Diisopropyl tartrate

Diisopropyl tartrate
Names


IUPAC name Diisopropyl tartrate
Other names Bis(1-methylethyl) ester of 2,3-dihydroxybutanedioic acid, Dipropan-2-yl 2,3-dihydroxybutanedioate, DIPT
Identifiers
CAS Number	2217-15-4^Y
ChemSpider	101254 (−)-isomer^N
EC Number	218-709-0
Jmol interactive 3D	(−)-isomer: Image Image
PubChem	102768 (−)-isomer 112972
InChI (−)-isomer: InChI=1S/C10H18O6/c1-5(2)15-9(13)7(11)8(12)10(14)16-6(3)4/h5-8,11-12H,1-4H3/t7-,8-/m0/s1^N Key: XEBCWEDRGPSHQH-YUMQZZPRSA-N^N
SMILES (−)-isomer: CC(C)OC(=O)C(C(C(=O)OC(C)C)O)O O=C(OC(C)C)[C@@H](O)[C@H](O)C(=O)OC(C)C
Properties
Chemical formula	C₁₀H₁₈O₆
Molar mass	234.25 g/mol
Boiling point	152 °C (306 °F; 425 K) at 16 kPa
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is ^YN ?)
Infobox references

Diisopropyl tartrate (DIPT) is a diester of tartaric acid. It has a two chiral carbon atoms giving rise to three stereoisomeric variants. It is commonly used in asymmetric synthesis as a catalyst and as chiral building block for pharmaceuticals and agrochemicals. Its main application is in Sharpless epoxidation, where it serves as a chiral ligand to titanium after reaction with titanium isopropoxide.^[1]

References

↑ Katsuki, Tsutomu; Sharpless, K. Barry (1980). "The first practical method for asymmetric epoxidation". J. Am. Chem. Soc. 102 (18): 5974. doi:10.1021/ja00538a077.

This article is issued from Wikipedia - version of the Monday, November 16, 2015. The text is available under the Creative Commons Attribution/Share Alike but additional terms may apply for the media files.