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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/REAXYS Number:
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

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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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