2,3,4,6-TETRA-O-BENZOYL-D-GLUCOPYRANOSE
2,3,4,6-tetra-O-benzyl-D-glucopyranose
CAS: 6564-72-3;4132-28-9
Molecular Formula: C34H36O6
2,3,4,6-TETRA-O-BENZOYL-D-GLUCOPYRANOSE - Names and Identifiers
| Name | 2,3,4,6-tetra-O-benzyl-D-glucopyranose |
| Synonyms | Voglibose int benzylglucopyranose Voglibose Impurity 1 2,3,4,6-Tetra-O-benzyl-D-glucofuranose 2,3,4,6-tetra-O-benzyl-D-glucopyranose 2,3,4,6-Tetra-O-benzyl-alpha-D-glucose 2,3,4,6-Tetra-O-benzyl-D-glycopyranose 2,3,4,6-TETRA-O-BENZOYL-D-GLUCOPYRANOSE 2,3,4,6-TETRA-O-BENZYL-D-GLUCOPYRANOSIDE 2,3,4,6-Tetra-O-benzyl-alpha-D-glucose (for Voglibose) |
| CAS | 6564-72-3 4132-28-9 |
| EINECS | 667-304-9 |
| InChI | InChI=1/C34H36O6/c35-34-33(39-24-29-19-11-4-12-20-29)32(38-23-28-17-9-3-10-18-28)31(37-22-27-15-7-2-8-16-27)30(40-34)25-36-21-26-13-5-1-6-14-26/h1-20,30-35H,21-25H2/t30-,31-,32+,33-,34?/m1/s1 |
2,3,4,6-TETRA-O-BENZOYL-D-GLUCOPYRANOSE - Physico-chemical Properties
| Molecular Formula | C34H36O6 |
| Molar Mass | 540.66 |
| Density | 1.22 |
| Melting Point | 151-156°C |
| Boling Point | 672.4±55.0 °C(Predicted) |
| Flash Point | 360.441°C |
| Water Solubility | Soluble in CHCl3. Insoluble in water. |
| Vapor Presure | 0mmHg at 25°C |
| Appearance | Crystalline powder |
| pKa | 11.87±0.70(Predicted) |
| Storage Condition | Sealed in dry,Store in freezer, under -20°C |
| Refractive Index | 1.619 |
| MDL | MFCD00066004 |
| Use | D-glucopyranose derivatives are important for glycosylation and other reactions. Preparation of glucopyranose chloride; Synthesis of 1-C-α-D-glucopyranose derivatives. |
2,3,4,6-TETRA-O-BENZOYL-D-GLUCOPYRANOSE - Risk and Safety
| Safety Description | S22 - Do not breathe dust. S24/25 - Avoid contact with skin and eyes. |
| WGK Germany | 3 |
2,3,4,6-TETRA-O-BENZOYL-D-GLUCOPYRANOSE - Reference Information
| LogP | 5.9 at 20℃ and pH6.5 |
| Overview | 2,3,4, 6-tetra-o-benzyl-d-glucopyranose is a kind of pharmaceutical intermediate of glucose, which can be prepared from α-Methyl glucoside by two-step reaction. |
| Application | 2,3,4, 6-tetra-o-benzyl-d-glucopyranose is useful in the preparation of SGLT2 inhibitors and is a key intermediate in the preparation of SGLT2 inhibitors. |
| preparation method | preparation of intermediate D-3: 25g of compound D-2 were dissolved in 500mL DMF, 52g of 60% sodium hydride was added at 0 ° C., and 92mL of benzyl bromide was added after 1H of reaction, followed by overnight reaction at room temperature. Saturated ammonium chloride solution quenching, ethyl acetate extraction, saturated sodium chloride solution washing, anhydrous sodium sulfate drying. Under reduced pressure evaporation silica gel column chromatography to give colorless oil compound D-3 67G, yield 94%. Preparation of intermediate D-4(2,3,4, 6-tetra-o-benzyl-d-glucopyranose): 60g of compound D-3 was dissolved in of glacial acetic acid, then, 126ml of 1N sulfuric acid was added thereto, and the mixture was refluxed for 2H and then evaporated to dryness under reduced pressure to give 57g of a white solid compound D-4 in a yield of 97%. |
Last Update：2024-04-09 20:49:11
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