D-arabino-Hex-1-enitol, 1,5-anhydro-2-deoxy-
D-glucal
CAS: 13265-84-4
Molecular Formula: C6H10O4
D-arabino-Hex-1-enitol, 1,5-anhydro-2-deoxy- - Names and Identifiers
D-arabino-Hex-1-enitol, 1,5-anhydro-2-deoxy- - Physico-chemical Properties
| Molecular Formula | C6H10O4 |
| Molar Mass | 146.14 |
| Density | 1.414±0.06 g/cm3(Predicted) |
| Melting Point | 58-60 °C (lit.) |
| Boling Point | 325.5±42.0 °C(Predicted) |
| Flash Point | 150.7°C |
| Solubility | Soluble in Methanol. |
| Vapor Presure | 1.77E-05mmHg at 25°C |
| Appearance | White crystal |
| Color | White |
| pKa | 12.79±0.60(Predicted) |
| Storage Condition | 2-8°C |
| Sensitive | Moisture Sensitive |
| Refractive Index | -10 ° (C=2, H2O) |
| MDL | MFCD09039277 |
| Use | An important intermediate for the synthesis of oligosaccharides by solid phase method. |
D-arabino-Hex-1-enitol, 1,5-anhydro-2-deoxy- - Risk and Safety
| Risk Codes | R21 - Harmful in contact with skin R36/38 - Irritating to eyes and skin. R46 - May cause heritable genetic damage R62 - Possible risk of impaired fertility R63 - Possible risk of harm to the unborn child R36/37/38 - Irritating to eyes, respiratory system and skin. |
| Safety Description | S22 - Do not breathe dust. S24/25 - Avoid contact with skin and eyes. S53 - Avoid exposure - obtain special instructions before use. S36/37 - Wear suitable protective clothing and gloves. S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S25 - Avoid contact with eyes. S36 - Wear suitable protective clothing. |
| WGK Germany | 3 |
| HS Code | 29339900 |
D-arabino-Hex-1-enitol, 1,5-anhydro-2-deoxy- - Reference Information
| Introduction | D-glucosaccharide, also known as D-glucosene, is a pharmaceutical intermediate that can be prepared from pentaacetyl glucose through a three-step reaction. D-glucosaccharide can be used to prepare fluoroglycosyl modified paclitaxel compounds. |
| Preparation | 2,3, 4,6-tetra-acetyl-1-bromo-α-D-glucopyranose (9) Preparation: Compound 8 (pentaacetyl glucose)(10g,25.6mmol) is dissolved in anhydrous dichloromethane (60mL). Under ice bath conditions, hydrogen bromide acetic acid (33%, mass%) solution (4.9mL,2.0equiv.) was slowly added to it. Chamber Temperature reaction for 6 hours. After the detection reaction is completed, the ice solution of saturated sodium bicarbonate is added to the reaction system to quench the reaction, and the two-phase extraction is made with dichloro methane and water to obtain oily compound 9(10.1g, yield 96%, mass percentage) Rf0.6(PE/EA2/1), which is directly used in the next step. Preparation of 3,4, 6-tris-acetyl-glucoene (10): Compound 9(5g,12.16mmol) was dissolved in acetone, zinc powder (7.63g,9.6equiv.) and saturated NaH2PO4 solution (30mL) were added at room temperature. Reaction at room temperature for 12 hours. After that, filtration, extraction with dichloromethane and saturated NaHCO3 solution, anhydrous Na2SO4 drying, spin-evaporation concentration to obtain oily compound 10(3.1g, yield 94%, mass percentage), Rf0.3(PE/EA5/1), which is directly used for the next step. Preparation of D-glucosene (11): at room temperature, MeONa(158.75mg,2.94 mmol,0.4equiv.) is added to the methanol solution (15mL) of compound 10(2g,7.35mmol) for 1.5 hours. after the reaction is completed, h ion exchange resin is used to adjust the pH to 7.0, filter, and is rotated to evaporate and concentrate to obtain oily compound 11(1g, 93% yield, mass percentage). |
| use | an important intermediate for solid phase synthesis of oligosaccharides. |
Last Update：2024-04-09 21:54:55
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