(βR,δR,1S,2S)-1,2-Dihydro-β,δ,6-trihydroxy-2-methyl-1-naphthaleneheptanoic Acid (Pravastatin Impurity)

Base Information

• Chemical Name: (βR,δR,1S,2S)-1,2-Dihydro-β,δ,6-trihydroxy-2-methyl-1-naphthaleneheptanoic Acid (Pravastatin Impurity)
• CAS No.: 136590-28-8
• Molecular Formula: C₁₈H₂₄O₅
• Molecular Weight: 320.386
• Mol file: 136590-28-8.mol

Synonyms:(βR,δR,1S,2S)-1,2-Dihydro-β,δ,6-trihydroxy-2-methyl-1-naphthaleneheptanoic Acid (Pravastatin Impurity);(βR,δR,1S,2S)-1,2-Dihydro-β,δ,6-trihydroxy-2-Methyl-1-naphthaleneheptanoic Acid SodiuM Salt (Pravastatin IMpurity);Pravastatin IMpurity G

Chemical Property of (βR,δR,1S,2S)-1,2-Dihydro-β,δ,6-trihydroxy-2-methyl-1-naphthaleneheptanoic Acid (Pravastatin Impurity)

Chemical Property:

• PSA: 100.82000
• LogP: 2.94370
• Storage Temp.: -20°C Freezer, Under Inert Atmosphere
• Solubility.: DMSO (Slightly), Methanol (Slightly), Water (Slightly)

Purity/Quality:

97% ^*data from raw suppliers

(βR,deltaR,1S,2S)-1,2-Dihydro-β,delta,6-trihydroxy-2-methyl-1-naphthaleneheptanoicAcidSodiumSalt(PravastatinImpurity) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Pravastatin impurity.

Technology Process of (βR,δR,1S,2S)-1,2-Dihydro-β,δ,6-trihydroxy-2-methyl-1-naphthaleneheptanoic Acid (Pravastatin Impurity)

There total 5 articles about (βR,δR,1S,2S)-1,2-Dihydro-β,δ,6-trihydroxy-2-methyl-1-naphthaleneheptanoic Acid (Pravastatin Impurity) 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:

(S)-2-Methyl-butyric acid (1S,7S,8S,8aR)-8-[2-((2R,4R)-4-hydroxy-6-oxo-tetrahydro-pyran-2-yl)-ethyl]-7-methyl-3-oxo-1,2,3,7,8,8a-hexahydro-naphthalen-1-yl ester → R-195 (136590-28-8)

Guidance literature:

With water; sodium hydroxide; In acetone; at 0 - 5 ℃; for 1h; Solvent;

Reference yield:

(S)-2-Methyl-butyric acid (1S,7S,8S,8aR)-8-[2-((2R,4R)-4-hydroxy-6-oxo-tetrahydro-pyran-2-yl)-ethyl]-7-methyl-3-oxo-1,2,3,7,8,8a-hexahydro-naphthalen-1-yl ester → R-195 (136590-28-8) + R-104 (201423-59-8)

Guidance literature:

With sodium hydroxide; In acetonitrile; at 0 ℃; for 0.25h;

DOI:10.1248/bpb.20.1199

Reference yield:

pravastatin sodium salt (81131-70-6,81176-41-2,124917-23-3) → R-195 (136590-28-8)

Guidance literature:

Multi-step reaction with 3 steps

1: hydrogenchloride / ethyl acetate; water; toluene / 3 h / 0 - 5 °C / pH 2 - 3 / Reflux

2: silica gel; pyridinium chlorochromate / dichloromethane / 2 h / 0 - 5 °C

3: water; sodium hydroxide / acetone / 1 h / 0 - 5 °C

With hydrogenchloride; water; silica gel; pyridinium chlorochromate; sodium hydroxide; In dichloromethane; water; ethyl acetate; acetone; toluene;

upstream raw materials:

pravastatin sodium salt

pravastatin lactone

Refernces

• 1、 Muramatsu, Shigeki,Komokata, Yuko,Tanaka, Yorihisa,Takahagi, Hidekuni. "Metabolism of pravastatin sodium by 3α-hydroxysteroid dehydrogenase". . p. 1199 - 1203. Retrieved 1997.