Glucal

Glucal is the glycal formed from glucose.[2] It is a chemical intermediate in the synthesis of a variety of oligosaccharides.[3]

Glucal[1]
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
ECHA InfoCard 100.032.949
EC Number
  • 236-259-3
  • InChI=1S/C6H10O4/c7-3-5-6(9)4(8)1-2-10-5/h1-2,4-9H,3H2/t4-,5-,6+/m1/s1 checkY
    Key: YVECGMZCTULTIS-PBXRRBTRSA-N checkY
  • 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
  • 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
GHS labelling:
GHS07: Exclamation mark
Warning
H315, H319, H335
P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)
Infobox references

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)


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