Glucal[1] |
Names |
IUPAC name (2R,3S,4R)-2-(Hydroxymethyl)-3,4-dihydro-2H-pyran-3,4-diol |
Identifiers |
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3D model (JSmol) | |
ChemSpider | |
ECHA InfoCard | 100.032.949 |
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InChI=1S/C6H10O4/c7-3-5-6(9)4(8)1-2-10-5/h1-2,4-9H,3H2/t4-,5-,6+/m1/s1  Key: YVECGMZCTULTIS-PBXRRBTRSA-N  InChI=1/C6H10O4/c7-3-5-6(9)4(8)1-2-10-5/h1-2,4-9H,3H2/t4-,5-,6+/m1/s1 Key: YVECGMZCTULTIS-PBXRRBTRBT |
SMILES C1=CO[C@@H]([C@H]([C@@H]1O)O)CO |
Properties |
| C6H10O4 |
Molar mass | 146.1412 |
Melting point | 58 to 60 °C (136 to 140 °F; 331 to 333 K) |
Hazards |
S-phrases (outdated) | S22 S24/25 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). |
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Glucal is the glycal formed from glucose.[2] It is a chemical intermediate in the synthesis of a variety of oligosaccharides.[3]
Glucal and its derivatives can be converted to other chemically useful sugars using the Ferrier rearrangement.
References
- ^ Glucal at Sigma-Aldrich
- ^ E.Fischer and K. Zasch. Sitzber. kgl.preuss. Akad Wiss., 16,311 (1913)
- ^ Seeberger, P.H., et al. Aldrichimica Acta 30, 75, (1997)
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