(3S,4S)-4-azaniumyl-3-hydroxy-6-methylheptanoate

Base Information

• Chemical Name: (3S,4S)-4-azaniumyl-3-hydroxy-6-methylheptanoate
• CAS No.: 49642-07-1
• Molecular Formula: C8H17NO3
• Molecular Weight: 175.228
• Hs Code.: 2922509090
• Mol file: 49642-07-1.mol

Synonyms:

Chemical Property of (3S,4S)-4-azaniumyl-3-hydroxy-6-methylheptanoate

Chemical Property:

• Appearance/Colour: white powder
• Vapor Pressure: 1.83E-06mmHg at 25°C
• Melting Point: 209 °C
• Refractive Index: 1.49
• Boiling Point: 355.1 °C at 760 mmHg
• PKA: 3.97±0.10(Predicted)
• Flash Point: 168.5 °C
• PSA: 83.55000
• Density: 1.112 g/cm³
• LogP: 0.89570
• Storage Temp.: 2-8°C
• Solubility.: 0.5 M HCl: 50 mg/mL, clear, very faintly yellow
• XLogP3: -1.7
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 175.12084340
• Heavy Atom Count: 12
• Complexity: 142

Purity/Quality:

98%Min ^*data from raw suppliers

STATINE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(C)CC(C(CC(=O)[O-])O)[NH3+]
• Isomeric SMILES: CC(C)C[C@@H]([C@H](CC(=O)[O-])O)[NH3+]
• Clinical Use: With the possible exception of atorvastatin, the statins are used to lower LDL cholesterol in familial or polygenic ( multifactorial) hypercholesterolemia (type IIa) and in combination with triglyceride-lowering drugs to treat combined hyperlipidemia (type IIb) when both LDL and VLDL (very low density lipoproteins) are elevated. However, the statins probably should not be given with the fibrates (triglyceridelowering drugs, discussed later), since this combination may greatly increase statin toxicity. Atorvastatin, the most potent of the available statins, has also been shown to lower blood triglycerides significantly. This effect may be due to decreasing hepatic cholesterol and cholesterol ester levels to such an extent that hepatic formation of VLDL is impaired.The statins also have been claimed to reduce blood cholesterol levels modestly in some patients with homozygous familial hypercholesterolemia, a condition often fatal in childhood or in early adulthood. The statins may lower the risk of CHD by decreasing inflammation, an important component of atherogenesis. Lovastatin decreased elevated plasma levels of Creactive protein, a marker for cellular inflammation, and acute coronary events in patients with relatively low plasma cholesterol levels. Recent studies also suggest that use of statins may decrease the risk of stroke, dementia, and Alzheimer’s disease and may improve bone density in postmenopausal women. These broad actions may be related to the hypocholesterolemic, antiproliferative, antiinflammatory, or antioxidant properties of the statins or some combination of these properties.

Technology Process of (3S,4S)-4-azaniumyl-3-hydroxy-6-methylheptanoate

There total 96 articles about (3S,4S)-4-azaniumyl-3-hydroxy-6-methylheptanoate 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: 88.0%

methyl (3S,4S)-3-hydroxy-6-methyl-4-(isopropoxycarbonyl)aminoheptanoate (128625-47-8) → statine (49642-07-1)

Guidance literature:

With hydrogenchloride; In ethyl acetate; at 100 ℃;

DOI:10.1016/S0040-4039(00)94374-0

Reference yield: 88.0%

(3S,4S)-4-(N,N-dibenzylamino)-3-hydroxy-6-methylheptanoic acid (390377-64-7) → statine (49642-07-1)

Guidance literature:

With hydrogen; palladium hydroxide - carbon; In methanol; water; for 2h;

DOI:10.1016/S0040-4020(01)00804-3

Reference yield: 85.0%

(3S,4S)-4-azido-3-hydroxy-6-methylheptanoic acid (55714-49-3) → statine (49642-07-1)

Guidance literature:

With hydrogen; palladium on activated charcoal; In acetic acid; at 40 ℃; for 2.5h; under 760 Torr;

DOI:10.1246/cl.1999.687

upstream raw materials:

(3aR,5S,6aR)-5-((S)-1-Azido-3-methyl-butyl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxole

(3S,4S)-4-azido-3-hydroxy-6-methylheptanoic acid

(3S,4S)-4-(tert-butoxycarbonylamino)-3-hydroxy-6-methylheptanoic acid

(4S,5S)-5-isobutyl-4-hydroxy-2-oxopyrrolidine

Downstream raw materials:

(2E)-N-Isobutyl-3-<(4S,5S)-3-benzyloxycarbonyl-4-isobutyl-2,2-dimethyl-5-oxazolidinyl>-2-ethyl-2-propenamide

(2Z)-N-Isobutyl-3-<(4S,5S)-3-benzyloxycarbonyl-4-isobutyl-2,2-dimethyl-5-oxazolidinyl>-2-ethyl-2-propenamide

(4S,5S)-5-((E)-2-Ethoxycarbonyl-4-phenyl-but-1-enyl)-4-isobutyl-2,2-dimethyl-oxazolidine-3-carboxylic acid benzyl ester

(4S,5S)-5-((E)-3-Cyclohexyl-2-ethoxycarbonyl-propenyl)-4-isobutyl-2,2-dimethyl-oxazolidine-3-carboxylic acid benzyl ester

Refernces

• 1、 Chen, Ming-Hua,Chang, Shan-Shan,Dong, Biao,Yu, Li-Yan,Wu, Ye-Xiang,Wang, Ren-Zhong,Jiang, Wei,Gao, Zeng-Ping,Si, Shu-Yi. "Ahmpatinin iBu, a new HIV-1 protease inhibitor, from Streptomyces sp. CPCC 202950?". . p. 5138 - 5144. Retrieved 2018.
• 2、 Yoo, Dongwon,Oh, Joon Seok,Kim, Young Gyu. "The N-hydroxymethyl group for stereoselective conjugate addition: application to the synthesis of (-)-statine.". . p. 1213 - 1215. Retrieved 2002.
• 3、 Chang, Meng-Yang,Kung, Yung-Hua,Chen, Shui-Tein. "Regioselective Baeyer-Villiger lactonization of 2-substituted pyrrolidin-4-one. Synthesis of statine". . p. 4865 - 4870. Retrieved 2007/10/03.