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Methyl (R)-3-Hydroxy-2-Methylpropionate

Catalog Number
ACM72657239-3
Product Name
Methyl (R)-3-Hydroxy-2-Methylpropionate
Structure
Methyl (R)-3-Hydroxy-2-Methylpropionate
CAS
72657-23-9
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Synonyms
(-)-Methyl D-β-hydroxyisobutyrate, (R)-(-)-3-Hydroxy-2-methylpropionic acid methyl ester
Molecular Weight
118.13
Molecular Formula
HOCH2CH(CH3)CO2CH3
Canonical SMILES
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
Boiling Point
76-77 °C/12 mmHg (lit.)
Density
1.066 g/mL at 25 °C (lit.)
Assay
0.99
Color Form
liquid
Optical Activity
[α]19/D -26°, c = 4 in methanol
Optical Purity
ee: 99% (GLC)
Refractive Index
n20/D 1.425 (lit.)
Application
The (R)- and (S)-isomers are bifunctional building blocks for the synthesis of a wide variety of optically active molecules.
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.
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