456497
Benzyl (R)-(−)-mandelate
99%
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About This Item
Linear Formula:
C6H5CH(OH)CO2CH2C6H5
CAS Number:
Molecular Weight:
242.27
MDL number:
UNSPSC Code:
12352108
PubChem Substance ID:
NACRES:
NA.22
Assay
99%
form
solid
optical activity
[α]25/D −55°, c = 1 in chloroform
mp
104-107 °C (lit.)
SMILES string
O[C@@H](C(=O)OCc1ccccc1)c2ccccc2
InChI
1S/C15H14O3/c16-14(13-9-5-2-6-10-13)15(17)18-11-12-7-3-1-4-8-12/h1-10,14,16H,11H2/t14-/m1/s1
InChI key
JFKWZVQEMSKSBU-CQSZACIVSA-N
Application
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.
Storage Class Code
11 - Combustible Solids
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
Regulatory Information
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Practical synthesis of chiral synthons for the preparation of HMG-CoA reductase inhibitors
Konoike T and Araki Y
The Journal of Organic Chemistry, 59(25), 7849-7854 (1994)
Konoike, T. Araki, Y.
The Journal of Organic Chemistry, 59, 7849-7849 (1994)
Stereoselective Pseudomonas cepacia lipase mediated synthesis of α-hydroxyamides
Adamczyk M, et al.
Tetrahedron Asymmetry, 8(15), 2509-2512 (1997)
Preparation of optically active (acyloxy) alkyl esters from optically active O-acyl-α-hydroxy acids
Guzzo Peter R, et al.
Tetrahedron Letters, 43(32), 5685-5689 (2002)
AlkylFluor: Deoxyfluorination of Alcohols.
Goldberg NW, et al.
Organic Letters, 18(23), 6102-6104 (2016)
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