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294640

Sigma-Aldrich

(S)-4-Benzyl-2-oxazolidinone

99%

Synonym(s):

(4S)-(-)-4-(Phenylmethyl)-1,3-oxazolidin-2-one, (4S)-4-(Phenylmethyl)-2-oxazolidinone, (4S)-4-benzyl-1,3-oxazolidin-2-one, (S)-(-)-4-benzyl-2-oxazolidinone, (S)-4-benzyloxazolidin-2-one

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About This Item

Empirical Formula (Hill Notation):
C10H11NO2
CAS Number:
90719-32-7
Molecular Weight:
177.20
Beilstein:
3649667
MDL number:
MFCD00064496
UNSPSC Code:
12352005
PubChem Substance ID:
24857725
NACRES:
NA.22

Assay

99%

form

solid

optical activity

[α]20/D −63°, c = 1 in chloroform

optical purity

ee: 99% (HPLC)

mp

86-88 °C (lit.)

SMILES string

O=C1N[C@H](CO1)Cc2ccccc2

InChI

1S/C10H11NO2/c12-10-11-9(7-13-10)6-8-4-2-1-3-5-8/h1-5,9H,6-7H2,(H,11,12)/t9-/m0/s1

InChI key

OJOFMLDBXPDXLQ-VIFPVBQESA-N

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Application

Chiral auxiliary for asymmetric alkylation.
Chiral auxiliary used recently in a synthesis of (S)-equol. Preparation and functionalization of chiral, stabilized ylides.
Used for asymmetric synthesis of (3R)- and (3S)-piperazic acid.

Pictograms

Health hazardExclamation mark
GHS08,GHS07

Signal Word

Warning

Hazard Statements

H302,H373

Hazard Classifications

Acute Tox. 4 Oral - STOT RE 2

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Jennifer M Heemstra et al.
Organic letters, 8(24), 5441-5443 (2006-11-17)
The first enantioselective total synthesis of (S)-equol is reported. The described route relies on an Evans alkylation to form the stereocenter and an intramolecular Buchwald etherification to generate the chroman ring. Key features of this method include its brevity, its
Tetrahedron Letters, 33, 7613-7613 (1992)
Arun K Ghosh et al.
Journal of the American Chemical Society, 126(12), 3704-3705 (2004-03-25)
An enantioselective first total syntheis of amphidinolide W (2) and a revision of its C6 absolute stereochemistry (1) are described. Amphidinolide W (1), a 12-membered macrolide isolated from Amphidinium sp., has shown potent antitumor properties against a variety of NCI
Robert K Boeckman et al.
The Journal of organic chemistry, 71(23), 8969-8972 (2006-11-04)
Camphor-derived lactams and other related chiral controllers have been found to react with the Bestmann ylide (triphenylphosphoranylideneketene) upon heating in toluene. The resulting parent ylides provide convenient access to a structurally diverse set of chiral stabilized ylides via functionalization. The
Anne N Shemon et al.
PloS one, 4(6), e6028-e6028 (2009-06-25)
Raf Kinase Inhibitory Protein (RKIP, also PEBP1), a member of the Phosphatidylethanolamine Binding Protein family, negatively regulates growth factor signaling by the Raf/MAP kinase pathway. Since an organic compound, locostatin, was reported to bind RKIP and inhibit cell migration by

Chromatograms

application for HPLC

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