Diethyl tartrate

Diethyl tartrate

Names
Preferred IUPAC name Diethyl 2,3-dihydroxybutanedioate
Other names Diethyl 2,3-dihydroxysuccinate
Identifiers
CAS Number	408332-88-7  Y 87-91-2 (R,R)-(+)-L 13811-71-7 (S,S)-(−)-D 57968-71-5 (D/L) 21066-72-8 meso
3D model (JSmol)	Interactive image
ChemSpider	104927  Y
PubChem CID	62333
UNII	OQ72CPY58Z  (R,R)-(+)-L Y
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 Y Key: YSAVZVORKRDODB-WDSKDSINSA-N Y 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	Colorless liquid
Density	1.204 g/mL
Melting point	17 °C (63 °F; 290 K)
Boiling point	280 °C (536 °F; 553 K)
Solubility in water	low
Magnetic susceptibility (χ)	−113.4·10−6 cm3/mol
Hazards
Safety data sheet (SDS)	Diethyl D-Tartrate MSDS
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

Diethyl tartrate is an organic compound with the formula (HOCHCO₂Et)₂ (Et = ethyl). Three stereoisomers exist, R,R-, S,S-, and R,S (=S,R-). They are the ethyl esters of the respective R,R-, S,S-, and R,S-tartaric acids. The R,R- and S,S- isomers are enantiomeric, being mirror images. The meso stereoisomer 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] The TADDOL ligand scaffold is produced from diethyl tartrate. ^[2]

References

1. Hill, J. Gordon; Sharpless, K. Barry; Exon, Christopher M.; Regenye, Ronald (1985). "Enantioselective Epoxidation of Allylic Alcohols: (2S,3S)-3-Propyloxiranemethanol". Organic Syntheses. 63: 66. doi:10.15227/orgsyn.063.0066.
2. Henrik Teller, Susanne Flügge, Richard Goddard, Alois Fürstner (2010). "Enantioselective Gold Catalysis: Opportunities Provided by Monodentate Phosphoramidite Ligands with an Acyclic TADDOL Backbone". Angew. Chem. Int. Ed. 49 (11): 1949–1953. doi:10.1002/anie.200906550. PMID   20175172.