109744-49-2

Usage

Uses

Used in Organic Synthesis:
(3R)-3-(tert-Butyldimethylsilyl)oxypentanedioate-1-methyl monoester is used as a protecting group in organic synthesis for the purpose of shielding functional groups during chemical reactions, allowing for selective reactions to occur at other sites on the molecule.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, (3R)-3-(tert-Butyldimethylsilyl)oxypentanedioate-1-methyl monoester may be employed as an intermediate in the synthesis of complex organic molecules, including potential drug candidates, due to its ability to protect and manipulate functional groups during the synthesis process.
Used in Chemical Research:
(3R)-3-(tert-Butyldimethylsilyl)oxypentanedioate-1-methyl monoester is used as a research tool in chemical laboratories for studying the reactivity and properties of complex organic compounds, contributing to the advancement of synthetic methodologies and the development of new chemical reactions.

InChI:InChI=1/C12H24O5Si/c1-12(2,3)18(5,6)17-9(7-10(13)14)8-11(15)16-4/h9H,7-8H2,1-6H3,(H,13,14)/t9-/m1/s1

Upstream product

• 96555-56-5 (3S,1'S)-methyl 1'-phenylethyl 3-<(tert-butyldimethylsilyl)oxy>pentanedioate 
• 124-41-4 sodium methylate 
• 131466-61-0 (3R)-3-<(tert-Butyldimethylsilyl)oxy>pentanedioic acid 1-<(R)-mandelic acid> ester 
• 121980-45-8 (3R)-(-)-methyl 3-<(tert-butyldimethylsilyl)oxy>-4-formylbutanoate 
• 140164-51-8 methyl 2-((4R,6S)-6-(hydroxymethyl)-2,2-dimethyl-1,3-dioxane-4-yl)acetate 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 91424-39-4 3-[[(1,1-Dimethylethyl)dimethylsilyl]-oxy]pentanedioic acid,diethyl ester 
• 32328-03-3 diethyl 3-hydroxyglutarate 
• 67-56-1 methanol 
• 91424-40-7 3-(tert-butyldimethylsilyloxy)glutaric anhydride 
• 1350364-00-9 hydrogen (3R)-1-methyl 3-[(tert-butyldimethylsilyl)-oxy]pentanedioate cyclohexylamine salt 
• 7250-55-7 dimethyl 3-hydroxypentanedioate 
• 90613-44-8 methyl 3-acetoxypentanedioate 

Downstream Products

• 1350364-18-9 C₁₅H₂₈O₇Si 
• 1350364-05-4 hydrogen (3R)-1-methyl 3-[(tert-butyldimethylsilyl)-oxy]pentanedioate benzylamine salt 
• 1350364-00-9 hydrogen (3R)-1-methyl 3-[(tert-butyldimethylsilyl)-oxy]pentanedioate cyclohexylamine salt 
• 147118-35-2 methyl (3R)-3-(tert-butyldimethylsilyloxy)-5-oxo-6-triphenylphosphoranylidenehexanoate 
• 147118-39-6 methyl (3R,6E)-7-[4-(4-fluorophenyl)-2-(N-methylmethanesulfonamido)-6-(propan-2-yl)pyrimidin-5-yl]-3-hydroxy-5-oxohept-6-enoate 
• 182075-76-9 (R,E)-methyl 3-(tert-butyldimethylsilyloxy)-7-(2-cyclopropyl-4-(-4-fluorophenyl)-quinolin-3-yl)-5-oxohept-6-enoate 
• 917752-45-5 methyl (E)-7-[2-cyclopropyl-4-(4-flurophenyl)-3-quinolinyl]-3-hydroxy-5-oxo-6-heptenate 
• 1622873-98-6 C₃₂H₄₈FN₃O₆SSi 

Relevant academic research and scientific papers

Preparation method of high-purity statin drug intermediate

The invention relates to a preparation method of a high-purity statin drug intermediate. The preparation method is characterized in that 3-hydroxyl ethyl glutarate is used as the initial raw material to prepare (3R)-tert-butyl dimethyl silyloxy-5-oxo-6-triphenyl phosphine caproate (abbreviated as J6) through substitution reaction, hydrolysis reaction, cyclization reaction, resolution reaction, hydrogenation reaction, acylation reaction and Wittig reaction. The preparation method is mild in condition, stable in process, cheap in raw material, easy in raw material obtaining, easy in three-waste treatment, low in preparation cost, high in product purity and suitable for industrial production.

