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374318

Dimethyl (S)-(−)-malate

Name: Dimethyl (<I>S</I>)-(−)-malate
Brand: ALDRICH

98%

Synonym(s):

Dimethyl (S)-2-hydroxysuccinate, Dimethyl L-malate

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About This Item

Linear Formula:

CH₃O₂CCH₂CH(OH)CO₂CH₃

CAS Number:

617-55-0

Molecular Weight:

162.14

UNSPSC Code:

12352108

NACRES:

NA.22

PubChem Substance ID:

24863298

EC Number:

432-310-0

Beilstein/REAXYS Number:

1724363

MDL number:

MFCD00066215

Assay:

98%

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Properties

Quality Level

200

assay

98%

optical activity

[α]20/D −6.5°, neat

refractive index

n20/D 1.435 (lit.)

density

1.223 g/mL at 25 °C (lit.)

functional group

ester, hydroxyl

storage temp.

2-8°C

SMILES string

COC(=O)C[C@H](O)C(=O)OC

InChI

1S/C6H10O5/c1-10-5(8)3-4(7)6(9)11-2/h4,7H,3H2,1-2H3/t4-/m0/s1

InChI key

YSEKNCXYRGKTBJ-BYPYZUCNSA-N

Description

Application

Dimethyl (S)-(-)-malate may be used as a starting material to synthesize (-)-tulipalin B. The selective reduction of its ester group to alcohol can be accomplished using borane-dimethyl sulfide complex (BMS) in the presence of sodium tetrahydroborate.

This chiral synthon has been used to prepare cytochrome P450 metabolites of arachidonic acid, and cyclic sulfolanes with HIV-1 protease inhibition potential.