|
|
| | 4,6-O-Benzylidene-D-glucose Basic information |
| Product Name: | 4,6-O-Benzylidene-D-glucose | | Synonyms: | 4,6-O-Benzylidene-D-glucopyranoside;4,6-O-Benzylidene-D-glucose;4,6-o-(Phenylmethylene)-D-glucose;D-Glucose, 4,6-o-(phenylmethylene)-;4,6-Benzilidine-D-Glucose;4,5-O-Benzylidene-D-glucopyranose;4,6-0- Benzylidene -d- Glucose;(2R,3R)-2,3-dihydroxy-3-[(4R,5R)-5-hydroxy-2-phenyl-1,3-dioxan-4-yl]propanal | | CAS: | 30688-66-5 | | MF: | C13H16O6 | | MW: | 268.26 | | EINECS: | 1533716-785-6 | | Product Categories: | Intermediates & Fine Chemicals;Chiral Reagents | | Mol File: | 30688-66-5.mol |  |
| | 4,6-O-Benzylidene-D-glucose Chemical Properties |
| 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 |
| WGK Germany | 3 | | HS Code | 2940000080 |
| | 4,6-O-Benzylidene-D-glucose Usage And Synthesis |
| 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. | | 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 |
| | 4,6-O-Benzylidene-D-glucose Preparation Products And Raw materials |
|