| Identification | More | [Name]
METHYL (S)-(+)-3-HYDROXY-2-METHYLPROPIONATE | [CAS]
80657-57-4 | [Synonyms]
L(+)-BETA-HYDROXYISOBUTYRIC ACID METHYL ESTER
L-(S)-(+)-3-HYDROXYISOBUTYRIC ACID METHYL ESTER
(+)-METHYL L-BETA-HYDROXYISOBUTYRATE
METHYL L-(S)-3-HYDROXYISOBUTYRATE
METHYL (S)-(+)-3-HYDROXY-2-METHYLPROPIONATE
METHYL (S)-3-HYDROXY-2-METHYLPROPIONATE
METHYL (S)-(+)-3-HYDROXYISOBUTYRATE
(S)-(+)-3-HYDROXY-2-METHYLPROPIONIC ACID METHYL ESTER
(S)-3-HYDROXY-2-METHYLPROPIONIC ACID METHYL ESTER
(S)-(+)-3-HYDROXYISOBUTYRIC ACID METHYL ESTER
(S)-(+)-METHYL 3-HYDROXY-2-METHYLPROPIONATE
(S)-(+)-METHYL B-HYDROXYISOBUTYRATE
Propanoicacid,3-hydroxy-2-methyl-methylester
methyl (S)-(+)-3-hydroxy-2-methyl-*propionate 99%
Methyl-L-(S)-beta-hydroxyisobutyrate
METHYL (S)-(+)-3-HYDROXY-2-METHYL-PROPIO NATE, 99% (99% EE/GLC)
Propanoic acid, 3-hydroxy-2-methyl-, methyl ester, (2S)-
(+)-methyl l-β-hydroxyisobutyrate
3-hydroxyisobutyric acid methyl ester
methyl beta-hydroxyisobutyrate | [EINECS(EC#)]
203-310-6 | [Molecular Formula]
C5H10O3 | [MDL Number]
MFCD00064520 | [Molecular Weight]
118.13 | [MOL File]
80657-57-4.mol |
| Chemical Properties | Back Directory | [Boiling point ]
74 °C/10 mmHg (lit.) | [density ]
1.071 g/mL at 25 °C(lit.)
| [refractive index ]
n20/D 1.425
| [Fp ]
178 °F
| [storage temp. ]
Sealed in dry,2-8°C | [solubility ]
Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly) | [form ]
Liquid | [pka]
14.40±0.10(Predicted) | [color ]
Colorless | [Specific Gravity]
1.07 | [Optical Rotation]
[α]19/D +26°, c = 4 in methanol | [Water Solubility ]
Insoluble in water. Soluble in methanol. | [BRN ]
1720830 | [InChI]
InChI=1S/C5H10O3/c1-4(3-6)5(7)8-2/h4,6H,3H2,1-2H3/t4-/m0/s1 | [InChIKey]
ATCCIZURPPEVIZ-BYPYZUCNSA-N | [SMILES]
C(OC)(=O)[C@@H](C)CO | [CAS DataBase Reference]
80657-57-4(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xn | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin .
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
S36:Wear suitable protective clothing . | [RIDADR ]
1993 | [WGK Germany ]
3
| [HazardClass ]
3.2 | [PackingGroup ]
III | [HS Code ]
29181990 |
| Hazard Information | Back Directory | [Chemical Properties]
Clear colorless liquid | [Uses]
Methyl (S)-(+)-3-hydroxy-2-methylpropionate is used as a starting material for the synthesis of dictyostatin, discodermolide and spongidepsin. | [Synthesis]
General procedure for the synthesis of methyl (S)-(+)-3-hydroxy-2-methylpropanoate and (-)-methyl-D-BATA-hydroxyisobutyrate from methyl 2-(hydroxymethyl)acrylate: K.3. Typical method for asymmetric catalytic hydrogenation is as follows: [Rh(COD)L*]BF4 (0.005 mmol, 1 mol%) and substrate (0.5 mmol) were were dissolved in a dry solvent (7.5 mL) and the solution was transferred to a stainless steel autoclave. After sealing the autoclave, it was purged with hydrogen and then pressurized with hydrogen. After stirring the reaction mixture for 16 h at room temperature, the hydrogen was slowly released to atmospheric pressure and the reaction solution was transferred to a round bottom flask. The solvent was removed using a rotary evaporator to obtain the crude product. The crude product was purified by silica gel column chromatography to give the hydrogenated product. The enantiomeric excess value of the product was determined by chiral column HPLC. The results of asymmetric catalytic hydrogenation using rhodium complexes of ligands (1-48) or (1-49) are presented in Tables 9 and 10, respectively. Table 9 demonstrates the results of asymmetric catalytic hydrogenation of rhodium complexes of ligand (1-48) under different conditions including substrate, solvent, pressure, conversion and enantiomeric excess values. Table 10, on the other hand, shows the results of asymmetric catalytic hydrogenation of rhodium complexes of ligand (I'-49c) under the same conditions. | [References]
[1] Advanced Synthesis and Catalysis, 2003, vol. 345, # 1-2, p. 185 - 189
[2] Advanced Synthesis and Catalysis, 2007, vol. 349, # 10, p. 1592 - 1596
[3] Advanced Synthesis and Catalysis, 2007, vol. 349, # 10, p. 1592 - 1596
[4] Tetrahedron Asymmetry, 2009, vol. 20, # 2, p. 210 - 213
[5] Advanced Synthesis and Catalysis, 2008, vol. 350, # 10, p. 1610 - 1614 |
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