Tenivastatin ammonium

Base Information

• Chemical Name: Tenivastatin ammonium
• CAS No.: 139893-43-9
• Molecular Formula: C25H40O6^.NH3
• Molecular Weight: 453.62
• European Community (EC) Number: 404-520-2,604-165-5,658-040-5
• UNII: 76RD797JAX
• DSSTox Substance ID: DTXSID60449890
• Mol file: 139893-43-9.mol

Synonyms:Simvastatin ammonium salt;Tenivastatin ammonium;139893-43-9;UNII-76RD797JAX;76RD797JAX;EC 604-165-5;Simvastatin acid (ammonium);Simvastatin Hydroxy Acid, Ammonium Salt;1-Naphthaleneheptanoic acid, 8-(2,2-dimethyl-1-oxobutoxy)-1,2,6,7,8,8a-hexahydro-b,D-dihydroxy-2,6-dimethyl-, monoammonium salt, (br,dr,1S,2S,6R,8S,8aR)- (9ci);Tenivastatin (ammonium);Ammonium (3R,5R)-7-[(1S,2S,6R,8S,8aR)-8-(2,2-dimethylbutanoyloxy)-2,6-dimethyl-1,2,6,7,8,8a-hexahydronaphthalen-1-yl]-3,5-dihydroxyheptanoate;Simvastatin acid ammonium salt;Ammonium simvastatin;Simvastatinammoniumsalt;Simvastatin Carboxylic Acid Ammonium Salt;(3R,5R)-7-[(1S,2S,6R,8S,8aR)-8-[(2,2-Dimethylbutanoyl)oxy]-2,6-dimethyl-1,2,6,7,8,8a-hexahydronaphthalen-1-yl]-3,5-dihydroxyheptanoic Acid Ammonium Salt (Tenivastatin Ammonium Salt);ammonium 7-(2,6-dimethyl-8-(2,2-dimethylbutyryloxy)-1,2,6,7,8,8a-hexahydro-1-naphthyl)-3,5-dihydroxyheptanoate;SCHEMBL2987588;DTXSID60449890;FFPDWNBTEIXJJF-OKDJMAGBSA-N;HY-119695A;CS-0079236;A885934;J-007330;(3R,5R)-7-((1S,2S,6R,8S,8aR)-8-(2,2-Dimethylbutanoyloxy)-2,6-dimethyl-1,2,6,7,8,8a-hexahydronaphthalen-1-yl)-3,5-dihydroxyheptanoate ammonium salt;(betaR,deltaR,1S,2S,6R,8S,8aR)-8-(2,2-Dimethyl-1-oxobutoxy)-1,2,6,7,8,8a-hexahydro-beta,delta-dihydroxy-2,6-dimethyl-1-naphthaleneheptanoic Acid Ammonium Salt;1-Naphthaleneheptanoic acid, 8-(2,2-dimethyl-1-oxobutoxy)-1,2,6,7,8,8a-hexahydro-.beta.,.delta.-dihydroxy-2,6-dimethyl-, ammonium salt (1:1), (.beta.R,.delta.R,1S,2S,6R,8S,8aR)-;Azane;7-[8-(2,2-dimethylbutanoyloxy)-2,6-dimethyl-1,2,6,7,8,8a-hexahydronaphthalen-1-yl]-3,5-dihydroxyheptanoic acid;azanium;(3R,5R)-7-[(1S,2S,6R,8S,8aR)-8-(2,2-dimethylbutanoyloxy)-2,6-dimethyl-1,2,6,7,8,8a-hexahydronaphthalen-1-yl]-3,5-dihydroxyheptanoate

Chemical Property of Tenivastatin ammonium

Chemical Property:

• Vapor Pressure: 0.001Pa at 25℃
• Melting Point: 128-131°C
• PSA: 107.30000
• LogP: 4.42960
• Storage Temp.: Hygroscopic, -20?C Freezer, Under Inert Atmosphere
• Solubility.: DMSO (Sparingly), Ethanol (Slightly), Methanol (Slightly), Water (Slightly)
• Water Solubility.: 3.3g/L at 20℃
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 10
• Exact Mass: 453.30903809
• Heavy Atom Count: 32
• Complexity: 689

Purity/Quality:

99% ^*data from raw suppliers

Simvastatin Hydroxy Acid, Ammonium Salt ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi,T
• Statements: 36/37/38-64-52/53-40-61
• Safety Statements: 26-36-36/37/39-24/25-22-53

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC(C)(C)C(=O)OC1CC(C=C2C1C(C(C=C2)C)CCC(CC(CC(=O)[O-])O)O)C.[NH4+]
• Isomeric SMILES: CCC(C)(C)C(=O)O[C@H]1C[C@H](C=C2[C@H]1[C@H]([C@H](C=C2)C)CC[C@H](C[C@H](CC(=O)[O-])O)O)C.[NH4+]
• Uses: A competitive inhibitor of HMG-CoA reductase. A metabolite of Simvastin A metabolite of Simvastin (S485000). A competitive inhibitor of HMG-CoA reductase.

