20013-34-7

Upstream product

• 6802-75-1 diethyl isopropylidenemalonate 
• 3917-41-7 (2E,4E)-3-methyl-5-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4-pentadienal 
• 113089-08-0 ethyl 14-carboxyretinoate 
• 259181-78-7 2-[(2E,4E,6E)-1,5-Dimethyl-7-(2,6,6-trimethyl-cyclohex-1-enyl)-hepta-2,4,6-trien-(E)-ylidene]-malonic acid monomethyl ester 
• 777916-02-6 2-[(4E,6E)-3-Benzenesulfonyl-1,5-dimethyl-7-(2,6,6-trimethyl-cyclohex-1-enyl)-hepta-4,6-dienylidene]-malonic acid diethyl ester 
• 13830-91-6 diethyl bromoisopropylidenemalonate 
• 38987-91-6 5-(2,6,6-trimethyl-cyclohex-1-enyl)-3-methyl-1-phenyl-sulphonyl-penta-2,4-diene 
• 22035-53-6 dimethyl isopropylidenemalonate 
• 85458-25-9 5,5-dimethoxy-1-(2,6,6-trimethyl-cyclohex-1-enyl)-pent-1-en-3-one 
• 180736-79-2 2-[3-(2,2-dimethoxy-ethyl)-buta-1,3-dienyl]-1,3,3-trimethylcyclohexene 
• 180736-80-5 (4E)-3-methylene-5-(2,6,6-trimethyl-1-cyclohexen-1-yl)-4-pentenal 

Downstream Products

• 4759-48-2 13-cis-retinoic acid 
• 302-79-4 all-trans-retinoic-acid 
• 70244-78-9 2-((1E,3E,5E)-3,7-dimethylocta-1,3,5,7-tetraen-1-yl)-1,3,3-trimethylcyclohex-1-ene 

Relevant academic research and scientific papers

Structure-activity relationships of methylene or terminal side chain modified retinoids on the differentiation and cell death signaling in NB4 promyelocytic leukemia cells

New structure-activity relationships of a series of methylene or side chain modified retinoids on NB4 acute promyelocytic leukemia cells are investigated. The differentiation- and apoptosis-inducing potential of these compounds is analyzed on the basis of

A survey of mono- or bis-decarboxylation of β-methyl polyethylenic-malonic acids

Diverse experimental conditions, leading to mono- or bis-decarboxylation of β-methyl polyethylenic-malonic acids, were examined. A clean and easy bis-decarboxylation was reported.

Stereoselective and convergent syntheses of retinoic acid and its ester derivatives by the sulfone olefination reaction

An extensive study on the stereoselective and convergent syntheses of retinoic acid and its ester derivatives utilizing the Julia sulfone olefination reaction has been reported. Various C5 units of the acid 4a, the esters 4b-e from the chemically and biologically important alcohols, and the furanone 6 have been prepared and coupled with the C15 allylic sulfone 3 to give the C20 compounds 10 and 11, which provided all-(E)-retinoic acid (1a), its ester derivatives 1b-e, and the furanone analogue 12b in a highly stereoselective manner after dehydrosulfonation reaction. The Julia olefination reaction of the C5 diester 13 and the C15 allylic sulfone 3 produced the known C20 diacid 15 which underwent stereoselective mono-decarboxylation to provide either 13-(Z)-retinoic acid (2) or all-(E)-retinoic acid (1) depending on the reagent used.

Stereoselective syntheses of 13E and 13Z retinoic acids via a new intermediate C-15 β-methylenealdehyde

The methylene-de-oxo-bisubstitution reaction between dimethyl isopropylidene malonate and the C-15 β-methylenealdehyde 1 which could serve as substitute for E β-ionylideneacetaldehyde 2, produces stereoselectively the E,E olefin. Hence, new stereoselective syntheses of 13 E and 13 Z retinoic acids were described. (C) 2000 Elsevier Science Ltd.

Stereoselective synthesis of 13Z retinoic acids via β-methylenealdehydes as synthons

A stereoselective synthesis of 13Z retinoic acids via β-methylenealdehydes is described. In methylene-de-oxo-bisubstitution reactions (Knoevenagel, Stobbe, etc.), these new synthons produce stereoselectively E olefins. Hence, a synthesis of 13Z retinoic acids is described, via a stereospecific monodecarboxylation of carboxy-14-retinoic acids.

Terminal Bifunctional Retinoids. Synthesis and Evaluation Related to Cancer Chemopreventive Activity

Retinoids that have two functional groups at the side-chain terminus have been synthesized.The two terminal functional groups are combinations of the carboxyl, carbethoxy, and N-(ethylamino)carbonyl groups.The synthesis route is based on the sodium amide