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    (-)-Sparteine
    Information
    CAS No. 24915-04-6 Price $218 / 10mg
    Catalog No.CFN90180Purity>=98%
    Molecular Weight234.38Type of CompoundAlkaloids
    FormulaC15H26N2Physical DescriptionPowder
    Download Manual    COA    MSDSSimilar structuralComparison (Web)
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    (-)-Sparteine Description
    Source: The herbs of Parochetus communis
    Biological Activity or Inhibitors: 1. Sparteine is a class 1a antiarrhythmic agent, a sodium channel blocker.
    2. The deficient debrisoquine hydroxylation of Sparteine is due to the absence of P-450IID1 protein in the livers of poor metabolizers.
    Solvent: Chloroform, Dichloromethane, Ethyl Acetate, DMSO, Acetone, etc.
    Storage: Providing storage is as stated on the product vial and the vial is kept tightly sealed, the product can be stored for up to 24 months(2-8C).

    Wherever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20C. Generally, these will be useable for up to two weeks. Before use, and prior to opening the vial we recommend that you allow your product to equilibrate to room temperature for at least 1 hour.

    Need more advice on solubility, usage and handling? Please email to: service@chemfaces.com

    After receiving: The packaging of the product may have turned upside down during transportation, resulting in the natural compounds adhering to the neck or cap of the vial. take the vial out of its packaging and gently shake to let the compounds fall to the bottom of the vial. for liquid products, centrifuge at 200-500 RPM to gather the liquid at the bottom of the vial. try to avoid loss or contamination during handling.
    Calculate Dilution Ratios(Only for Reference)
    1 mg 5 mg 10 mg 20 mg 25 mg
    1 mM 4.2666 mL 21.3329 mL 42.6658 mL 85.3315 mL 106.6644 mL
    5 mM 0.8533 mL 4.2666 mL 8.5332 mL 17.0663 mL 21.3329 mL
    10 mM 0.4267 mL 2.1333 mL 4.2666 mL 8.5332 mL 10.6664 mL
    50 mM 0.0853 mL 0.4267 mL 0.8533 mL 1.7066 mL 2.1333 mL
    100 mM 0.0427 mL 0.2133 mL 0.4267 mL 0.8533 mL 1.0666 mL
    * Note: If you are in the process of experiment, it's need to make the dilution ratios of the samples. The dilution data of the sheet for your reference. Normally, it's can get a better solubility within lower of Concentrations.
    (-)-Sparteine References Information
    Citation [1]

    J Am Chem Soc. 2010 Oct 6;132(39):13922-7.

    Synthesis of P-stereogenic compounds via kinetic deprotonation and dynamic thermodynamic resolution of phosphine sulfides: opposite sense of induction using (-)-sparteine.[Pubmed: 20843035]
    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 via a kinetically controlled process that was successfully predicted using a computational approach at the B3LYP/6-31+G(d) level. This initial kinetic enantioselectivity could be enhanced up to 97:3 er by trapping the lithiated intermediate with a prochiral electrophile (e.g., pivaldehyde or tBuPCl(2)). In addition, it was found that the R(P) and S(P) stereoisomers of the lithiated methylphosphine sulfide could interconvert at temperatures above 0 °C. Such interconversion is unprecedented and differs from the configurational instability of organolithiums that are stereogenic at a lithiated carbon atom. The major, thermodynamically preferred diastereomeric (-)-Sparteine-complexed lithated phosphine sulfide was investigated by X-ray crystallography and computational methods at the B3LYP/6-31+G(d) level. Through the interconversion of the R(P) and S(P) stereoisomers of the lithiated methylphosphine sulfide, a novel dynamic thermodynamic resolution of a racemic lithiated phosphine sulfide has been developed. Thus, the phosphine sulfide was lithiated with nBuLi, and then (-)-Sparteine was added. After equilibration at 0 °C for 3 h, electrophilic trapping generated an adduct in 81:19 er with the configuration opposite to that obtained under kinetic control. Thus, the methodology provides access to P-stereogenic compounds with the opposite sense of induction using (-)-Sparteine as the ligand simply by changing the reaction conditions (kinetic or thermodynamic control).
    Citation [2]

    Org Biomol Chem. 2014 Dec 14;12(46):9357-65.

    Revisiting the sparteine surrogate: development of a resolution route to the (-)-sparteine surrogate.[Pubmed: 25297971]
    The improved performance of the sparteine surrogate compared to sparteine in a range of applications has highlighted the need to develop an approach to the (-)-Sparteine surrogate, previously inaccessible in gram-quantities. A multi-gram scale, chromatography-free synthesis of the racemic sparteine surrogate and its resolution via diastereomeric salt formation with (-)-O,O'-di-p-toluoyl-l-tartaric acid is reported. Resolution on a 10.0 mmol scale gave the diastereomeric salts in 33% yield from which (-)-Sparteine surrogate of 93 : 7 er was generated. This work solves a key limitation: either enantiomer of the sparteine surrogate can now be readily accessed.
    Citation [3]

    J Org Chem. 2015 Apr 3;80(7):3368-86.

    Highly enantioselective (-)-sparteine-mediated lateral metalation-functionalization of remote silyl protected ortho-ethyl N,N-dialkyl aryl O-carbamates.[Pubmed: 25521308 ]
    We report the enantioselective, lateral deprotonation of ortho-protected or functionalized tertiary N,N-dialkyl aryl O-carbamates 5-7 (Scheme 2 ) and meta-protected carbamates 14, 15, and 20 (Schemes 5 and 7 ) by s-BuLi/(-)-Sparteine and subsequent quench with a variety of electrophiles to give products 11-13 and 16, 17, and 21 in yields up to 96% and enantiomeric ratios up to 99:1. The influence of organolithium reagents, ratio of organolithium/(-)-Sparteine pair versus N,N-dialkyl aryl O-carbamate starting materials, temperature, solvents, electrophiles, substituents located ortho or meta to the O-carbamate moiety, and O-carbamate N-substituents was investigated. The identical absolute configuration of the stereogenic center of the major enantiomers of the products, as established by single-crystal X-ray analysis for substrates (S)-11c, (S)-19, and (S)-21a, provides evidence for a consistent stereochemical course in the enantioselective deprotonation. Mechanistic investigations, including an estimate of the configurational stability of the benzyllithium species 9 (starting from 12e; Scheme 8 ) and 23 (starting from 17e; Scheme 9 ), both derived by tin-lithium exchange, and 24 (starting from 20; Scheme 9 ) are reported. The experimental results, together with semiempirical molecular orbital calculations (PM3/SMD), are consistent with a process in which enantioinduction occurs in the deprotonation step (Scheme 11 ).