(S)-(-)-WARFARIN

Base Information

• Chemical Name: (S)-(-)-WARFARIN
• CAS No.: 5543-57-7
• Molecular Formula: C₁₉H₁₆O₄
• Molecular Weight: 308.334
• Mol file: 5543-57-7.mol

Synonyms:2H-1-Benzopyran-2-one,4-hydroxy-3-(3-oxo-1-phenylbutyl)-, (S)-; Coumarin, 3-(a-acetonylbenzyl)-4-hydroxy-,(S)-(-)- (8CI); (-)-Warfarin; (S)-Warfarin;4-Hydroxy-3-[(1S)-3-oxo-1-phenylbutyl]-2H-1-benzopyran-2-one

Chemical Property of (S)-(-)-WARFARIN

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: ≥170 °C
• Boiling Point: 471.1°Cat760mmHg
• Flash Point: 170.3°C
• PSA: 67.51000
• Density: 1.307g/cm³
• LogP: 3.60960
• Storage Temp.: 2-8°C

Purity/Quality:

98%,99%, ^*data from raw suppliers

S-(-)-Warfarin ^*data from reagent suppliers

Safty Information:

• Hazard Codes: T
• Statements: 61-48/25-52/53
• Safety Statements: 53-45-61

MSDS Files:

Useful:

• Description: (–)-Warfarin is a component of (±)-warfarin . It is an anticoagulant that interferes with interconversion of vitamin K and vitamin K epoxide and the role of vitamin K in carboxylation of several clotting cascade proteins, inhibiting the initiation of clotting. In vivo, (–)-warfarin slows formation of the prothrombin complex and exhibits 6.6-fold more potent anticoagulant activity than (+)-warfarin in rats. (–)-Warfarin is primarily metabolized by the cytochrome P450 (CYP) isoform CYP2C9 and genetic polymorphisms in this enyzme, as well as other compounds metabolized by CYP2C9, increase the potential for catastrophic bleeding complications. Formulations containing warfarin have been used to treat and prevent blood clots in atrial fibrillation, heart valve replacement, venous thrombosis, and pulmonary embolism.
• Uses: The S-(-)-form of Warfarin (W498500). Coumarin anticoagulant. (S)-(?)-Warfarin has been used in cell cultures.

Technology Process of (S)-(-)-WARFARIN

There total 48 articles about (S)-(-)-WARFARIN which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

(S)-4-Methoxywarfarin (60431-20-1) → S-(-)-warfarin (81-81-2,5543-56-6,5543-57-7,5543-58-8)

Guidance literature:

With boron tribromide; In dichloromethane; at 0 - 25 ℃; for 6h;

DOI:10.1021/ol0619157

Reference yield: 94.0%

4-hydroxy[1]benzopyran-2-one (1076-38-6,92395-12-5) + 1-Phenylbut-1-en-3-one (122-57-6) → R-warfarin (81-81-2,5543-56-6,5543-57-7,5543-58-8) + S-(-)-warfarin (81-81-2,5543-56-6,5543-57-7,5543-58-8)

Guidance literature:

With (1R,2R)-1,2-cyclohexanediamine-MIL-4; In tetrahydrofuran; at 10 ℃; for 96h; Solvent; Reagent/catalyst; enantioselective reaction;

DOI:10.1002/adsc.201300554

Reference yield: 94.0%

4-hydroxy[1]benzopyran-2-one (1076-38-6,92395-12-5) + 1-Phenylbut-1-en-3-one (122-57-6) → R-warfarin (81-81-2,5543-56-6,5543-57-7,5543-58-8) + S-(-)-warfarin (81-81-2,5543-56-6,5543-57-7,5543-58-8)

Guidance literature:

With (1R,2R)-1,2-cyclohexanediamine-MIL-4; In tetrahydrofuran; at 10 ℃; for 96h; Solvent; Reagent/catalyst; enantioselective reaction;

DOI:10.1002/adsc.201300554

upstream raw materials:

warfarin

dehydrowarfarin

4-hydroxy[1]benzopyran-2-one

(E)-benzalacetone

Downstream raw materials:

[13C]-S,S-Warfarin alcohol

[13C]-S,R-Warfarin alcohol

[14C]-R,S-Warfarin alcohol

[14C]-R,R-Warfarin alcohol

Refernces

• 1、 Shahnani, Mostafa,Sefidbakht, Yahya,Maghari, Shokoofeh,Mehdi, Ahmad,Rezadoost, Hassan,Ghassempour, Alireza. "Enantioseparation of mandelic acid on vancomycin column: Experimental and docking study". supporting information. p. 1289 - 1298. Retrieved 2020/08/19.
• 2、 Arunachalam, Rajendran,Chinnaraja, Eswaran,Natarajan, Ramalingam,Samanta, Krishanu,Subramanian, Palani S.. "Enantioselective Michael Addition Reaction Catalysed by Enantiopure Binuclear Nickel(II) Close-Ended Helicates". . . Retrieved 2020/02/04.