Chemistry:Glucal

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Glucal[1]
Glucal.svg
Names
IUPAC name
1,5-Anhydro-2-deoxy-D-arabino-hex-1-enitol
Systematic IUPAC name
(2R,3S,4R)-2-(Hydroxymethyl)-3,4-dihydro-2H-pyran-3,4-diol
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
EC Number
  • 236-259-3
Properties
C6H10O4
Molar mass 146.1412
Melting point 58 to 60 °C (136 to 140 °F; 331 to 333 K)
Hazards
GHS pictograms GHS07: Harmful
GHS Signal word Warning
H315, H319, H335
P261, P264, P271, P280, P302+352, P304+340, P305+351+338, P312, P321, P332+313, P337+313, P362, P403+233, P405, P501
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
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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

  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)