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A10641 (+)-Diethyl L-tartrate, 98%

CAS Number
87-91-2
Synonyms
L-Tartaric acid diethyl ester

Stock No. Size Price ($) Quantity Availability
A10641-22 100g 40.60
A10641-30 250g 87.30
A10641-36 500g 158.00
A10641-0B 1000g 252.00
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(+)-Diethyl L-tartrate, 98%

MDL
MFCD00009143
EINECS
201-783-3

Chemical Properties

Formula
C8H14O6
Formula Weight
206.19
Melting point
17°
Boiling Point
280°
Flash Point
93°(199°F)
Density
1.205
Refractive Index
1.4460
Storage & Sensitivity
Ambient temperatures.
Solubility
Fully miscible in water.

Applications

(+)-Diethyl L-tartrate is used as a chiral auxiliary in the Sharpless enantioselective epoxidation of allylic alcohols, for Sharpless-type enantioselective oxidation of sulfides to sulfoxides and as a chiral auxiliary in the enantioselective construction of cyclopropanes from allylic alcohols by an asymmetric Simmons-Smith reaction. It is also used as a chiral reagent in a host of chemical reactions, such as the synthesis of isoquinoline alkaloids and arundic acid, which has been used in acute ischemic stroke therapy.

Notes

Keep container tightly sealed. Store in cool, dry conditions in well sealed containers. Incompatible with oxidizing agents.

Literature References

Peter Somfai. An enantioselective total synthesis of (+)-altholactone from diethyl L-tartrate. Tetrahedron. 1994, 50, (38), 11315-11320.

Woo-Wha Lee.; Sukbok Chang. A new and concise synthetic route to an enantiopure (+)-conduritol-E derivative from diethyl l-tartrate. Tetrahedron: Asymmetry. 1999, 10 (23), 4473-4475.

For use as a chiral auxiliary in the Sharpless enantioselective epoxidation of allylic alcohols, see tert-Butyl­ hydroperoxide, A13926. For Sharpless-type enantioselective oxidation of sulfides to sulfoxides, see: Org. Synth. Coll., 8, 464 (1993).

For use as a chiral auxiliary in the enantioselective construction of cyclopropanes from allylic alcohols by an asymmetric Simmons-Smith reaction, see: Chem. Lett., 61 (1992). For a review of the use of tartrate esters as chiral auxiliaries, e.g. in the Simmons-Smith reaction and in 1,3-dipolar cycloaddition reactions, see: Synlett, 1075 (2003).

GHS Hazard and Precautionary Statements

Hazard Statements: H227-H315-H319

Combustible liquid. Causes skin irritation. Causes serious eye irritation.

Precautionary Statements: P210-P264b-P280-P302+P352-P305+P351+P338-P332+P313-P337+P313-P362-P370+P378q-P501c

Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Wash face, hands and any exposed skin thoroughly after handling Wear protective gloves/protective clothing/eye protection/face protection. IF ON SKIN: Wash with plenty of soap and water. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. If skin irritation occurs: Get medical advice/attention. If eye irritation persists: Take off contaminated clothing and wash before reuse. In case of fire: Use CO2, dry chemical, or foam Dispose of contents/ container to an approved waste disposal plant

Other References

Merck
14,3855
Beilstein
1727145
Harmonized Tariff Code
2918.13
TSCA
Yes

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