56655
(−)-Methyl (R)-3-hydroxyvalerate
≥98.0% (sum of enantiomers, GC)
Synonym(s):
(−)-Methyl (R)-3-hydroxypentanoate
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About This Item
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Quality Level
Assay
≥98.0% (sum of enantiomers, GC)
optical activity
[α]20/D −37±3°, c = 1% in chloroform
refractive index
n20/D 1.427
bp
68-70 °C/5 mmHg (lit.)
density
1.029 g/mL at 20 °C (lit.)
functional group
ester
hydroxyl
SMILES string
CC[C@@H](O)CC(=O)OC
InChI
1S/C6H12O3/c1-3-5(7)4-6(8)9-2/h5,7H,3-4H2,1-2H3/t5-/m1/s1
InChI key
XHFXKKFVUDJSPJ-RXMQYKEDSA-N
Application
- Preparation of single-enantiomer 2-methyl-4-heptanol, a pheromone of Metamasius hemipterus, using (S)-2-methoxy-2-(1-naphthyl)propionic acid.: This research outlines the synthesis of a single-enantiomer pheromone compound using (S)-2-methoxy-2-(1-naphthyl)propionic acid. The process highlights the importance of enantiopure intermediates like (−)-Methyl (R)-3-hydroxyvalerate in the synthesis of biologically active compounds (Ichikawa and Ono, 2006).
Other Notes
Chiral building block for EPC syntheses; selective anti-alkylation of its dianion; OH protection and reduction of ester group to aldehyde or alcohol functions; stereoselective preparation of a dioxanone with pivalaldehyde
Storage Class Code
10 - Combustible liquids
WGK
WGK 3
Flash Point(F)
168.8 °F - closed cup
Flash Point(C)
76 °C - closed cup
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
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Tetrahedron Letters, 27, 2091-2091 (1986)
Helvetica Chimica Acta, 62, 2825-2825 (1979)
Tetrahedron, 41, 919-919 (1985)
Helvetica Chimica Acta, 70, 1104-1104 (1987)
Liebigs Ann. Chem., 159-159 (1990)
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