213969
(−)-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:
Molecular Weight:
206.19
UNSPSC Code:
12352108
NACRES:
NA.22
PubChem Substance ID:
EC Number:
237-458-8
Beilstein/REAXYS Number:
1727143
MDL number:
Assay:
≥99%
Quality Level
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.)
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-/m0/s1
InChI key
YSAVZVORKRDODB-WDSKDSINSA-N
Related Categories
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
10 - Combustible liquids
wgk
WGK 3
flash_point_f
200.1 °F - closed cup
flash_point_c
93.4 °C - closed cup
ppe
Eyeshields, Gloves
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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)
Naoki Miyakoshi et al.
The Journal of organic chemistry, 70(15), 6045-6052 (2005-07-16)
A highly stereoselective method for constructing a (2E)-methoxymethylidene-1,6-dioxaspiro[4.5]decane skeleton has been developed on the basis of the palladium(II)-catalyzed ring-closing reaction of the 3,4-dioxygenated-9-hydroxy-1-nonyn-5-one derivatives as a crucial step. The newly developed procedures could be successfully applied to the first total
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.
Global Trade Item Number
| SKU | GTIN |
|---|---|
| 213969-500G | 04061837639098 |
| 213969-5G | 04061837639104 |
| 213969-25G | 04061838773029 |
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