| Identification | Back Directory | [Name]
4,6-O-BENZYLIDENE-D-GLUCOPYRANOSE | [CAS]
30688-66-5 | [Synonyms]
4,6-Benzilidine-D-Glucose
4,6-O-Benzylidene-D-glucose
4,6-O-Benzylidene-D-glucopyranose
4,6-o-(Phenylmethylene)-D-glucose
4,5-O-Benzylidene-D-glucopyranose
4,6-O-Benzylidene-D-glucopyranoside
D-Glucose, 4,6-o-(phenylmethylene)- | [EINECS(EC#)]
1533716-785-6 | [Molecular Formula]
C13H16O6 | [MDL Number]
MFCD00057743 | [MOL File]
30688-66-5.mol | [Molecular Weight]
268.26 |
| Chemical Properties | Back Directory | [Melting point ]
183-186 °C | [Boiling point ]
521.6±50.0 °C(Predicted) | [density ]
1.379±0.06 g/cm3(Predicted) | [storage temp. ]
under inert gas (nitrogen or Argon) at 2-8°C | [solubility ]
DMF: 25 mg/ml; DMSO: 14 mg/ml; Ethanol: 25 mg/ml; PBS (pH 7.2): 1 mg/ml | [form ]
A crystalline solid | [pka]
12.44±0.20(Predicted) | [color ]
White to off-white |
| Hazard Information | Back Directory | [Description]
4,6-O-Benzylidene-D-glucose is a useful intermediate for the synthesis of carbohydrates. | [Uses]
4,6-O-Benzylidene-D-glucose is a benzaldehyde derivative with anticancer effects[1]. | [Synthesis]
The general procedure for the synthesis of 4,6-O-benzylidene-D-glucose from (3R,4S,5S,6R)-6-(hydroxymethyl)tetrahydro-2H-pyran-2,3,4,5-tetraol (1.00 g, 5.55 mmol) and benzaldehyde dimethylacetal (1.24 mL, 8.33 mmol) was as follows: (3R,4S,5S,6R)-6-(hydroxymethyl)tetrahydro-2H-pyran-2,3,4,5-tetraol was dissolved in N,N-dimethylformamide (11.0 mL). methyl)tetrahydro-2H-pyran-2,3,4,5-tetrol was dissolved in N,N-dimethylformamide (11.0 mL) and heated to 60 °C to dissolve it completely. Subsequently, benzaldehyde dimethyl acetal and p-toluenesulfonic acid monohydrate (10 mg) were added to the solution and the reaction mixture was stirred at 60 °C for 6 hours. During the reaction, a decompression operation was performed for 10 minutes every hour to remove volatile by-products. Upon completion of the reaction, the solvent was removed by evaporation under reduced pressure. The crude product obtained was purified by silica gel column chromatography using methanol/ethyl acetate (1:10, v/v) as eluent to collect the fraction containing 4,6-O-benzylidene-D-glucopyranose, resulting in a white crystalline product (799.5 mg, 2.98 mmol, 53.7% yield). Note: The (3R,4S,5S,6R)-6-(hydroxymethyl)tetrahydro-2H-pyran-2,3,4,5-tetraol used in the experiment was D-(+)-glucose, which was supplied by Kanto Kagaku Co. | [storage]
Store at -20°C | [References]
[1] E O Pettersen, et al. Effect on protein synthesis and cell survival of the benzaldehyde derivatives sodium benzylidene ascorbate (SBA) and the deuterated compound zilascorb(2H). Anticancer Res. 1991 May-Jun;11(3):1077-81. PMID:1888141 |
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