94844-37-8

Usage

Uses

Used in Pharmaceutical Industry:
(E)-4-[[(1,1-DiMethylethyl)diMethylsilyl]oxy]-2-butenoic Acid Ethyl Ester is used as a protected intermediate for the synthesis of 4-Amino-γ-butyrolactones, which are important building blocks in the development of pharmaceutical compounds. The asymmetrical synthesis of these lactones allows for the creation of enantiomerically pure products, which is crucial for the production of effective and safe drugs.
Used in Organic Synthesis:
In the field of organic synthesis, (E)-4-[[(1,1-DiMethylethyl)diMethylsilyl]oxy]-2-butenoic Acid Ethyl Ester serves as a versatile intermediate for the preparation of various organic compounds. Its unique structure allows for selective reactions and transformations, making it a valuable tool for chemists in designing and synthesizing complex molecules with specific properties and functions.

Upstream product

• 623-73-4 diazoacetic acid ethyl ester 
• 102191-92-4 tert-butyldimethylsiloxyacetaldehyde 
• 867-13-0 diethoxyphosphoryl-acetic acid ethyl ester 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 1099-45-2 ethyl (triphenylphosphoranylidene)acetate 
• 2459-05-4 (E)-4-ethoxy-4-oxobut-2-enoic acid 
• 10080-68-9 (E)-ethyl 4-hydroxybut-2-enoate 

Downstream Products

• 173423-74-0 (E)-4-(tert-Butyl-dimethyl-silanyloxy)-but-2-enoic acid 4-fluoro-phenyl ester 
• 944410-66-6 ethyl (3S,αR)-3-[N-benzyl-N-(α-methylbenzyl)-amino]-4-(tert-butyldimethylsilyloxy)butanoate 
• 1361293-78-8 1-(benzyloxycarbonyl)-6-((tert-butyldimethylsilyloxy)methyl)-4-(4-(2-(2,6-dichlorophenoxy)ethoxy)phenyl)-1,2,5,6-tetrahydropyridine-3-carboxylic acid 
• 1361293-77-7 1-(benzyloxycarbonyl)-2-((tert-butyldimethylsilyloxy)methyl)-4-(4-(2-(2,6-dichlorophenoxy)ethoxy)phenyl)-1,2,5,6-tetrahydropyridine-3-carboxylic acid 
• 1361293-70-0 1-benzyloxycarbonyl-6-((tert-butyldimethylsilyloxy)methyl)-4-(4-(2-(2-chlorophenoxy)ethoxy)phenyl)-1,2,5,6-tetrahydropyridine-3-carboxylic acid 
• 1361293-69-7 1-benzyloxycarbonyl-2-((tert-butyldimethylsilyloxy)methyl)-4-(4-(2-(2-chlorophenoxy)ethoxy)phenyl)-1,2,5,6-tetrahydropyridine-3-carboxylic acid 
• 1361293-65-3 1-benzyl 3-ethyl 6-((tert-butyldimethylsilyloxy)methyl)-4-(4-hydroxyphenyl)-5,6-dihydropyridine-1,3(2H)-dicarboxylate 
• 1361293-64-2 1-benzyl 3-ethyl 2-((tert-butyldimethylsilyloxy)methyl)-4-(4-hydroxyphenyl)-5,6-dihydropyridine-1,3(2H)-dicarboxylate 
• 1361293-75-5 1-Benzyl 3-ethyl 2-((tert-butyldimethylsilyloxy)methyl)-4-(4-(2-(2,6-dichlorophenoxy)ethoxy)phenyl)-5,6-dihydropyridine-1,3(2H)-dicarboxylate 
• 1361293-76-6 1-benzyl 3-ethyl 6-((tert-butyldimethylsilyloxy)methyl)-4-(4-(2-(2,6-dichlorophenoxy)ethoxy)phenyl)-5,6-dihydropyridine-1,3(2H)-dicarboxylate 
• 1361293-71-1 Benzyl 2-((tert-butyldimethylsilyloxy)methyl)-4-(4-(2-(2-chlorophenoxy)ethoxy)phenyl)-3-(cyclopropyl(2,3-dichlorobenzyl)carbamoyl)-5,6-dihydropyridine-1(2H)-carboxylate 

Relevant academic research and scientific papers

Structure revision of poecillastrin c and the absolute configuration of the β-hydroxyaspartic acid residue

The planar structure of poecillastrin C (1) was revised through selective reduction of the ester carbon. The absolute configuration of the β-hydroxyaspartic acid (OHAsp) residue was determined to be D-threo by Marfey's analysis. The acid hydrolysate of the reduction product of 1 liberated (2R, 3R)-2-amino-3, 4-dihydroxybutanoic acid, demonstrating that the β-carboxyl group in poecillastrin C was esterified. The structures of poecillastrins B-D and 73-deoxychondropsin A were also revised.

Formal syntheses of (?)-isoretronecanol, (+)-laburnine, and a concise enantioselective synthesis of (+)-turneforcidine

The synthesis of functionalized pyroglutamates 15 and 16 could be achieved by the application of recently developed diastereodivergent asymmetric Michael addition reaction of iminoglycinate 7 to ethyl γ-silyloxycrotonate with >98:2 diastereoselectivity followed by hydrolysis and lactamization. Formal syntheses of (?)-isoretronecanol and (+)-laburnine as well as a concise enantioselective synthesis of (+)-turneforcidine could be achieved from functionalized pyroglutamates 15 or 16.

