| Identification | Back Directory | [Name]
D-(-)-MANDELIC ACID BENZYL ESTER | [CAS]
97415-09-3 | [Synonyms]
DOMIT-002
(R)-BENZYL MANDELATE
BENZYL D-(-)-MANDELATE
BENZYL (R)-(-)-MANDELATE
BenzylD-(-)-Mandelate>
Benzyl (R)-(-)-mandelate 99%
D-(-)-MANDELIC ACID BENZYL ESTER
-Benzyl 2-hydroxy-2-phenylacetate
(R)-Benzyl 2-hydroxy-2-phenylacetate
benzyl (2R)-2-hydroxy-2-phenylacetate
Benzyl D-(-)-Mandelate
Benzyl-(R)-Mandelate / Benzyl-(D)-Mandelate
ALPHA-HYDROXY-BENZENEACETIC ACID, PHENYLMETHYL ESTER
D-(-)-MANDELIC ACID BENZYL ESTER ISO 9001：2015 REACH
Benzeneacetic acid, α-hydroxy-, phenylmethyl ester, (αR)- | [EINECS(EC#)]
1312995-182-4 | [Molecular Formula]
C15H14O3 | [MDL Number]
MFCD00674031 | [MOL File]
97415-09-3.mol | [Molecular Weight]
242.27 |
| Chemical Properties | Back Directory | [Melting point ]
104-107 °C(lit.)
| [Boiling point ]
387℃ | [density ]
1.204 | [refractive index ]
-34 ° (C=1, CH3CN) | [Fp ]
163℃ | [storage temp. ]
Sealed in dry,Room Temperature | [solubility ]
DMF: 30 mg/ml; DMF:PBS (pH 7.2) (1:2): 0.3 mg/ml; DMSO: 25 mg/ml; Ethanol: 20 mg/ml | [form ]
powder to crystal | [pka]
12.15±0.20(Predicted) | [color ]
White to Almost white | [Optical Rotation]
[α]25/D 55°, c = 1 in chloroform | [CAS DataBase Reference]
97415-09-3 |
| Hazard Information | Back Directory | [Description]
(R)-benzyl Mandelate is a synthetic intermediate useful for pharmaceutical synthesis. | [Uses]
Benzyl (R)-(-)-mandelate can be employed as reactant to synthesize:
- (S)-α-Hydroxy-N-(2-phenylethyl)benzenepropanamide (α-hydroxyamides) by enzyme catalyzed amidation reaction.
- Optically pure (R)- monomethyl esters of 3-[(tert-butyldimethylsilyl)oxy]pentanedioic acid, which is employed in the preparation of HMG-CoA reductase inhibitors.
- O-Ibuprofenylmandelic acid via acylation reaction with optically active ibuprofen and subsequent hydrogenation.
- Benzyl (R)-2-fluoro-2-phenylacetate via deoxyfluorination of alcohols using AlkylFluor.
It can also be used to prepare HMG-CoA reductase inhibitors. | [Uses]
D-(-)-Mandelic Acid Benzyl Ester is a useful reagent for the preparation of a pharmaceutical composition for treating atopic dermatitis. | [Synthesis]
(1) Synthesis of benzyl (R)-2-hydroxy-2-phenylacetate (D-2): 85.1 g (559 mmol) of D-mandelic acid, 65 mL (628 mmol) of benzyl alcohol, and 1.01 g (5.35 mmol) of p-toluenesulfonic acid were dissolved in 700 mL of benzene, and the reaction was carried out at reflux for 6.5 hours. Upon completion of the reaction, the reaction mixture was washed with water and subsequently concentrated. The residue was recrystallized by ether to give 123.5 g (R)-benzyl 2-hydroxy-2-phenylacetate (D-2) in 91% yield. The melting point was 103.5°C-105°C. Elemental analysis (C15H14O3) Calculated values (%): C, 74.36; H, 5.82; Measured values (%): C, 74.53; H, 5.90. 1H-NMR (CDCl3-TMS) δ (ppm): 3.44 (d, J = 5.6 Hz, 1H), 5.14 (ABq, isolated, J = 12.3 Hz, 1H). J = 12.3 Hz, 1H), 5.22 (d, J = 5.6 Hz, 1H), 5.24 (ABq, Part B, J = 12.3 Hz, 1H), 7.15-7.50 (m, 10H). [α]D = -55.7 ± 1.0 (CHCl3, c = 1.003%, 24°C). | [References]
[1] Patent: US5047574, 1991, A |
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