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608-68-4 - Dimethyl L-tartrate, 99% - L-Tartaric acid dimethyl ester - L06561 - Alfa Aesar

L06561 Dimethyl L-tartrate, 99%

CAS Number
608-68-4
Synonyms
L-Tartaric acid dimethyl ester

Size Price ($) Quantity Availability
25g 22.20
100g 52.70
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Dimethyl L-tartrate, 99%

MDL
MFCD00064437
EINECS
210-166-8

Chemical Properties

Formula
C6H10O6
Formula Weight
178.14
Melting point
56-61°
Boiling Point
158°/11mm
Flash Point
>170°(338°F)
Density
1.30
Solubility
Soluble in water.

Applications

Dimethyl L-tartrate is a chiral auxiliary used for the enantioselective epoxidation of allylic alcohols. It is used for asymmetric α-halogenation of acetals. It is a starting material for the synthesis of chiral building blocks.

Notes

Stable under recommended storage conditions. Incompatible with oxidizing agents.

Literature References

Nobuo Nagashima; Masaji Ohno. An efficient O-monoalkylation of dimethyl L-tartrate via O-stannylene acetal with alkyl halides in the presence of cesium fluoride. Chemistry Letters. 1987, 16,(1), 141-144.

 

Thierry Buffeteau; Laurent Ducasse; Aurelie Brizard; Ivan Huc; Reiko Oda. Density functional theory calculations of vibrational absorption and circular dichroism spectra of dimethyl-L-tartrate. J. Phys. Chem. A. 2004, 108,(18), 4080-4086.

Has been used in Sharpless epoxidation of allylic alcohols; see tert-Butyl­ hydroperoxide, A13926.

Cyclic ketals formed with dimethyl tartrate as the diol component undergo highly selective bromination: Angew. Chem. Int. Ed., 25, 259 (1986).

Other References

Beilstein
1726256
Harmonized Tariff Code
2918.13
TSCA
Yes

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