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Sigma-Aldrich

(S)-4-Benzyl-2-oxazolidinone

99%

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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
Empirical Formula (Hill Notation):
C10H11NO2
CAS Number:
Molecular Weight:
177.20
Beilstein:
3649667
MDL number:
PubChem Substance ID:
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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This Item
228001SML1629PHR3701
Ezetimibe ≥98% (HPLC)

Sigma-Aldrich

SML1629

Ezetimibe

form

solid

form

liquid

form

powder

form

-

optical activity

[α]20/D −63°, c = 1 in chloroform

optical activity

-

optical activity

-

optical activity

-

mp

86-88 °C (lit.)

mp

15 °C (lit.)

mp

-

mp

107-111 °C

Quality Level

200

Quality Level

200

Quality Level

200

Quality Level

300

optical purity

ee: 99% (HPLC)

optical purity

-

optical purity

-

optical purity

-

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

Exclamation markHealth hazard

Signal Word

Warning

Hazard Statements

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

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Customers Also Viewed

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

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