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156841

Sigma-Aldrich

(+)-Diethyl L-tartrate

≥99%

Synonym(s):

L-(+)-Tartaric acid diethyl ester

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About This Item

Linear Formula:
[-CH(OH)CO2C2H5]2
CAS Number:
87-91-2
Molecular Weight:
206.19
Beilstein/REAXYS Number:
1727145
EC Number:
201-783-3
MDL number:
MFCD00009143
UNSPSC Code:
12352108
PubChem Substance ID:
24849640
NACRES:
NA.22

assay

≥99%

optical activity

[α]20/D +8.5°, neat

optical purity

ee: ≥99% (GLC)

refractive index

n20/D 1.446 (lit.)

bp

280 °C (lit.)

density

1.204 g/mL at 25 °C (lit.)

functional group

ester
hydroxyl

SMILES string

CCOC(=O)[C@H](O)[C@@H](O)C(=O)OCC

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-/m1/s1

InChI key

YSAVZVORKRDODB-PHDIDXHHSA-N

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General description

Made from natural tartaric acid

Application

(+)-Diethyl L-tartrate can be used in the synthesis of biologically active compounds such as (+)-altholactone, (-)-aspicilin, (+)-monomorine I and (+)-(1R,2R,3S,6S)-3,6-di-O-methyl conduritol-E.

pictograms

Exclamation mark
GHS07

signalword

Warning

hcodes

H319

Hazard Classifications

Eye Irrit. 2

Storage Class

10 - Combustible liquids

wgk_germany

WGK 3

flash_point_f

199.4 °F - closed cup

flash_point_c

93 °C - closed cup

ppe

Eyeshields, Gloves, type ABEK (EN14387) respirator filter

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Certificates of Analysis (COA)

Lot/Batch Number
STBK4972
STBK2415
STBJ2427
STBH8163
STBG4024V

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Enantioselective total synthesis of (+)-monomorine I.
Yamazaki N and Kibayashi C.
Tetrahedron Letters, 29(45), 5767-5768 (1988)
An enantioselective total synthesis of (+)-altholactone from diethyl L-tartrate.
Somfai P.
Tetrahedron, 50(38), 11315-11320 (1994)
A new and concise synthetic route to an enantiopure (+)-conduritol-E derivative from diethyl l-tartrate.
Lee WW and Chang S.
Tetrahedron Asymmetry, 10(23), 4473-4475 (1999)
Stereocontrolled total synthesis of the macrocyclic lactone (-)-aspicilin.
Waanders PP, et al.
Tetrahedron Letters, 28(21), 2409-2412 (1987)
Kimberly A Kahle et al.
Electrophoresis, 28(15), 2644-2657 (2007-06-29)
In this second study on dual-chirality microemulsions containing a chiral surfactant and a chiral oil, a less hydrophobic and lower interfacial tension chiral oil, diethyl tartrate, is employed (Part 1, Foley, J. P. et al.., Electrophoresis, DOI: 10.1002/elps.200600551). Six stereochemical
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