(-)-Sparteine | CAS:24915-04-6 | Manufacturer ChemFaces

(-)-Sparteine

ChemFaces products have been cited in many studies from excellent and top scientific journals

Order & Inquiry & Tech Support

Tel: (0086)-27-84237683
Tech: service@chemfaces.com
Order: manager@chemfaces.com
Address: 176, CheCheng Eest Rd., WETDZ, Wuhan, Hubei 430056, PRC

How to Order

Orders via your E-mail:

1. Product number / Name / CAS No.
2. Delivery address
3. Ordering/billing address
4. Contact information
Order: manager@chemfaces.com

Delivery time

Delivery & Payment method

1. Usually delivery time: Next day delivery by 9:00 a.m. Order now

2. We accept: Wire transfer & Credit card & Paypal

Citing Use of our Products

More Impact Factor than five Cite...

* Packaging according to customer requirements(5mg, 10mg, 20mg and more). We shipped via FedEx, DHL, UPS, EMS and others courier.

According to end customer requirements, ChemFaces provide solvent format. This solvent format of product intended use: Signaling Inhibitors, Biological activities or Pharmacological activities.

Size /Price /Stock	10 mM * 1 mL in DMSO / $90.1 / In-stock
Other Packaging	*Packaging according to customer requirements(100uL/well, 200uL/well and more), and Container use Storage Tube With Screw Cap

Featured Products

More...

Purpurin

Catalog No: CFN92566
CAS No: 81-54-9
Price: $30/20mg

trans-3-Oxo-alpha-ionol

Catalog No: CFN92428
CAS No: 896107-70-3
Price: $ / mg

Diallyl disulfide

Catalog No: CFN93237
CAS No: 2179-57-9
Price: $50/20mg

Agrimol B

Catalog No: CFN98169
CAS No: 55576-66-4
Price: $138/20mg

Decursinol angelate

Catalog No: CFN93173
CAS No: 130848-06-5
Price: $ / mg

Acetyleugenol

Catalog No: CFN70222
CAS No: 93-28-7
Price: $30/20mg

L-Arginine

Catalog No: CFN90550
CAS No: 74-79-3
Price: $30/20mg

Glucoerucin

Catalog No: CFN00488
CAS No: 15592-37-7
Price: $ / mg

Licochalcone A

Catalog No: CFN99575
CAS No: 58749-22-7
Price: $88/20mg

Kaempferol 7-O-rhamnoside

Catalog No: CFN96224
CAS No: 20196-89-8
Price: $338/10mg

Description:

Sparteine is a class 1a antiarrhythmic agent, a sodium channel blocker. The deficient debrisoquine hydroxylation of Sparteine is due to the absence of P-450IID1 protein in the livers of poor metabolizers.

Targets:

P450 (e.g. CYP17)

In vitro:

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 ]

METHODS AND RESULTS:
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.
CONCLUSIONS:
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 ).

(-)-Sparteine Description

Source:	The herbs of Parochetus communis
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.

Structure Identification:

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.
METHODS AND RESULTS:
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.
CONCLUSIONS:
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).

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.
METHODS AND RESULTS:
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.
CONCLUSIONS:
This work solves a key limitation: either enantiomer of the sparteine surrogate can now be readily accessed.

Product Name	(-)-Sparteine
Price:	$218 / 10mg
CAS No.:	24915-04-6
Catalog No.:	CFN90180
Molecular Formula:	C₁₅H₂₆N₂
Molecular Weight:	234.38 g/mol
Purity:	>=98%
Type of Compound:	Alkaloids
Physical Desc.:	Powder
Source:	The herbs of Parochetus communis
Solvent:	Chloroform, Dichloromethane, Ethyl Acetate, DMSO, Acetone, etc.
Download:	COA MSDS SDF Manual
Similar structural:	Comparison (Web) (SDF)
Guestbook:

Size /Price /Stock	10 mM * 100 uL in DMSO / Inquiry / In-stock 10 mM * 1 mL in DMSO / Inquiry / In-stock
Related Libraries	Analgesia Compound Library Oxytocic Compound Library Antiarrhythmic Compound Library Alkaloids Compound Library P450 (e.g. CYP17) Inhibitor Library

	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

CFN91985	alpha-Isolupanine	486-87-3	248.36	C₁₅H₂₄N₂O
CFN98924	Lupanine	550-90-3	248.4	C₁₅H₂₄N₂O
CFN92232	13-Hydroxylupanine	15358-48-2	264.4	C₁₅H₂₄N₂O₂
CFN92233	Angustifoline	550-43-6	234.3	C₁₄H₂₂N₂O
CFN91059	Rhombifoline	529-78-2	244.34	C₁₅H₂₀N₂O
CFN99777	Sparteine sulfate pentahydrate	299-39-8	332.46	C₁₅H₂₈N₂O₄S
CFN99513	Cytisine	485-35-8	190.24	C₁₁H₁₄N₂O
CFN99776	N-Methylcytisine	486-86-2	204.27	C₁₂H₁₆N₂O
CFN91819	N-Formylcytisine	53007-06-0	218.3	C₁₂H₁₄N₂O₂
CFN91701	Acetylcytisine	6018-52-6	232.3	C₁₃H₁₆N₂O₂