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456497

Sigma-Aldrich

Benzyl (R)-(−)-mandelate

99%

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About This Item

Linear Formula:
C6H5CH(OH)CO2CH2C6H5
CAS Number:
97415-09-3
Molecular Weight:
242.27
MDL number:
MFCD00674031
UNSPSC Code:
12352108
PubChem Substance ID:
24869188
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.
It can also be used to prepare HMG-CoA reductase inhibitors.

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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Certificates of Analysis (COA)

Lot/Batch Number
16129LI
05027HQ
13519HB
12410BB
10023CC

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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)
Konoike, T. Araki, Y.
The Journal of Organic Chemistry, 59, 7849-7849 (1994)
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)
Stereoselective Pseudomonas cepacia lipase mediated synthesis of α-hydroxyamides
Adamczyk M, et al.
Tetrahedron Asymmetry, 8(15), 2509-2512 (1997)
AlkylFluor: Deoxyfluorination of Alcohols.
Goldberg NW, et al.
Organic Letters, 18(23), 6102-6104 (2016)

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