Glucal

Glucal^[1]

Names
IUPAC name (2R,3S,4R)-2-(Hydroxymethyl)-3,4-dihydro-2H-pyran-3,4-diol
Identifiers
CAS Number	13265-84-4
3D model (Jmol)	Interactive image
ChemSpider	2016480
ECHA InfoCard	100.032.949
PubChem	2734736
InChI 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
Chemical formula	C6H10O4
Molar mass	146.1412
Melting point	58 to 60 °C (136 to 140 °F; 331 to 333 K)
Hazards
S-phrases	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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Infobox references

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

1. Glucal at Sigma-Aldrich
2. E.Fischer and K. Zasch. Sitzber. kgl.preuss. Akad Wiss., 16,311 (1913)
3. Seeberger, P.H., et al. Aldrichimica Acta 30, 75, (1997)