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213969

Sigma-Aldrich

(−)-Diethyl D-tartrate

≥99%

Synonym(s):

D-(−)-Tartaric acid diethyl ester

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About This Item

Linear Formula:
HO2CCCH(OH)CH(OH)CO2H
CAS Number:
13811-71-7
Molecular Weight:
206.19
Beilstein:
1727143
EC Number:
237-458-8
MDL number:
MFCD00064451
UNSPSC Code:
12352108
PubChem Substance ID:
24852814
NACRES:
NA.22

Assay

≥99%

optical activity

[α]23/D −8.5°, neat

optical purity

ee: ≥99% (GLC)

refractive index

n20/D 1.446 (lit.)

bp

162 °C/19 mmHg (lit.)

density

1.205 g/mL at 20 °C (lit.)

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-/m0/s1

InChI key

YSAVZVORKRDODB-WDSKDSINSA-N

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Application

(-)-Diethyl D-tartrate can be used as a starting material in the synthesis of bioactive compounds such as (-)-kumausallene, syringolide 2 and (+)-exo-brevicomin.

Storage Class Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

200.1 °F - closed cup

Flash Point(C)

93.4 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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A new expeditious synthesis of (+)-exo-brevicomin via efficient C? C bond formation of triflates.
Kotsuki H, et al.
Tetrahedron Letters, 30(30), 3999-4000 (1989)
Radical cyclization of ?-alkoxyacrylates: A formal synthesis of (-)-kumausallene.
Lee E, et al.
Tetrahedron Letters, 39(3), 317-318 (1998)
Synthesis and absolute configuration of syringolide 2, an elicitor from Pseudomonas syringae pv. tomato.
Kuwahara S, et al.
Tetrahedron Letters, 36(18), 3201-3202 (1995)
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
Naoto Hama et al.
Organic letters, 13(4), 616-619 (2011-01-05)
A first total synthesis of broussonetine F from diethyl L-tartrate was achieved. The cornerstone of our synthesis was an orthoamide Overman rearrangement, which provided an allylic amino alcohol with complete diastereoselectivity.
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