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Key Documents

COO/COA

463965

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

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

97%

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About This Item

Empirical Formula (Hill Notation):

C₁₀H₉NO₂

CAS Number:

135969-65-2

Molecular Weight:

175.18

MDL number:

MFCD00674088

UNSPSC Code:

12352005

PubChem Substance ID:

24870124

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

GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Precautionary Statements

P261 - P305 + P351 + P338

Hazard Classifications

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

Storage Class Code

13 - Non 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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Certificates of Analysis (COA)

Lot/Batch Number

20231KO

08203LQ

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Davies, I.W. et al.

Tetrahedron Letters, 36, 7619-7619 (1995)

Akiba, T. et al.

Tetrahedron, 50, 3905-3905 (1994)

Total Synthesis of (+)-Sinefungin.

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)

Chromatograms

HPLC Analysis of Cis-(+/-)-3,3a,8,8a-Tetrahydro-2H-indeno[1,2-d]oxazol-2-one Enantiomers on Astec^® (R,R) P-CAP^™-DP

application for HPLC

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