154026-92-3

Basic information

• Product Name: TERT-BUTYL (S)-6-CHLORO-5-HYDROXY-3-OXOHEXANOATE
• Synonyms: TERT-BUTYL (S)-6-CHLORO-5-HYDROXY-3-OXOHEXANOATE;Tert-Butyl 6-chloro-5(S)-hydroxy-3-oxohexanoate
• CAS NO: 154026-92-3
• Molecular Formula: C₁₀H₁₇ClO₄
• Molecular Weight: 236.69
• Mol File: 154026-92-3.mol
• Article Data: 11

Chemical Properties

• Appearance: /
• Storage Temp.: Hygroscopic, -20°C Freezer, Under inert atmosphere
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• Stability: Hygroscopic
• CAS DataBase Reference: TERT-BUTYL (S)-6-CHLORO-5-HYDROXY-3-OXOHEXANOATE(CAS DataBase Reference)
• NIST Chemistry Reference: TERT-BUTYL (S)-6-CHLORO-5-HYDROXY-3-OXOHEXANOATE(154026-92-3)
• EPA Substance Registry System: TERT-BUTYL (S)-6-CHLORO-5-HYDROXY-3-OXOHEXANOATE(154026-92-3)

Safety Data

• Hazardous Substances Data: 154026-92-3(Hazardous Substances Data)

Usage

Description

TERT-BUTYL (S)-6-CHLORO-5-HYDROXY-3-OXOHEXANOATE is an organic compound that serves as an intermediate in the synthesis of various pharmaceuticals, particularly statins or HMG-CoA reductase inhibitors. These inhibitors are widely used to lower cholesterol levels and manage cardiovascular diseases.

Uses

Used in Pharmaceutical Industry:
TERT-BUTYL (S)-6-CHLORO-5-HYDROXY-3-OXOHEXANOATE is used as a key intermediate in the synthesis of statins for the treatment of high cholesterol and related cardiovascular conditions. Its role in the production of these drugs is crucial, as it contributes to the development of HMG-CoA reductase inhibitors, which help regulate cholesterol levels in the body.
Additionally, TERT-BUTYL (S)-6-CHLORO-5-HYDROXY-3-OXOHEXANOATE may have potential applications in other industries, such as the development of new drugs or chemical compounds, but the provided materials do not specify these uses.

Upstream product

• 276249-18-4 tert-butyl 6-chloro-3,5-dioxohexanoate 
• 5292-43-3 bromoacetic acid tert-butyl ester 
• 727382-14-1 (3S)-4-chloro-3-[(trimethylsilyl)oxy]butyronitrile 
• 1694-31-1 tert-butyl acetoacetate 
• 540-88-5 acetic acid tert-butyl ester 
• 10488-69-4 ethyl (S)-4-chloro-3-hydroxybutanoate 
• 50364-40-4 2-bromo-2-tert-butyl acetic acid 

Downstream Products

• 154026-93-4 1,1-dimethylethyl (3R,5S)-6-chloro-3,5-dihydroxy-4-hexanoate 
• 135999-61-0 (S)-6-chloromethyl-5,6-dihydropyran-2-one 
• 122046-62-2 (S)-goniothalamin 
• 190835-53-1 (+)-(S)-2-(trans-β-styryl)-2,3-dihydro-pyran-4-one 
• 154026-94-5 (4R-cis)-6-(chloromethyl)-2,2-dimethyl-1,3-dioxane-4-acetic acid,1,1-dimethylethyl ester 
• 521973-99-9 tert-butyl 2-((4S,6S)-6-(chloromethyl)-2,2-dimethyl-1,3-dioxan-4-yl)acetate 
• 154026-95-6 (4R-cis)-6-[(acetyloxy)methyl]-2,2-dimethyl-1,3-dioxane-4-acetic acid tert-butyl ester 
• 124655-09-0 1,1-dimethylethyl (4R-cis)-6-hydroxymethyl-2,2-dimethyl-1,3-dioxane-4-acetate 
• 124752-23-4 tert-butyl 2-[(4R,6S)-6-formyl-2,2-dimethyl-1,3-dioxan-4-yl]acetate 
• 147489-06-3 (4R,6S)-(E)-{6-[2-(2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl)-vinyl]-2,2-dimethyl-1,3-dioxan-4-yl}acetic acid tert-butyl ester 
• 355806-00-7 rosuvastatin tert-butyl ester 
• 586966-54-3 (3R,5S,6E)-7-[2-cyclopropyl-4-(4-fluorophenyl)-3-quinolyl]-3,5-dihydroxy-6-heptenoic acid tert-butyl ester 
• 147526-32-7 pitavastatin calcium salt 

Relevant articles and documents

Regio and enantioselective reduction of t-butyl 6-chloro-3,5-dioxohexanoate with baker's yeast

Whole baker's yeast cells reduce t-butyl 6-chloro-3,5-dioxohexanoate regioselectively to the corresponding C5 hydroxy keto ester. While the (R)-alcohol was favored, the enantioselectivity was poor (41% ee). A variety of process conditions were evaluated in order to improve both the enantioselectivity and yield of this reduction. Including a nonpolar resin in the reaction mixture afforded the (R)-alcohol in 94% ee and 50% isolated yield. The enantioselectivity was further improved to >99% ee by substituting purified YGL157w in place of whole yeast cells. This reductase was identified by screening a collection of yeast enzymes uncovered by genome sequence analysis.

NOVEL BORONATE ETHER INTERMEDIATES FOR PREPARATION OF STATIN COMPOUNDS, PREPARATION METHOD THEREOF AND PREPARATION METHOD OF STATIN COMPOUNDS USING SAID BORONATE ETHER INTERMEDIATES

The present invention relates to a novel boronate ether compound and a manufacturing method thereof. Provided is a novel boronate ether compound denoted by chemical formula 1 or chemical formula 2 as an intermediate to manufacture rosuvastatin calcium or pitavastatin calcium which is one of the statin based compounds to reduce the level of low density lipoprotein (LDL) of patients who have hyperlipidemia and are accordingly cured, and statin compounds with high purity are easily manufactured and separated compared with an existing patented method and are easily provided in a method of mass production.

A NOVEL, GREEN AND COST EFFECTIVE PROCESS FOR SYNTHESIS OF TERT-BUTYL (3R,5S)-6-OXO-3,5-DIHYDROXY-3,5-O-ISOPROPYLIDENE-HEXANOATE

The present invention provides a process of preparation of an intermediate useful for the preparation of statins more particularly the present invention relates to an eco-friendly and cost effective process for the preparation of tert -butyl (3R,5S)-6-oxo-3,5-dihydroxy- 3,5-O-isopropylidene-hexanoate [I].