Interrogating Pd(II) Anion Metathesis Using a Bifunctional Chemical Probe: A Transmetalation Switch

Ligand metathesis of Pd(II) complexes is mechanistically essential for cross-coupling. We present a study of halide→OH anion metathesis of (Ar)PdII complexes using vinylBPin as a bifunctional chemical probe with Pd(II)-dependent cross-coupling pathways. We identify the variables that profoundly impact this event and allow control to be leveraged. This then allows control of cross-coupling pathways via promotion or inhibition of organoboron transmetalation, leading to either Suzuki-Miyaura or Mizoroki-Heck products. We show how this transmetalation switch can be used to synthetic gain in a cascade cross-coupling/Diels-Alder reaction, delivering borylated or non-borylated carbocycles, including steroid-like scaffolds.

Syn-effect' in the diastereoselective alkylation of 3-[(E)-α,β-unsaturated-γ-substituted]-N-acyloxazolidinones

Synthetic methods for the formation of alkenes usually produce the E-alkene because it is more stable. However, in isomerization reaction (double bond migration) that takes place in α, β-unsaturated carbonyl compounds, when these carbonyl compounds are exposed to strong bases, furnish Z-alkenes highly stereoselective depending on the γ-substituent in the α, β-unsaturated carbonyl. This stereoselectivity can be attributed to the known Syn-effect. The synthetic value of this methodology is the achievement of chiral alcohol bearing an electron rich Z-alkene, as well as substituted, which was accomplished via removal of the oxazolidinone moiety under treatment with NaBH4, THF-H2O.

PYRROLOPYRIMIDINE AND PURINE DERIVATIVES

The present invention relates to compounds of formula (I) or pharmaceutically acceptable salts thereof, wherein Q, T, V, W, X, Y, Z, ring A, R1, R2, R3, R4, R5, R5a, R6, R7, R8, R9, R10, R11, R12, R13, R14, R15, R16, R17 and m are defined herein. There novel pyrrolopyrimidine and purine derivatives are useful in the treatment of abnormal cell growth, such as cancer, in mammals. Additional embodiments relate to pharmaceutical compositions containing the compounds and to methods of using the compounds and compositions in the treatment of abnormal cell growth in mammals.

Renin inhibitors

The invention relates to compounds having the formula: wherein the variables are as defined herein. The invention further relates to methods of making and using these compounds, and pharmaceutical compositions, kits and articles of manufacture comprise th

A concise diels-alder strategy for the asymmetric synthesis of (+)-albicanol, (+)-albicanyl acetate, (+)-dihydrodrimenin, and (-)-dihydroisodrimeninol

A short, mild, highly diastereo-, regio-, and stereoselective Diels-Alder strategy has been developed for the asymmetric synthesis of (+)albicanol, (+)-albicanyl acetate, (+)-dihydrodrimenin, and (-)-dihydroisodrimeninol.

Asymmetric synthesis of 4-amino-γ-butyrolactones via lithium amide conjugate addition

Upon treatment with homochiral lithium (R)-N-benzyl-N-(α-methylbenzyl)amide, γ-benzyloxy but-2-enoates undergo competitive conjugate addition and γ-deprotonation, while γ-tert-butyldimethylsilyloxy but-2-enoates undergo exclusive conjugate addition. Treatment of γ-benzyloxy or γ-tert-butyldimethylsilyloxy but-2-enamides with lithium (R)-N-benzyl-N-(α-methylbenzyl)amide furnishes exclusively the γ-benzyloxy- or γ-tert-butyldimethylsilyloxy-β-amino amide products of conjugate addition in high de. The γ-tert-butyldimethylsilyloxy-β-amino butanoate products of conjugate addition readily undergo O-desilylation and concomitant cyclisation to furnish 4-[N-benzyl-N-(α-methylbenzyl)amino]-γ-butyrolactone, which may be stereoselectively functionalised via deprotonation and alkylation?to give the corresponding trans-3-alkyl-4-amino-γ-butyrolactones. Alternatively, stereoselective alkylation of γ-benzyloxy- or γ-tert-butyldimethylsilyloxy-β-amino butanoates and butanamides through enolate formation and alkylation following a tandem (via the (Z)-lithium enolate) or stepwise (via the (E)-lithium enolate) protocol gives a range of separable syn- and anti-α-alkyl-β-amino esters and amides. O-Silyl deprotection of the syn- and anti-α-alkyl-β-amino butanoates with TBAF and concomitant cyclisation provide trans-3-alkyl-4-amino-γ-butyrolactones, consistent with epimerisation to the thermodynamically favoured trans-lactone occurring upon deprotection.

Synthesis of unsaturated esters from aldehydes: An inexpensive, practical alternative to the Horner-Emmons reaction under neutral conditions

A practical, efficient, and mild process is described for the synthesis of unsaturated esters from aldehydes in good yields and diastereoselectivities. All of the reagents used in the protocol are commercially available at a nominal price: N2CHCO2Et, catalytic (1 mol%) ReOCl3(PPh3)2, and (EtO)3P. Additionally, the reaction process can be carried out successfully in good yields (85%) and diastereoselectivities (>20:1) with reagent-grade solvent without prior purification of the reagents.

Synthesis of six-membered compounds by environmentally friendly cyclization using indirect electrolysis

[Ni(cyclam)](ClO4)2-catalyzed indirect electroreduction of olefinic bromides produced six-membered compounds in low to high yields. The synthetic intermediate 49 of Ipecac and Corynanthe alkaloids was obtained in 88% yield in a highly stereoselective manner. Lactam 66, the synthetic precursor of tacamonine, was prepared in 49% yield as a mixture of two diastereoisomers. The electrolysis of the bromoacetates gave the debrominated compounds in good yields.