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

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

Codice CAS
87-91-2
Sinonimi
L-Tartaric acid diethyl ester

Dimensioni Prezzo ($) Quantità Disponibilità
100g 38,20
250g 84,30
500g 151,00
1000g 245,00
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(+)-Diethyl L-tartrate, 98%

MDL
MFCD00009143
EINECS
201-783-3

Proprietà chimiche

Formula
C8H14O6
Peso formula
206.19
Punto di fusione
17°
Punto di ebollizione
280°
Punto di infiammabilità
93°(199°F)
Densità
1.205
Indice di rifrazione
1.4460
Solubilità
Fully miscible in water.

Applicazioni

(+)-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.

Note

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

Letteratura

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).

Rischio GHS e dichiarazioni precauzionali

Dichiarazioni di rischio (UE): H227

Combustible liquid.

Dichiarazioni precauzionali: P210u-P280a-P370+P378a-P403+P235-P501a

Wear protective gloves and eye/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.

Altri riferimenti

Merck
14,3855
Beilstein
1727145
Codice tariffe armonizzato
2918.13
TSCA
Yes

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