| Identification | More | [Name]
Dimethyl 3-hydroxyglutarate | [CAS]
7250-55-7 | [Synonyms]
3-hydroxyglutaric acid dimethyl ester
DIMETHYL 3-HYDROXYGLUTARATE
Dimethyl 3-hydroxypentanedioate
Pentanedioic acid, 3-hydroxy-, dimethyl ester
NISTC7250557 | [Molecular Formula]
C7H12O5 | [MDL Number]
MFCD00042841 | [Molecular Weight]
176.17 | [MOL File]
7250-55-7.mol |
| Safety Data | Back Directory | [Safety Statements ]
S23:Do not breathe gas/fumes/vapor/spray (appropriate wording to be specified by the manufacturer) .
S24/25:Avoid contact with skin and eyes . | [WGK Germany ]
3
| [HS Code ]
29181990 |
| Hazard Information | Back Directory | [Chemical Properties]
Off-White to Pale Yellow Oil | [Uses]
Dimethyl 3-hydroxyglutarate was used in the synthesis of two chiral fragments representing C1-11 and C12-25 of the polyene macrolide pimaricin. | [Uses]
Glutaric Acid derivative | [General Description]
Enantioselective hydrolysis and ammonolysis of dimethyl-3-hydroxyglutarate has been studied using immobilized lipase B isolated from Candida antarctica. | [Synthesis]
To a stirred solution of dimethyl 3-oxoglutarate (17.7 mL, 120.6 mmol) in methanol (315 mL) at 0 °C was added sodium borohydride (3.9 g, 102.5 mmol) in batches. After the reaction mixture was brought to room temperature, the reaction was continued with stirring for 24 hours. Upon completion of the reaction, the pH of the reaction mixture was adjusted to 5-6 by adding solid citric acid to quench the reaction. Subsequently, silica gel (about 1 g) was added to the reaction mixture and the solvent was removed by rotary evaporation. The residue was purified by silica gel column chromatography (eluent: ethyl acetate/hexane, 1:1) to afford dimethyl 3-hydroxyglutarate (19.98 g, 94% yield) as a colorless oil. | [References]
[1] Journal of the Brazilian Chemical Society, 2011, vol. 22, # 1, p. 172 - 175
[2] Bioorganic and Medicinal Chemistry Letters, 2015, vol. 25, # 17, p. 3650 - 3653
[3] Journal of Organic Chemistry, 1988, vol. 53, # 7, p. 1567 - 1569
[4] RSC Advances, 2016, vol. 6, # 27, p. 22737 - 22748
[5] Journal of the American Chemical Society, 2009, vol. 131, # 49, p. 17980 - 17985 |
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