| Identification | Back Directory | [Name]
9-O-(1,2:5,6-Di-O-isopropylidene-alpha-D-glucofuranosyl)-9-boratabicyclo[3.3.1]nonane potassium salt | [CAS]
101696-41-7 | [Synonyms]
Borate(1-),[1,2:5,6-bis-O-(1-methylethylidene)-a-D-glucofura...
9-O-(1,2:5,6-Di-O-isopropylidene-a-D-glucofuranosyl)-9-boratabicyclo[3.3.1]nonane, Potassium Salt
9-O-(1,2:5,6-Di-O-isopropylidene-alpha-D-glucofuranosyl)-9-boratabicyclo[3.3.1]nonane potassium salt
Borate(1-),[1,2:5,6-bis-O-(1-methylethylidene)-a-D-glucofuranosato-kO3]-1,5-cyclooctanediylhydro-, potassium, (T-4)- (9CI) | [Molecular Formula]
C20H32BKO6 | [MDL Number]
MFCD16621061 | [MOL File]
101696-41-7.mol | [Molecular Weight]
418.38 |
| Hazard Information | Back Directory | [Uses]
9-O-(1,2:5,6-Di-O-isopropylidene-alpha-D-glucofuranosyl)-9-boratabicyclo[3.3.1]nonane potassium salt is a chiral borohydride reagent for enantioselective reduction of ketones.
| [Synthesis]
9-BBN, by reaction with the chiral alcohol 1,2;5,6-di-O-isopropylidene- α-D-glucofuranose (DPGF) (both commercially available), is transformed into the borinic ester 9-O-DIPGF-9-BBN which, by treatment with a modest excess (1.1-1.5 equiv) of potassium hydride, is completely transformed within 2 h into K-glucoride (9-O-(1,2:5,6-Di-O-isopropylidene-alpha-D-glucofuranosyl)-9-boratabicyclo[3.3.1]nonane potassium salt).
| [Precautions]
K-glucoride (9-O-(1,2:5,6-Di-O-isopropylidene-alpha-D-glucofuranosyl)-9-boratabicyclo[3.3.1]nonane potassium salt) is relatively stable toward disproportionation at rt, especially when the THF solution is stored over excess potassium hydride under a positive pressure of nitrogen. It is usually prepared and stored in THF solution.
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