Technology Process of Tenivastatin ammonium

There total 17 articles about Tenivastatin ammonium 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: 97.6%

N-cyclopropyl-7-[1,2,6,7,8,8a(R)-hexahydro-2(S),6(R)-dimethyl-8(S)-[2,2-dimethylbutanoyl]oxy-1(S)-naphthyl]-3(R),5(R)-dihydroxyheptanoic acid amide + C29H47NO5 → simvastatin ammonium salt (139893-43-9)

Guidance literature:

N-cyclopropyl-7-[1,2,6,7,8,8a(R)-hexahydro-2(S),6(R)-dimethyl-8(S)-[2,2-dimethylbutanoyl]oxy-1(S)-naphthyl]-3(R),5(R)-dihydroxyheptanoic acid amide; C₂₉H₄₇NO₅; With sodium hydroxide; In methanol; at 75 - 78 ℃; for 3h; Inert atmosphere;

With hydrogenchloride; In methanol; water; for 10 - 15h; pH=4; Inert atmosphere;

With ammonium hydroxide; In methanol; at 22 - 25 ℃; for 1.5h; Inert atmosphere;

DOI:10.1021/op990187i

Reference yield: 87.0%

N-butyl-7-<1,2,6,7,8,8a(R)-hexahydro-2(S),6(R)-dimethyl-8(S)-<<2,2-dimethylbutanoyl>oxy>-1(S)-naphthyl>-3(R),5(R)-dihydroxyheptanoic acid amide (134970-33-5) → simvastatin ammonium salt (139893-43-9)

Guidance literature:

N-butyl-7-<1,2,6,7,8,8a(R)-hexahydro-2(S),6(R)-dimethyl-8(S)-<<2,2-dimethylbutanoyl>oxy>-1(S)-naphthyl>-3(R),5(R)-dihydroxyheptanoic acid amide; With sodium hydroxide; In water; at 77 ℃; for 4h;

With hydrogenchloride; In water; at 15 ℃; pH=4.7;

With ammonium hydroxide; In methanol; at 28 ℃; for 0.5h;

DOI:10.1080/00397910802369570

Reference yield: 86.4%

C10H18O3S + (3R,5R)-3,5-dihydroxy-7-((1S,2S,6R,8S,8aR)-8-hydroxy-2,6-dimethyl-1,2,6,7,8,8a-hexahydronaphthalen-1-yl)heptanoic acid (132748-10-8) → simvastatin ammonium salt (139893-43-9)

Guidance literature:

With hydrogenchloride; ammonia; In water; for 50h; pH=9.5 - 9.8;

upstream raw materials:

N-butyl-7-<1,2,6,7,8,8a(R)-hexahydro-2(S),6(R)-dimethyl-8(S)-<<2,2-dimethylbutanoyl>oxy>-1(S)-naphthyl>-3(R),5(R)-dihydroxyheptanoic acid amide

N-butyl-7-<1,2,6,7,8,8a(R)-hexahydro-2(S),6(R)-dimethyl-8(S)-<<2,2-dimethylbutanoyl>oxy>-1(S)-naphthyl>-3(R),5(R)-bis<(tert-butyldimethylsilyl)oxy>heptanoic acid amide

N-benzyl-7-[1,2,6,7,8,8a(R)-hexahydro-2(S),6(R)-dimethyl-8(S)-[[2,2-dimethylbutanoyl]oxy]-1(S)naphthyl]-3(R),5(R)-bis[(tert-butyldimethylsilyl)oxy]heptanoic acid amide

simvastatin acetate

Downstream raw materials:

C₅₀H₇₆O₁₀

simvastatin

simvastatin acid

Refernces

• 1、 -. "Lov-D acyltransferase mediated acylation". . . Retrieved 2016/08/17.
• 2、 -. "ISOLATION AND RECOVERY OF SIMVASTATIN IN LACTONE FORM OR IN THE FORM OF AN ACID SALT FROM THE HARVESTED FERMENTATION BROTH". Page/Page column 3; 4. . Retrieved 2009/07/03.