21193-75-9
D-galactal
CAS: 21193-75-9
Molecular Formula: C6H10O4
21193-75-9 - Names and Identifiers
| Name | D-galactal |
| Synonyms | GALACTAL D-Galactat D-galactal D-GALACTAL GALACTAL, D- 1,5-anhydro-2-deoxyhex-1-enitol 1,5-ANHYDRO-2-DEOXY-D-LYXO-HEX-1-ENITOL 2,6-anhydro-5-deoxy-D-arabino-hex-5-enitol 2-(Hydroxymethyl)-3,4-dihydro-2H-pyran-3,4-diol (2R)-2α-(Hydroxymethyl)-3,4-dihydro-2H-pyran-3α,4α-diol (2R,3R,4R)-2-(hydroxymethyl)-3,4-dihydro-2H-pyran-3,4-diol |
| CAS | 21193-75-9 |
| EINECS | 244-264-7 |
| InChI | InChI=1/C6H10O4/c7-3-5-6(9)4(8)1-2-10-5/h1-2,4-9H,3H2/t4-,5-,6-/m1/s1 |
| InChIKey | YVECGMZCTULTIS-HSUXUTPPSA-N |
21193-75-9 - Physico-chemical Properties
| Molecular Formula | C6H10O4 |
| Molar Mass | 146.14 |
| Density | 1.414±0.06 g/cm3(Predicted) |
| Melting Point | 99-103 °C (lit.) |
| Boling Point | 325.5±42.0 °C(Predicted) |
| Flash Point | 150.7°C |
| Solubility | Acetonitrile (Slightly), Methanol (Slightly) |
| Vapor Presure | 1.77E-05mmHg at 25°C |
| Appearance | White powder |
| Color | White to Off-White |
| BRN | 81690 |
| pKa | 12.79±0.60(Predicted) |
| Storage Condition | 2-8°C |
| Stability | Moisture Sensitive |
| Refractive Index | -22 ° (C=1.2, MeOH) |
| MDL | MFCD00038067 |
| Use | Important block for solution and liquid-solid synthesis of oligosaccharides. |
21193-75-9 - Risk and Safety
| Hazard Symbols | Xi - Irritant |
| Risk Codes | 36/37/38 - Irritating to eyes, respiratory system and skin. |
| Safety Description | S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S36 - Wear suitable protective clothing. S24/25 - Avoid contact with skin and eyes. |
| WGK Germany | 3 |
| HS Code | 29329990 |
21193-75-9 - Reference Information
| Overview | D-galactoene is also called perhydroxygalactoene. It can be prepared from D-galactose in four steps. It can be used to prepare glycosyl donor 3, 4-O-isopropylidene-6-O-tert-butyldiphenylsilyl-D-galactoene. |
| preparation | specifically includes the following steps:(1) weighing D-galactose (20.0g,55.5mmol) according to stoichiometric ratio and adding it into a round bottom flask (500ml), then adding anhydrous sodium acetate (4.0g 48.8mmol) and acetic anhydride (40.0ml) under reflux reaction for 2 hours, the reaction is judged to be complete by thin layer chromatography (petroleum ether: ethyl acetate = 3:1), after the system is cooled, pour it into ice water and stir (300r /min, the same below) to remove acetic anhydride, and then filter under reduced pressure to obtain solid products. After washing with water for three times, wash with absolute ethanol once, finally, the solid product obtained by vacuum suction filtration was dried at 50 ℃ for 12 hours to obtain product compound a (peracetylgalactose)(36.1g,79.7mmol) with a yield of 83.2%. (2) Compound A (10.0g,25.6mmol) is added into a 250ml round-bottom flask, dry dichloromethane (50.0ml) is added, stirred to dissolve it in an ice bath, and then 33% hydrogen bromide acetic acid solution (HBr-CH3COOH) is added dropwise under shading conditions. After the reaction is completed for 2h, the reaction is judged to be complete by thin layer chromatography (petroleum ether: ethyl acetate = 3:1), and the system is diluted with dichloromethane, then add saturated NaHCO3 solution to neutralize the system to neutral one by one, retain the organic layer after stratification, extract the water layer twice with dichloromethane, merge the organic layer, wash the organic layer with saturated salt water, dry the organic layer with anhydrous sodium sulfate, and remove the excess solvent under reduced pressure distillation (-0.09MPa,45 ℃) to spin and dry to obtain light yellow slurry product compound B (total acetyl-galactosaccharide)(9.2g,22.3mmol), the yield is 87.1%. (3) under the condition of ice salt bath, compound B (9.2g,22.3mmol) is added into the system of zinc powder (10.4g,160.6mmol) and 50% acetic acid solution (56.5ml) for 4h, and the reaction is completely determined by thin layer chromatography (petroleum ether: ethyl acetate = 3:1). after the reaction, dichloromethane is added into the system for dilution, and then the zinc powder is removed by vacuum filtration, add saturated sodium bicarbonate solution to the filtrate one by one, adjust the pH to neutral, retain the organic layer in the liquid, extract the water layer twice with dichloromethane, merge the organic layers, wash the organic layer once with saturated salt aqueous solution, dry with anhydrous sodium sulfate, and remove the excess solvent by vacuum distillation (-0.09MPa,45 ℃) to spin and dry to obtain light yellow slurry product compound C (all acetylgalactol sugar)(5.5g,20.2mmol), the yield is 91.6%. (4) Add the crude product compound C (5.5g,20.2mmol) obtained in the previous step into a round bottom flask (250ml), then add methanol (84.0ml) to it, stir to dissolve it, then add sodium methoxide (0.55g,10.2mmol), react at room temperature for 1-2h, and remove acetic acid group (Ac) by reaction at room temperature. The reaction is complete by thin layer chromatography (dichloromethane: methanol = 10:1) After the reaction is complete, acetic acid is added to adjust the pH to neutral or weakly alkaline, and the excess solvent is removed by reduced pressure distillation (-0.09MPa,45 ℃) to spin dry to obtain the crude yellowish slurry product. The important intermediate compound D (D-galactoene)(2.7g,18.5mmol) is obtained by silica gel column chromatography separation (dichloromethane: methanol = 5:1) with a yield of 77.1%. |
| use | important block for solution and liquid-solid synthesis of oligosaccharides. |
Last Update：2024-04-09 20:52:54
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