388114
[2S-(2α,3β,8aβ)]-(+)-Hexahydro-3-(hydroxymethyl)-8a-methyl-2-phenyl-5H-oxazolo[3,2-a]pyridin-5-one
98%
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About This Item
Empirical Formula (Hill Notation):
C15H19NO3
CAS Number:
Molecular Weight:
261.32
UNSPSC Code:
12352000
PubChem Substance ID:
MDL number:
InChI
1S/C15H19NO3/c1-15-9-5-8-13(18)16(15)12(10-17)14(19-15)11-6-3-2-4-7-11/h2-4,6-7,12,14,17H,5,8-10H2,1H3/t12-,14-,15+/m1/s1
SMILES string
C[C@]12CCCC(=O)N1[C@H](CO)[C@H](O2)c3ccccc3
InChI key
HMPLCFQDHIGQMF-YUELXQCFSA-N
assay
98%
optical activity
[α]23/D +14°, c = 1 in ethanol
mp
96-100 °C (lit.)
Application
Chiral bicyclic lactams such as this are useful templates for asymmetric synthesis. High levels of asymmetric induction have been obtained in cycloadditions, alkylations, conjugate additions, annulations, and dihydroxylations.
signalword
Warning
hcodes
Hazard Classifications
Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
dust mask type N95 (US), Eyeshields, Gloves
Regulatory Information
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Brengel, G.P. Meyers, A.I.
The Journal of Organic Chemistry, 61, 3230-3230 (1996)
Romo, D. Meyers, A.I.
Tetrahedron, 47, 9503-9503 (1991)
Andres, C.J. et al.
Tetrahedron Letters, 60, 3189-3189 (1995)
Munchhoff, M.J. Meters, A.I.
The Journal of Organic Chemistry, 60, 7086-7086 (1995)
A Rapid and Efficient Approach to Chiral, Nonracemic Aza Sugars from Nonsugars. A Formal Synthesis of 1,4-Dideoxy-1,4-imino-D-lyxitol.
A. I. Meyers et al.
The Journal of organic chemistry, 61(8), 2586-2587 (1996-04-19)
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