56655

(−)-Methyl (R)-3-hydroxyvalerate

≥98.0% (sum of enantiomers, GC)

• Synonym(s): (−)-Methyl (R)-3-hydroxypentanoate
• Empirical Formula (Hill Notation): C₆H₁₂O₃
• CAS Number: 60793-22-8
• Molecular Weight: 132.16
• Beilstein: 4655380
• MDL number: MFCD00077796
• UNSPSC Code: 12352108
• PubChem Substance ID: 57651591
• NACRES: NA.22

Properties

• 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.)
• 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

Description

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

Safety Information

• 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