Glucal
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
ChEMBL
ChemSpider
ECHA InfoCard
100.032.949
EC Number
InChI=1S/C6H10O4/c7-3-5-6(9)4(8)1-2-10-5/h1-2,4-9H,3H2/t4-,5-,6+/m1/s1
Y Key: YVECGMZCTULTIS-PBXRRBTRSA-N
Y 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
C6 H10 O4
Molar mass
146.1412
Melting point
58 to 60 °C (136 to 140 °F; 331 to 333 K)
Hazards
GHS labelling :
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).
Chemical compound
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 .[ 4]
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)
^ Ferrier, Robert J. (2001). "Substitution-with-Allylic-Rearrangement Reactions of Glycal Derivatives". Glycoscience . Topics in Current Chemistry. Vol. 215. pp. 153–175. doi :10.1007/3-540-44422-X_7 . ISBN 978-3-540-41383-7 .