Diethyl tartrate

Diethyl tartrate
	Skeletal formula of diethyl tartrate
Names
	Preferred IUPAC name Diethyl 2,3-dihydroxybutanedioate
	Other names Diethyl 2,3-dihydroxysuccinate
Identifiers
CAS Number	87-91-2 ;
3D model (JSmol)	Interactive image;
ChemSpider	104927 ;
PubChem CID	62333;
CompTox Dashboard (EPA)	DTXSID70859148 ;
	InChI InChI=1S/C8H14O6/c1-3-13-7(11)5(9)6(10)8(12)14-4-2/h5-6,9-10H,3-4H2,1-2H3/t5-,6-/m0/s1 Key: YSAVZVORKRDODB-WDSKDSINSA-N ; InChI=1/C8H14O6/c1-3-13-7(11)5(9)6(10)8(12)14-4-2/h5-6,9-10H,3-4H2,1-2H3/t5-,6-/m0/s1 Key: YSAVZVORKRDODB-WDSKDSINBN;
	SMILES O=C(OCC)[C@@H](O)[C@H](O)C(=O)OCC;
Properties
Chemical formula	C8H14O6
Molar mass	206.194 g·mol−1
Appearance	colourless
Density	1.204 g/mL
Boiling point	280 °C (536 °F; 553 K)
Solubility in water	low
	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

Diethyl tartrate is an organic compound, the ethyl ester of tartaric acid. It exists in both as a chiral isomer, showing both left- and right-handed forms, as well as a meso stereoisomer, which is not chiral. The chiral isomer is far more common.

In the Sharpless epoxidation, diethyl tartrate and titanium isopropoxide form a chiral catalyst in situ.^[1]

References

^ J. Gordon Hill, K. Barry Sharpless, Christopher M. Exon, and Ronald Regenye (1985). "Enantioselective Epoxidation of Allylic Alcohols: (2S,3S)-3-Propyloxiranemethanol". Organic Syntheses. 63: 66{{cite journal}}: CS1 maint: multiple names: authors list (link); Collected Volumes, vol. 7, p. 461.

[1] J. Gordon Hill, K. Barry Sharpless, Christopher M. Exon, and Ronald Regenye (1985). "Enantioselective Epoxidation of Allylic Alcohols: (2S,3S)-3-Propyloxiranemethanol". Organic Syntheses. 63: 66{{cite journal}}: CS1 maint: multiple names: authors list (link); Collected Volumes, vol. 7, p. 461.

[1]