447447
(4S,5R)-(−)-cis-4,5-Diphenyl-2-oxazolidinone
98%
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About This Item
Empirical Formula (Hill Notation):
C15H13NO2
CAS Number:
Molecular Weight:
239.27
MDL number:
UNSPSC Code:
12352005
PubChem Substance ID:
NACRES:
NA.22
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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, Diels-Alder reactions, cyclopropanations, and allylations.
Signal Word
Warning
Hazard Statements
Precautionary Statements
Hazard Classifications
Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
Target Organs
Respiratory system
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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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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