A synthetic method of the compound

The invention relates to the field of chemistry and in particular relates to the field of medical chemistry. The invention aims to find a novel synthetic route suitable for Vb compounds in industrial production and adaptively provides a specific implementation process of the novel synthetic route, so that high-purity low-cost Vb compounds can be obtained. The compound Vb is prepared by taking a compound I as an initial raw material, so that the traditional Vb synthetic process is replaced. With the adoption of the synthetic route disclosed by the invention, the invention has the advantages that 1, dangerous and expensive butyl lithium is not used; 2, hydrogenation is avoided, and expensive metal palladium is avoided; and 3, more important, debenzylation byproducts in the hydrogenation are avoided. Meanwhile, because the price of the compound I is low, after the synthetic route disclosed by the invention is adopted, the industrial production need of the obtained high-purity low-cost compound V can be met.

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).

Green synthesis of (R)-3-TBDMSO glutaric acid methyl monoester using Novozym 435 in non-aqueous media

An efficient biocatalytic synthesis of (R)-3-TBDMSO glutaric acid methyl monoester (R-J6), an important intermediate in the synthesis of rosuvastatin, has been developed using a green catalytic route in the presence of lipase, conducted under mild conditions without additional chiral reagents. Enzyme screening indicated Novozym 435 to be the most efficient biocatalyst for R-J6 synthesis. Methanol, which was the most effective alcohol for synthesis of R-monoester, was identified as the best acyl acceptor by molecular docking. The optimal conditions for synthesis of R-J6 were as follows: 50 g L-1 catalyst, 3 sp;:sp;1 molar ratio of methanol sp;:sp;substrate, 200 g L-1 substrate, iso-octane as solvent, orbital shaking at 200 rpm, and an incubation time of 24 h at 35°C. The key factor affecting the yield of R-J6 was the molar ratio of methanol to substrate found by an orthogonal array experimental design. Consequently, the desired product, R-J6, was afforded with a titer of 117.2 g L-1, a yield of 58.6%, and productivity of 4.88 g L-1 h-1. This green method holds promise for the preparation of kilogram quantities of (R)-3-substituted glutaric acid monoesters.

AN IMPROVED PROCESS FOR THE PREPARATION OF AN INTERMEDIATE OF HMG-COA REDUCTASE INHIBITORS

The present invention relates to an improved process for the preparation of intermediates of HMG-CoA reductase inhibitors of Formulae-IXa or IXb and further conversion to HMG-CoA reductase inhibitors and pharmaceutically acceptable salts thereof.

CINCHONA-BASED BIFUNCTIONAL ORGANOCATALYSTS AND METHOD FOR PREPARING CHIRAL HEMIESTERS USING THE SAME

The present invention relates to cinchona-based bifunctional organocatalysts and methods for preparing chiral hemiesters using the same. More specifically, the present invention relates to methods for preparing chiral hemiesters from prochiral or meso cyclic acid anhydrides via desymmetrization, using bifunctional cinchona alkaloid catalysts comprising sulfonamide functional groups.

Enantioselective alcoholysis of meso-glutaric anhydrides catalyzed by Cinchona-based sulfonamide catalysts

The bifunctional Cinchona-based sulfonamide catalysts showed the highest levels of enantioselectivity reported to date in the alcoholytic desymmetrization of meioglutaric anhydrides. Density functional theory (DFT) computational studies provide detailed insight into the observed sense of enantioselectivity. Moreover, detailed experimental studies and single crystal X-ray analysis confirmed that these bifunctional organocatalysts 3 do not form Hbonded self-aggregates in both solution and solid state. The synthetic utility of this methodology was also demonstrated in the synthesis of pharmaceutically important γ-amino acids, such as (S)-pregabalin. Of the many asymmetric syntheses of enantiomerically pure (S)-pregabalin reported to date, our synthesis requires the least number of and the simplest steps.

A PROCESS FOR THE PREPARATION OF ROSUVASTATIN INVOLVING A TEMPO-MEDIATED OXIDATION STEP

The present invention provides a process for the preparation of the rosuvastatin intermediate FPP-CHO and its conversion to rosuvastatin and pharmaceutically acceptable salts thereof.

Practical synthesis of chiral synthons for the preparation of HMG-CoA reductase inhibitors

A practical procedure for the enantioselective preparation of optically pure (R)- and (S)-monomethyl esters of 3-[(tert-butyldimethylsilyl)oxy]pentanedioic acid has been developed by diastereoselective ring-opening of 3-[(tert-butyldimethylsilyl)oxy]pentanedioic anhydride 5 by benzyl (R)- and (S)-mandelate, respectively. These half-esters afforded chiral Wittig reagent 2 and Horner-Wadsworth-Emmons (HWE) reagent 1 efficiently which have been proved to be useful in the synthesis of HMG-CoA reductase inhibitors. The method is applied to the synthesis of the (R)-3-methylglutaric acid, monomethyl ester.

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