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270148

Sigma-Aldrich

Methyl (R)-(−)-3-hydroxy-2-methylpropionate

99%

Synonym(s):

(−)-Methyl D-β-hydroxyisobutyrate, (R)-(−)-3-Hydroxy-2-methylpropionic acid methyl ester

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About This Item

Linear Formula:
HOCH2CH(CH3)CO2CH3
CAS Number:
72657-23-9
Molecular Weight:
118.13
Beilstein/REAXYS Number:
3587507
MDL number:
MFCD00063450
UNSPSC Code:
12352108
PubChem Substance ID:
24856357
NACRES:
NA.22

Quality Level

200

assay

99%

form

liquid

optical activity

[α]19/D −26°, c = 4 in methanol

optical purity

ee: 99% (GLC)

refractive index

n20/D 1.425 (lit.)

bp

76-77 °C/12 mmHg (lit.)

density

1.066 g/mL at 25 °C (lit.)

SMILES string

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

InChI

1S/C5H10O3/c1-4(3-6)5(7)8-2/h4,6H,3H2,1-2H3/t4-/m1/s1

InChI key

ATCCIZURPPEVIZ-SCSAIBSYSA-N

Related Categories

Application

Methyl (R)-(-)-3-hydroxy-2-methylpropionate may be used in the preparation of (S)-(4-benzyloxy-3-methylbut-1-ynyl)triethylsilane. It may also be used as a starting material in the total synthesis of (-)-discodermolide, (-)-stemoamide and (-)-stemospironine.
The (R)- and (S)-isomers are bifunctional building blocks for the synthesis of a wide variety of optically active molecules.

wgk_germany

WGK 3

flash_point_f

176.0 °F

flash_point_c

80 °C

ppe

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter

Certificates of Analysis (COA)

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Tetrahedron Letters, 34, 5939-5939 (1993)
Distinct binding and cellular properties of synthetic (+)-and (-)-discodermolides.
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Chemistry & Biology, 1(1), 67-71 (1994)
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