234664

Sigma-Aldrich

(−)-Sparteine sulfate pentahydrate

99%

Synonym(s):
(−)-Sparteine sulfate salt, Lupinidine sulfate pentahydrate
Empirical Formula (Hill Notation):
C15H26N2 · H2SO4 · 5H2O
CAS Number:
Molecular Weight:
422.54
MDL number:
PubChem Substance ID:

assay

99%

optical activity

[α]25/D −12.4°, c = 1 in ethanol

mp

133-140 °C (lit.)

SMILES string

O.O.O.O.O.OS(O)(=O)=O.C1CCN2C[C@@H]3C[C@@H](CN4CCCC[C@H]34)[C@@H]2C1

InChI

1S/C15H26N2.H2O4S.5H2O/c1-3-7-16-11-13-9-12(14(16)5-1)10-17-8-4-2-6-15(13)17;1-5(2,3)4;;;;;/h12-15H,1-11H2;(H2,1,2,3,4);5*1H2/t12-,13-,14-,15+;;;;;;/m0....../s1

InChI key

WNSDDGBLIALDPB-LIELMIIZSA-N

Certificate of Analysis

Certificate of Origin

Mass spectrometry of metal complexes of bis-quinolizidine alkaloids: EI and ESI mass spectral study of Co(+2), Ni(+2), Cu(+2) and Zn(+2) 2-methylsparteine complexes.
Beata Jasiewicz et al.
Journal of mass spectrometry : JMS, 47(3), 347-351 (2012-03-21)
Jonathan J Gammon et al.
Journal of the American Chemical Society, 132(39), 13922-13927 (2010-09-17)
A systematic study of the asymmetric deprotonation of a dimethyl-substituted phosphine sulfide using organolithium bases in the presence of (-)-sparteine has been carried out. Use of nBuLi and (-)-sparteine in Et(2)O at -78 °C gave trapped adducts in ∼88:12 er...
Andrew R Germain et al.
The Journal of organic chemistry, 76(8), 2577-2584 (2011-03-16)
Enantioselective syntheses of the azaphilone natural products (+)-sclerotiorin and (+)-8-O-methylsclerotiorinamine that possess the natural R-configuration at the quaternary center are reported. The syntheses were accomplished using copper-mediated asymmetric dearomatization employing bis-μ-oxo copper complexes prepared from readily available (+)-sparteine surrogates. Of...
Nattawan Decharin et al.
Journal of the American Chemical Society, 133(34), 13268-13271 (2011-07-28)
(Sp)PdCl(2) [Sp = (-)-sparteine] catalyzes a number of different aerobic oxidation reactions, and reaction of O(2) with a Pd(II)-hydride intermediate, (Sp)Pd(H)Cl (1), is a key step in the proposed catalytic mechanism. Previous computational studies suggest that O(2) inserts into the...
Kyoung Hee Kang et al.
The Journal of organic chemistry, 77(1), 808-812 (2011-12-14)
A novel method for asymmetric synthesis of trans-2,3-disubstituted indolines has been developed. The strategy involves the (-)-sparteine-mediated electrophilic substitution of 2-benzyl N-pivaloylaniline with aromatic or α,β-unsaturated aldehydes and subsequent intramolecular nucleophilic substitution. The simple protocol for two-step process can produce...

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