Introduction：Basic information about 2,3,4,6-TETRA-O-BENZYL-ALPHA-D-GLUCOPYRANOSE CAS 6564-72-3, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
Table of Contents
- 1. 2,3,4,6-TETRA-O-BENZYL-ALPHA-D-GLUCOPYRANOSE Basic information
- 2. 2,3,4,6-TETRA-O-BENZYL-ALPHA-D-GLUCOPYRANOSE Chemical Properties
- 3. Safety Information
- 4. 2,3,4,6-TETRA-O-BENZYL-ALPHA-D-GLUCOPYRANOSE Usage And Synthesis
- 5. 2,3,4,6-TETRA-O-BENZYL-ALPHA-D-GLUCOPYRANOSE Preparation Products And Raw materials
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);Voglibose int;Voglibose Impurity 1;2,3,4,6-Tetra-O-benzyl-D-glycopyranose;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 |
| 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 |
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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 |
| form | Solid |
| pka | 11.87±0.70(Predicted) |
| color | White to off-white |
| Water Solubility | Soluble in CHCl3. Insoluble in water. |
| InChIKey | OGOMAWHSXRDAKZ-DLANKZEINA-N |
| SMILES | O([C@@H]1[C@H]([C@@H](O)O[C@H](COCC2C=CC=CC=2)[C@H]1OCC1C=CC=CC=1)OCC1C=CC=CC=1)CC1C=CC=CC=1 |&1:1,2,3,6,16,r| |
| LogP | 5.9 at 20℃ and pH6.5 |
| CAS DataBase Reference | 6564-72-3(CAS DataBase Reference) |
Safety Information
| Safety Statements | 22-24/25 |
| WGK Germany | 3 |
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
