| Identification | Back Directory | [Name]
(R)-Methyl 2,3-dihydroxypropanoate | [CAS]
18289-89-9 | [Synonyms]
Methyl D-(-)-glycerate
Methyl (R)-2,3-Dihydroxypropionate
(R) Methyl-2,3-dihydroxypropionate
methyl (R)-2,3-dihydroxypropanoate
(R)-Methyl 2,3-dihydroxypropanoate
methyl (2R)-2,3-dihydroxypropanoate
Propanoic acid, 2,3-dihydroxy-, methyl ester, (2R)- | [Molecular Formula]
C4H8O4 | [MDL Number]
MFCD06204263 | [MOL File]
18289-89-9.mol | [Molecular Weight]
120.1 |
| Chemical Properties | Back Directory | [Boiling point ]
140 °C(Press: 15 Torr) | [density ]
1.2795 g/cm3 | [storage temp. ]
2-8°C | [pka]
12.26±0.20(Predicted) | [Appearance]
Light yellow to yellow Liquid | [Optical Rotation]
12.5°(C=0.01g/ml CHCL3) | [InChI]
InChI=1S/C4H8O4/c1-8-4(7)3(6)2-5/h3,5-6H,2H2,1H3/t3-/m1/s1 | [InChIKey]
COFCNNXZXGCREM-GSVOUGTGSA-N | [SMILES]
C(OC)(=O)[C@H](O)CO |
| Hazard Information | Back Directory | [Synthesis]
General procedure for the synthesis of methyl (R)-2,3-dihydroxypropionate from methyl (R)-(+)-2,2-dimethyl-1,3-dioxolane-4-carboxylate:
1. dissolve methyl (R)-(+)-2,2-dimethyl-1,3-dioxolane-4-carboxylate (1 g, 6.24 mmol) in a mixed solvent of acetic acid (14 ml) and water (6 ml).
2. The reaction mixture was stirred at room temperature for 18 hours.
3. After completion of the reaction, the solvent was removed by evaporation under reduced pressure.
4. The resulting residue was distilled three times azeotropically with toluene to completely remove water and residual acetic acid.
5. Methyl (R)-2,3-dihydroxypropionate (610.6 mg, 81% yield) was finally obtained.
Product characterization data: 1H NMR (CDCl3, 400MHz) δ 4.29 (dd, 1H, J = 3.8, 3.3Hz), 3.91 (dd, 1H, J = 11.7, 3.3Hz), 3.85 (dd, 1H, J = 11.7, 3.8Hz), 3.84 (s, 3H). | [References]
[1] Journal of Medicinal Chemistry, 1992, vol. 35, # 17, p. 3223 - 3230
[2] Acta Chemica Scandinavica, 1998, vol. 52, # 6, p. 819 - 823
[3] Patent: US2006/270634, 2006, A1. Location in patent: Page/Page column 2; sheet 4
[4] Angewandte Chemie - International Edition, 2015, vol. 54, # 34, p. 9898 - 9902
[5] Angew. Chem., 2015, vol. 127, # 34, p. 10036 - 10040,5 |
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