77924-28-8

Usage

Uses

Used in Pharmaceutical Industry:
1-Ethyl 4-(tert-Butyl) 2-(diethyl phosphono)succinate is used as a key intermediate in the synthesis of Dalesconols A and B, which are potent immunosuppressant agents. These agents are valuable in the development of immunosuppressive therapies for the treatment of autoimmune diseases and transplantation.
In the synthesis of Dalesconols A and B, 1-Ethyl 4-(tert-Butyl) 2-(diethyl phosphono)succinate plays a crucial role in the formation of the desired molecular structures, enabling the production of these effective immunosuppressants. Its unique properties and reactivity make it an indispensable component in the development of these pharmaceutical agents.

Upstream product

• 867-13-0 diethoxyphosphoryl-acetic acid ethyl ester 
• 5292-43-3 bromoacetic acid tert-butyl ester 

Downstream Products

• 157188-11-9 2-[1-(4-Fluoro-phenyl)-meth-(E)-ylidene]-succinic acid 4-tert-butyl ester 1-ethyl ester 
• 1031223-86-5 2-[1-Phenyl-meth-(E)-ylidene]-succinic acid 4-tert-butyl ester 1-ethyl ester 
• 157188-05-1 2-[1-(4-Methoxy-phenyl)-meth-(E)-ylidene]-succinic acid 4-tert-butyl ester 1-ethyl ester 
• 157188-03-9 2-[1-(2-Methoxy-phenyl)-meth-(E)-ylidene]-succinic acid 4-tert-butyl ester 1-ethyl ester 
• 162147-22-0 tert-Butyl (E)-4-(2'-bromo-5'-isopropoxyphenyl)-3-ethoxycarbonyl-3-butenoate 
• 157188-08-4 tert-butyl (E)-3-(ethoxycarbonyl)-4-(4-nitrophenyl)-3-butenoate 
• 477849-68-6 2-[1-(2,4-Dimethoxy-phenyl)-meth-(E)-ylidene]-succinic acid 4-tert-butyl ester 1-ethyl ester 
• 693784-39-3 2-[1-(5-Benzyloxy-2,3-dimethoxy-phenyl)-meth-(E)-ylidene]-succinic acid 1-ethyl ester 
• 676601-32-4 4-t-butyl 1-ethyl 2-(diethoxyphosphoryl)-2-(phenylseleno)butanedioate 
• 676601-34-6 (E)-2-(Diethoxy-phosphoryl)-but-2-enedioic acid 1-ethyl ester 4-(3-phenyl-prop-2-ynyl) ester 
• 676601-35-7 (E)-2-(Diethoxy-phosphoryl)-3-[methyl-(3-phenyl-prop-2-ynyl)-carbamoyl]-acrylic acid ethyl ester 
• 116129-86-3 (E)-4-phenyl-3-carbethoxyethylbut-3-enoic acid 

Relevant academic research and scientific papers

Model study toward total synthesis of dimeric pyranonaphthoquinones: Synthesis of hemi-actinorhodin#

In connection with our synthetic study toward the dimeric pyranonaphthoquinone antibiotics, actinorhodin (1) and β-naphthocyclinone (3), we describe herein the synthesis of a monomer, hemi-actinorhodin (6) as a model target. Several implications were gained, including (1) stereoselective synthesis of the pyranonaphthoquinone, (2) viable construction of the naphthazarin core, and (3) the final deprotection conditions.

Atroposelective Total Synthesis of the Fourfold ortho-Substituted Naphthyltetrahydroisoquinoline Biaryl O,N-Dimethylhamatine

A stereoselective total synthesis of O,N-dimethylhamatine, an analogue of an axially chiral naphthylisoquinoline natural biaryl product from tropical Ancistrocladus lianas, is reported. The route features a late-stage atropo-diastereoselective biaryl bond

Total Synthesis of Eleuthoside A; Application of Rh-Catalyzed Intramolecular Cyclization of Diazonaphthoquinone

The first total synthesis of (±)-eleutherol and eleuthoside A, the natural cytotoxic substances extracted from medicinal Indonesian plant, is described. First, the synthesis of (±)-eleutherol has been accomplished in nine steps starting from bromo methoxy aldehyde with the aid of diazo-transfer chemistry approach. Second, a metal-catalyzed intramolecular cyclization reaction of the corresponding diazonaphthoquinone led to the desired eleuotherol, which served as a precursor to eleuthoside A. Then, several glycosidation routes, using different glucosyl donors, were experimented to reach effective O-glycosidation of eleutherol. The only successful strategy involved Koenigs-Knorr glycosidation using peracetyl glycosyl bromide in the presence of Ag 2 O and quinoline. This strategy furnished our desired acetylated glycoside of β-configuration, regioselectively. Finally, deacetylation and successive separation of diastereomers were conducted to give eleuthoside A.

SYNTHESIS OF THE POTENT IMMUNOSUPPRESSANT AGENTS DALESCONOL A AND B

This invention relates to compounds having the structure: wherein bonds α, β, γ, δ, ω, η, χ, ε, κ, and μ are each present or absent, and R1-R18 are various substituents described herein.

Total syntheses of dalesconol A and B

(Chemical equation Presented) (Chemical equation Presented) A polycyclic collapse: Use of a carefully designed acyclic intermediate participated in a cascade reaction that formed the entire core of the polyketide-derived dalesconols in a single flask (see scheme). A number of additional and carefully controlled synthetic operations completed an expeditious synthesis of both of these highly bioactive natural products as well as structural congenors.

Lewis acid-promoted cyclization of heteroatom-substituted enynes.

Lewis acid-promoted cyclizations of heteroatom-substituted enynes have been examined. The reaction of enynes and bearing silicon substituents on an alkyne afforded the halogenated five-membered gamma-lactones and gamma-lactams as the main products. The reaction of substrates and having 2-phosphonoacrylate instead of malonate also gave halogenated five-membered cyclic compounds and as the major products. The cyclized products are highly substituted and potentially useful for further synthetic transformations.

Asymmetric synthesis of an MMP-3 inhibitor incorporating a 2-alkyl succinate motif

An efficient and practical synthesis is presented of the pharmaceutically active MMP-3 inhibitor UK-370,106 (1) via an olefination/catalytic asymmetric hydrogenation sequence. Commercially available 5-bromo-2-iodotoluene was converted in two steps to the

A new synthesis of Rhein

A novel synthesis of Rhein (2), the active metabolite of the anti-osteoarthritic drug Diacetyl Rhein (1) has been achieved. Key steps include stereospecific olefination of aldehyde 21 with novel phosphonate 28 and the cylisation of acid 31 to produce anthracene 32.

tert-Butyl-3-carboxyethyl-3-phosphonodiethylpropionate. A novel reagent for Stobbe-like condensations

tert-Butyl-3-carboxyethyl-3-phosphonodiethylpropionate was prepared and reacted with a range of aldehydes to give, after hydrolysis, itaconic half esters.

A general approach to substituted itaconate esters

A general approach to the synthesis of various itaconates including 3-substituted esters is presented. The complementarity of the approach is also shown.