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Sigma-Aldrich

(R)-4-Benzyl-2-oxazolidinone

99%

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About This Item

Empirical Formula (Hill Notation):
C10H11NO2
CAS Number:
102029-44-7
Molecular Weight:
177.20
Beilstein:
4782551
MDL number:
MFCD00010846
UNSPSC Code:
12352005
PubChem Substance ID:
24858151
NACRES:
NA.22

Assay

99%

form

powder

optical activity

[α]18/D +64°, c = 1 in chloroform

mp

88-90 °C

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-/m1/s1

InChI key

OJOFMLDBXPDXLQ-SECBINFHSA-N

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Application

(R)-4-Benzyl-2-oxazolidinone may be used as a starting material in the synthesis of enantiopure carbocyclic nucleosides. It may also be used as a chiral auxiliary in the enantioselective synthesis of (2R,2′S)-erythro-methylphenidate.
Used in the synthesis of HIV protease inhibitors.
Versatile chiral auxiliary for asymmetric synthesis. For a recent review, see Aldrichimica Acta.

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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An efficient asymmetric approach to carbocyclic nucleosides: asymmetric synthesis of 1592U89, a potent inhibitor of HIV reverse transcriptase.
Crimmins MT and King BW.
The Journal of Organic Chemistry, 61, 4192-4193 (1996)
Synlett, 4, 679-683 (2004)
Enantioselective synthesis of (2S, 2' R)-erythro-methylphenidate.
Prashad M, et al.
Tetrahedron Asymmetry, 10(18), 3479-3482 (1999)
Ager, D.J., et al.
Aldrichimica Acta, 30, 3-3 (1997)

Chromatograms

application for HPLC

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