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349003

Sigma-Aldrich

(1R)-(−)-(10-Camphorsulfonyl)oxaziridine

Synonym(s):

(1R)-(−)-(Camphorylsulfonyl)oxaziridine, (1R)-(−)-2,N-Epoxy-exo-10,2-bornanesultam

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About This Item

Empirical Formula (Hill Notation):
C10H15NO3S
CAS Number:
104372-31-8
Molecular Weight:
229.30
Beilstein/REAXYS Number:
6274369
MDL number:
MFCD00075428
UNSPSC Code:
12352005
PubChem Substance ID:
24861490
NACRES:
NA.22

form

powder

optical activity

[α]20/D −44°, c = 2.2 in chloroform

storage temp.

2-8°C

SMILES string

[H][C@@]12CC[C@@]3(CS(=O)(=O)N4OC34C1)C2(C)C

InChI

1S/C10H15NO3S/c1-8(2)7-3-4-9(8)6-15(12,13)11-10(9,5-7)14-11/h7H,3-6H2,1-2H3/t7-,9-,10?,11?/m1/s1

InChI key

GBBJBUGPGFNISJ-JRNSMZEGSA-N

Application

(1R)-(-)-(10-Camphorsulfonyl)oxaziridine may be used as an oxidant to prepare (S)-(-)-vasicinone via asymmetric oxidation of deoxyvasicinone.
Reactant involved in:
  • Asymmetric synthesis of proton pump inhibitors
  • Asymmetric synthesis of polyhydroxylated pyrrolidines
  • Diastereoselective hydroxylation of chlorophylls a and b enolate anions

Used in impregnated silica nanoparticles for removal of sulfur mustard from wastewater

Used to modify blebbistatin for investigations of myosin inhibitor design

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Certificates of Analysis (COA)

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Synthesis of Optically Active Vasicinone Based on Intramolecular Aza-Wittig Reaction and Asymmetric Oxidation1.
Eguchi S, et al.
The Journal of Organic Chemistry, 61(21), 7316-7319 (1996)

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