140235-40-1

Basic information

• Product Name: ETHYL (3R,5S)-6-HYDROXY-3,5-O-ISO-PROPYLIDENE-3,5-DIHYDROXYHEXANOATE
• Synonyms: ETHYL (3R,5S)-6-HYDROXY-3,5-O-ISO-PROPYLIDENE-3,5-DIHYDROXYHEXANOATE;(3R,5S)-Ethyl-6-hydroxy-3,5-O-isopropylidene-3,5-dihydroxyhexanoate;2,4-Dideoxy-3,5-O-(1-methylethylidene)-D-erythrohexonic acid ethyl ester
• CAS NO: 140235-40-1
• Molecular Formula: C₁₁H₂₀O₅
• Molecular Weight: 232.27
• Mol File: 140235-40-1.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 309.8±17.0 °C(Predicted)
• Appearance: /
• Density: 1.057
• PKA: 14.25±0.10(Predicted)
• CAS DataBase Reference: ETHYL (3R,5S)-6-HYDROXY-3,5-O-ISO-PROPYLIDENE-3,5-DIHYDROXYHEXANOATE(CAS DataBase Reference)
• NIST Chemistry Reference: ETHYL (3R,5S)-6-HYDROXY-3,5-O-ISO-PROPYLIDENE-3,5-DIHYDROXYHEXANOATE(140235-40-1)
• EPA Substance Registry System: ETHYL (3R,5S)-6-HYDROXY-3,5-O-ISO-PROPYLIDENE-3,5-DIHYDROXYHEXANOATE(140235-40-1)

Safety Data

• Hazardous Substances Data: 140235-40-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
ETHYL (3R,5S)-6-HYDROXY-3,5-O-ISO-PROPYLIDENE-3,5-DIHYDROXYHEXANOATE is used as a building block in the synthesis of various drugs and pharmaceutical products. Its unique structure and reactivity make it a valuable component in the development of new medications and therapies.
Used in Medicine:
ETHYL (3R,5S)-6-HYDROXY-3,5-O-ISO-PROPYLIDENE-3,5-DIHYDROXYHEXANOATE has potential applications in the field of medicine due to its unique properties and reactivity. It may contribute to the discovery and development of new treatments and therapies for various medical conditions.
Used in Biochemistry:
This chemical compound is also used in biochemistry, where its unique structure and reactivity can be leveraged for various research purposes, such as studying enzyme mechanisms, metabolic pathways, and other biological processes.
Used in Chemical Research:
ETHYL (3R,5S)-6-HYDROXY-3,5-O-ISO-PROPYLIDENE-3,5-DIHYDROXYHEXANOATE is utilized as a reagent in organic synthesis, allowing researchers to explore its potential applications in the synthesis of new compounds and materials.
Used in Other Industrial Applications:
Beyond its use in the pharmaceutical, medical, biochemical, and chemical research fields, ETHYL (3R,5S)-6-HYDROXY-3,5-O-ISO-PROPYLIDENE-3,5-DIHYDROXYHEXANOATE may have additional industrial uses, taking advantage of its unique properties and reactivity in various processes and applications.

Upstream product

• 1245748-19-9 ethyl 3R,5S-6-(benzyloxy)-3,5-O-isopropyli-dene-3,5-dihydroxyhexanoate 
• 87319-12-8 (S)-2-(2,2-dimethyl-1,3-dioxolan-4-yl)acetic acid 
• 95422-24-5 methyl (3S)-3,4-O-isopropylidene-3,4-dihydroxybutanoate 
• 32233-44-6 2-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]acetaldehyde 
• 477541-61-0 2-(2,2-dimethyl-[1,3]dioxolan-4-yl)-1-imidazol-1-yl-ethanone 
• 94370-99-7 ethyl (S)-4-(2,2-dimethyl-1,3-dioxolan-4-yl)-3-oxobutanoate 

Relevant articles and documents

Stereoselective introduction of two chiral centers by a single diketoreductase: An efficient biocatalytic route for the synthesis of statin side chains

Statins, including atorvastatin (Lipitor), are the top-selling drugs in the world. The biocatalytic production of chiral side chains of statin drugs is of great interest to academia and industry. Stereoselective double reduction of a β,δ-diketo ester catalyzed by a diketoreductase offers a simple and efficient route for the preparation of statin side chains. Comparison of different cofactor regeneration systems resulted in an easy and cost-effective process for this enzymatic reduction.

Synthesis and highly stereoselective hydrogenation of the statin precursor ethyl (5S)-5,6-isopropylidenedioxy-3-oxohexanoate

A search for the large-scale preparation of (5S)-5,6-(isopropylidenedioxy)- 3-oxohexanoates (2) - a key intermediate in the synthesis of pharmacologially important statins - starting from (S)-malic acid is described. The synthesis of the required initial compound methyl (3S)-3,4-(isopropylidenedioxy)butanoate (1) by Moriwake's reduction of dimethyl (S)-malate (3) has been improved. Direct 2-C chain elongation of ester 1 using the lithium enolate of tert-butyl acetate has been shown to be successful at a 3- to 5-fold excess of the enolate. Unfortunately, the product, tert-butyl (5S)-5,6-(isopropylidenedioxy)-3- oxohexanoate (2a) is unstable during distillation. Ethyl (5S)-5,6- (isopropylidenedioxy)-3-oxohexanoate (2b) was prepared alternatively on a multigram scale from (3S)-3,4-(isopropylidenedioxy)butanoic acid (7) by activation with N,N′-carbonyldiimidazole and subsequent reaction with Mg(OOCCH2COOEt)2. A convenient pathway for the in situ preparation of the latter is also described. Ethyl ester (2b) can be advantageously purified by distillation. The stereochemistry of the catalytic hydrogenation of β-keto ester (2b) to ethyl (55)-5,6-(isopropylidenedioxy)- 3-hydrohyhexanoate (syn-6 and anti-6) has been studied using a number of homogeneous achiral and chiral Rh(I) and Ru(II) complexes with phosphine ligands. A comparison of Rh(I) and Ru(II) catalysts with (S)- and (R)-BINAP as chiral ligands revealed opposite activity in dependence on the polarity of the solvent. No influence of the chiral backbone of substrate 2b on the enantioselectivity was noted. A ratio of syn-6/anti-6 = 2.3 was observed with an achiral (Ph3P)3RuCl2 catalyst. Ru[(R)-Tol-BINAP]Cl2 neutralized with one equivalent of AcONa afforded the most efficient catalytic system for the production of optically pure syn-(5S)-5,6-isopropylidenedioxy-3-hydroxyhexanoate (syn-6) at a preparative substrate/catalyst ratio of 1000:1.

2,4-DIHYDROXYADIPIC ACID DERIVATIVE

A novel 2,4-dihydroxyadipic acid derivative of the formula: STR1 wherein R1 and R4 are the same or different and each a hydrogen atom, an alkyl group, an aralkyl group, an aryl group or a silyl group, and R2 and R3 are the same or different and each a hydrogen atom or a protective group of a hydroxy group or together form a ring, which is useful as a common intermediate in the synthesis of HMG-CoA reductase inhibitor