride-acetonitrile (4:1)]. The first fraction was discarded and successive elution gave 5.52 g of tert-butyl [(4R,6S)-6-(hydroxymethyl)-2,2-dimethyl-1,3-dioxane-4-yl]acetate as syrups (yield: 87%).

Workup

customreacted for 2.5 hours at 0° to 5° C
washeluted with ethyl acetate
customthe eluate was collected
distillationdistilled away under reduced pressure
washeluted [eluent: methylene chloride-acetonitrile (4:1)]
washsuccessive elution

Sources & evidence

ORD record: ord-192a5d509e634b8593acf167322c303d
Source dataset: uspto-grants-1992_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05093363

Reaction notes

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