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
CAS Number	13265-84-4 ;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL2115567;
ChemSpider	2016480 ;
ECHA InfoCard	100.032.949
EC Number	236-259-3;
PubChem CID	2734736;
CompTox Dashboard (EPA)	DTXSID60157685 ;
	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
	GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H315, H319, H335
Precautionary statements	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). verify (what is ?) 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.^[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.

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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
CAS Number	13265-84-4^Y
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL2115567
ChemSpider	2016480^Y
ECHA InfoCard	100.032.949
EC Number	236-259-3
PubChem CID	2734736
CompTox Dashboard (EPA)	DTXSID60157685
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^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
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
GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H315, H319, H335
Precautionary statements	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). Y verify (what is ^YN ?) Infobox references