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| | 2,3,4,6-TETRA-O-BENZYL-ALPHA-D-GLUCOPYRANOSE Basic information |
| Product Name: | 2,3,4,6-TETRA-O-BENZYL-ALPHA-D-GLUCOPYRANOSE | | Synonyms: | 2,3,4,6-Tetra-O-benzyl-alpha-D-glucose (for Voglibose);2,3,4,6-TETRA-O-BENZYL-D-GLUCOPYRANOSIDE;2,3,4,6-TETRA-O-BENZOYL-D-GLUCOPYRANOSE;2,3,4,6-Tetra-O-benzyl-alpha-D-glucose;benzylglucopyranose;6-Tetra-O-benzyl-D-glucopyranose;2,3,4,6-tetra-o-benzyl-d-glucose;2,3,4,6-Tetra-o-benzyl-D-glucopyransoe | | CAS: | 6564-72-3 | | MF: | C34H36O6 | | MW: | 540.66 | | EINECS: | 667-304-9 | | Product Categories: | Pharmaceutical Intermediates;6564-72-3 | | Mol File: | 6564-72-3.mol |  |
| | 2,3,4,6-TETRA-O-BENZYL-ALPHA-D-GLUCOPYRANOSE Chemical Properties |
| Melting point | 151-156 °C | | Boiling point | 672.4±55.0 °C(Predicted) | | density | 1.22 | | storage temp. | Sealed in dry,Store in freezer, under -20°C | | pka | 11.87±0.70(Predicted) | | Water Solubility | Soluble in CHCl3. Insoluble in water. | | LogP | 5.9 at 20℃ and pH6.5 | | CAS DataBase Reference | 6564-72-3(CAS DataBase Reference) |
| | 2,3,4,6-TETRA-O-BENZYL-ALPHA-D-GLUCOPYRANOSE Usage And Synthesis |
| Description | 2,3,4,6-Tetra-O-benzyl-D-glucopyranose is a selectively protected intermediate, where the anomeric 1-O-hydroxyl group is free. This hemiacetal has been used successfully as an intermediate for glucosylation couplings, where it was converted into 2,3,4,6-tetra-O-benzyl-D-glucopyranose trichloroacetimidate using trichloroacetonitrile in the presence of a base such as potassium carbonate and DBU.
Importantly, this imidate donor with no neighbouring participating groups is commonly used for the selective formation of glucosides. 2,3,4,6-tetra-O-benzyl-D-glucopyranose can also be oxidized to the lactone, or reduced to give the open chain form.
Additionally, 2,3,4,6-tetra-O-benzyl-D-glucopyranose can be used for the preparation of glucono-1,5-lactone hydrazine, which was used, in-turn, to form a glucosylidene-spirocyclopropane. | | Uses | It is the intermediate of Voglibose/Dapagliflozin. An important D-glucopyranose derivative for glucosylations and other reactions 1,2; Preparation of the α-glucopyranosyl chloride, synthesis of 1-C-α-D-glucopyranose derivatives. | | Synthesis | Octa-O-Dissolves benzyl sucrose or octa-O-allyl sucrose in an organic solvent with the addition of hydrochloric acid without prior chromatographic purification, allows it to react for 20-60 minutes at temperatures of 50-60 °C. and then cleans the end product formed by crystallization. (ethanol, isopropanol, acetone, benzene, toluene or mixtures thereof can be used as solvents). |
| | 2,3,4,6-TETRA-O-BENZYL-ALPHA-D-GLUCOPYRANOSE Preparation Products And Raw materials |
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