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463965

Sigma-Aldrich

(3aR-cis)-(+)-3,3a,8,8a-Tetrahydro-2H-indeno[1,2-d]oxazol-2-one

97%

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About This Item

Empirical Formula (Hill Notation):
C10H9NO2
CAS Number:
Molecular Weight:
175.18
MDL number:
UNSPSC Code:
12352005
PubChem Substance ID:

assay

97%

optical activity

[α]22/D +76°, c = 0.65 in ethyl acetate

optical purity

ee: 99% (HPLC)

mp

203-209 °C (lit.)

SMILES string

O=C1N[C@H]2[C@H](Cc3ccccc23)O1

InChI

1S/C10H9NO2/c12-10-11-9-7-4-2-1-3-6(7)5-8(9)13-10/h1-4,8-9H,5H2,(H,11,12)/t8-,9+/m0/s1

InChI key

XWZLNPUWNUTPAU-DTWKUNHWSA-N

Application

Versatile chiral auxiliary used in a variety of highly diastereoselective reactions such as Michael additions, Diels-Alder reactions, cyclopropanations, and allylations.

pictograms

Exclamation mark

signalword

Warning

Hazard Classifications

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

Storage Class

13 - Non 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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Davies, I.W. et al.
Tetrahedron Letters, 36, 7619-7619 (1995)
Akiba, T. et al.
Tetrahedron, 50, 3905-3905 (1994)
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
Davies, S.G. Sanganee, H.J.
Tetrahedron Asymmetry, 6, 671-671 (1995)

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