2,2-DiMethylbutanoic Acid (1S,6S,7R,8S,8aR)-1,2,6,7,8,8a-Hexahydro-6-hydroperoxy-3,7-diMethyl-8-[2-[(2R,4R)-tetrahydro-4-hydroxy-6-oxo-2H-pyran-2-yl]ethyl]-1-naphthalenyl Ester

Base Information

• Chemical Name: 2,2-DiMethylbutanoic Acid (1S,6S,7R,8S,8aR)-1,2,6,7,8,8a-Hexahydro-6-hydroperoxy-3,7-diMethyl-8-[2-[(2R,4R)-tetrahydro-4-hydroxy-6-oxo-2H-pyran-2-yl]ethyl]-1-naphthalenyl Ester
• CAS No.: 149949-01-9
• Molecular Formula: C₂₅H₃₈O₇
• Molecular Weight: 450.573
• Mol file: 149949-01-9.mol

Synonyms:

Chemical Property of 2,2-DiMethylbutanoic Acid (1S,6S,7R,8S,8aR)-1,2,6,7,8,8a-Hexahydro-6-hydroperoxy-3,7-diMethyl-8-[2-[(2R,4R)-tetrahydro-4-hydroxy-6-oxo-2H-pyran-2-yl]ethyl]-1-naphthalenyl Ester

Chemical Property:

• Boiling Point: 626.5±55.0 °C(Predicted)
• PKA: 11.25±0.70(Predicted)
• Density: 1.18±0.1 g/cm3(Predicted)

Purity/Quality:

>95% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: 6(S)-Hydroperoxy Simvastatin is the oxidative degradation product of Simvastatin (S485000).

Technology Process of 2,2-DiMethylbutanoic Acid (1S,6S,7R,8S,8aR)-1,2,6,7,8,8a-Hexahydro-6-hydroperoxy-3,7-diMethyl-8-[2-[(2R,4R)-tetrahydro-4-hydroxy-6-oxo-2H-pyran-2-yl]ethyl]-1-naphthalenyl Ester

There total 2 articles about 2,2-DiMethylbutanoic Acid (1S,6S,7R,8S,8aR)-1,2,6,7,8,8a-Hexahydro-6-hydroperoxy-3,7-diMethyl-8-[2-[(2R,4R)-tetrahydro-4-hydroxy-6-oxo-2H-pyran-2-yl]ethyl]-1-naphthalenyl Ester 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:

simvastatin (123049-81-0,79902-63-9) → 2,2-Dimethyl-butyric acid (2R,4S,4aS,5S,6S)-5-[2-((2R,4R)-4-hydroxy-6-oxo-tetrahydro-pyran-2-yl)-ethyl]-2,6-dimethyl-2,3,4,4a,5,6-hexahydro-1aH-1-oxa-cyclopropa[d]naphthalen-4-yl ester + 6(S)-hydroperoxysimvastatin (149949-01-9) + 2,2-Dimethyl-butyric acid (1S,3R,4S)-4-hydroxy-8-[2-((2R,4R)-4-hydroxy-6-oxo-tetrahydro-pyran-2-yl)-ethyl]-3,7-dimethyl-1,2,3,4-tetrahydro-naphthalen-1-yl ester + 6(R)-<2-<8(S)-((2,2-Dimethylbutyryl)oxy)-2(S),6-dimethyl-3-oxo-1,2,3,7,8,8a(R)-hexahydronaphth-1(S)-yl>ethyl>-4(R)-hydroxy-3,4,5,6-tetrahydro-2H-pyran-2-one + 2,2-Dimethyl-butyric acid (1S,3R,4S,7S,8S)-4-hydroxy-8-[2-((2R,4R)-4-hydroxy-6-oxo-tetrahydro-pyran-2-yl)-ethyl]-3,7-dimethyl-1,2,3,4,7,8-hexahydro-naphthalen-1-yl ester (149949-05-3) + 2,2-Dimethyl-butyric acid (4S,4aS,5S,6S)-2-hydroperoxy-5-[2-((2R,4R)-4-hydroxy-6-oxo-tetrahydro-pyran-2-yl)-ethyl]-2,6-dimethyl-2,3,4,4a,5,6-hexahydro-1aH-1-oxa-cyclopropa[d]naphthalen-4-yl ester

Guidance literature:

With 2,2’-azobis(4-methoxy-2,4-dimethyl)valeronitrile; oxygen; In 1,2-dichloro-ethane; at 35 ℃; for 6h; Kinetics; Mechanism; Product distribution;

DOI:10.1016/S0040-4020(01)81275-8

Reference yield:

simvastatin (123049-81-0,79902-63-9) → 3(S)-hydroperoxysimvastatin (1092716-44-3) + 3(R)-hydroperoxysimvastatin (1092716-42-1) + 6(S)-hydroxysimvastatin (133645-46-2) + 6(S)-hydroperoxysimvastatin (149949-01-9)

Guidance literature:

With butylated hydroxy-anysole; oxygen; at 50 ℃; for 216 - 384h; Reactivity;

Reference yield:

6(S)-hydroperoxysimvastatin (149949-01-9) → 6(S)-hydroxysimvastatin (133645-46-2)

Guidance literature:

With sodium tetrahydroborate; In acetonitrile; for 2h; Ambient temperature;

DOI:10.1016/S0040-4020(01)81275-8

upstream raw materials:

simvastatin

Downstream raw materials:

6(S)-hydroxysimvastatin

Refernces

• 1、 Smith,DiMichele,Colwell Jr.,Dezeny,Douglas,Reamer,Verhoeven. "Autooxidation of simvastatin". . p. 4447 - 4462. Retrieved 2007/10/02.