109721-08-6

Basic information

• Product Name: (S)-3-[[(1,1-Dimethyl)dimethylsily]oxy]pentanedioic acid monomethyl ester
• Synonyms: (S)-3-[[(1,1-Dimethyl)dimethylsily]oxy]pentanedioic acid monomethyl ester
• CAS NO: 109721-08-6
• Molecular Formula: C₁₂H₂₄O₅Si
• Molecular Weight: 248.3483
• Mol File: 109721-08-6.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (S)-3-[[(1,1-Dimethyl)dimethylsily]oxy]pentanedioic acid monomethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-3-[[(1,1-Dimethyl)dimethylsily]oxy]pentanedioic acid monomethyl ester(109721-08-6)
• EPA Substance Registry System: (S)-3-[[(1,1-Dimethyl)dimethylsily]oxy]pentanedioic acid monomethyl ester(109721-08-6)

Safety Data

• Hazardous Substances Data: 109721-08-6(Hazardous Substances Data)

Usage

General Description

(S)-3-[[(1,1-Dimethyl)dimethylsily]oxy]pentanedioic acid monomethyl ester, also known as dimethyl methylsilanediol, is a chemical compound with the molecular formula C9H20O5Si. It is an ester derivative of pentanedioic acid and is commonly used in the synthesis of pharmaceuticals and agrochemicals. (S)-3-[[(1,1-Dimethyl)dimethylsily]oxy]pentanedioic acid monomethyl ester has a wide range of applications in organic synthesis due to its ability to act as a protective group for carboxylic acids during chemical reactions. It is also used as a reagent in the preparation of various compounds for medicinal and industrial purposes. Additionally, it is a key component in the production of silicone polymers, which are widely used in industries such as automotive, construction, and electronics.

Upstream product

• 90613-44-8 methyl 3-acetoxypentanedioate 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 67-56-1 methanol 
• 91424-40-7 3-(tert-butyldimethylsilyloxy)glutaric anhydride 

Downstream Products

• 205647-21-8 (3R)-[(tert-butyldimethylsilyl)oxy]-7-[4-(4-fluorophenyl)-2-isopropyl-5-methyl-1H-pyrrol-3-yl]-6-(methanesulfinyl)-5-oxoheptanoic acid methyl ester 
• 205647-15-0 (3R)-[(tert-butyldimethylsilyl)oxy]-7-[4-(4-fluorophenyl)-2-isopropyl-5-methyl-1H-pyrrol-3-yl]-5-oxo-6-heptenoic acid methyl ester 
• 148966-79-4 (3R,5S)-7-[4-(4-fluorophenyl)-2-isopropyl-1-(methanesulfonyl)-5-methyl-1H-pyrrol-3-yl]-3,5-dihydroxy-6-heptenoic acid methyl ester 
• 188557-38-2 (E)-(R)-7-[4-(4-Fluoro-phenyl)-2-isopropyl-1-methanesulfonyl-5-methyl-1H-pyrrol-3-yl]-3-hydroxy-5-oxo-hept-6-enoic acid methyl ester 
• 160204-82-0 (3R)-[(tert-butyldimethylsilyl)oxy]-7-[4-(4-fluorophenyl)-2-isopropyl-1-(methanesulfonyl)-5-methyl-1H-pyrrol-3-yl]-5-oxo-6-heptenoic acid methyl ester 
• 87118-64-7 Monomethyl (3S)-(-)-3-hydroxypentanedioate 

Relevant articles and documents

Engineering of the Conformational Dynamics of Lipase to Increase Enantioselectivity

In order to increase the R-enantioselectivity of Candida antarctica lipase B (CALB) toward (R)-3-t-butyl-dimethyl-silyloxy glutaric acid methyl monoester at 30 °C, we engineered CALB conformational dynamics. Based on structural analysis and molecular dynamics simulations, two key residues (D223 and A281) were identified, and three mutants (D223V, A281S, and D223V/A281S) were designed to decrease the conformational dynamics of the pocket and channel. Computational and experimental evaluations were performed for all mutants, with the D223V/A281S mutant exhibiting high R-enantioselectivity (>99.00%; increased from 8.00%) and high space-time yield (107.54 g L-1 d-1 a 5.70-fold increase).

Synthesis of Novel HMG-CoA Reductase Inhibitors, I Naphthalene Analogs of Mevinolin

The title compounds 2 and their corresponding (6S) epimers 18 are prepared in several steps by starting with chiral formyl ester 5, and α-tetralones 10: (1) coupling reaction with the ylide generated from 11 to yield unsaturated ester 13, (2) reduction to the corresponding alcohol 14, (3) addition of the Grignard reagent derived from 14 to formyl ester 5 to afford the hydroxy esters 16 and 17, and (4) lactonization.This procedure is also used to synthesize the β-naphthyl analogs 29 and 30.Some results obtained from HMG-CoA reductase inhibitor screening are also reported. Key Words: HMG-CoA reductase inhibitors / Naphthylacetates / Pig liver esterase / Glutarate, 3-hydroxy / Lactones