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447447

Sigma-Aldrich

(4S,5R)-(−)-cis-4,5-Diphenyl-2-oxazolidinone

98%

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About This Item

Empirical Formula (Hill Notation):
C15H13NO2
CAS Number:
23204-70-8
Molecular Weight:
239.27
MDL number:
MFCD00799526
UNSPSC Code:
12352005
PubChem Substance ID:
24868340
NACRES:
NA.22

assay

98%

optical activity

[α]23/D −57±4°, c = 2 in chloroform (or methanol)

mp

227-232 °C (lit.)

functional group

phenyl

SMILES string

O=C1N[C@H]([C@H](O1)c2ccccc2)c3ccccc3

InChI

1S/C15H13NO2/c17-15-16-13(11-7-3-1-4-8-11)14(18-15)12-9-5-2-6-10-12/h1-10,13-14H,(H,16,17)/t13-,14+/m0/s1

InChI key

LTENIVFVXMCOQI-UONOGXRCSA-N

Application

Versatile chiral auxiliary used in a variety of highly diastereoselective reactions such as Michael additions,[1] Diels-Alder reactions,[2] cyclopropanations,[3] and allylations.[4]

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
MKCG8879
MKBF7488V
MKBD2447
07622CH
16426KD

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Davies, I.W. et al.
Tetrahedron Letters, 36, 7619-7619 (1995)
Arun K. Ghosh et al.
The Journal of organic chemistry, 61(18), 6175-6182 (1996-09-06)
Sinefungin (1) a nucleoside antibiotic isolated from Streptomyces has been synthesized from D-ribose. Both the C-6 and C-9 stereogenic centers were constructed by efficient asymmetric syntheses. The C-6 amine stereochemistry was set by a highly diastereoselective allylation (>99% de) of
Akiba, T. et al.
Tetrahedron, 50, 3905-3905 (1994)
Davies, S.G. Sanganee, H.J.
Tetrahedron Asymmetry, 6, 671-671 (1995)

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