Cookies disclaimer

I agree Our site saves small pieces of text information (cookies) on your device in order to deliver better content and for statistical purposes. You can disable the usage of cookies by changing the settings of your browser. By browsing our website without changing the browser settings you grant us permission to store that information on your device.

87-91-2 - (+)-Diethyl L-tartrate, 98% - L-Tartaric acid diethyl ester - A10641 - Alfa Aesar

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

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

Size Price ($) Quantity Availability
100g 38.63
250g 88.58
500g 138.60
1000g 225.00
Add to Cart Add to Quote Request View Item

(+)-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
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

Combustible liquid.

Precautionary Statements: P210-P280-P370+P378a-P403+P235-P501a

Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Wear protective gloves/protective clothing/eye protection/face protection. In case of fire: Use for extinction: CO2, powder or water spray. Store in a well-ventilated place. Keep cool. Dispose of contents/container in accordance with local/regional/national/international regulations.

Other References

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

Recommended

Recently Viewed

Chemicals

Life Science

Metals & Materials

Catalysts

Analytical & Labware