130796-32-6

Upstream product

• 133521-66-1 (4S,5R)-Ethyl 2,2-dimethyl-5-phenyl-1,3-dioxolane-4-carboxylate 
• 133520-57-7 (4S,5R)-4-(hydroxymethyl)-2,2-dimethyl-5-phenyl-1,3-dioxolane 
• 20698-91-3 (R)-methyl mandelate 
• 343953-79-7 2,2-Dimethyl-5-phenyl-[1,3]dioxolane-4-carbonitrile 
• 4192-77-2 ethyl cinnamate 
• 130718-66-0 (R)-3-phenyl-1,1-bis(p-tolylthio)-3-(trimethylsilyloxy)propan-2-one 
• 130718-75-1 (4R,5R)-cis-4--2,2-dimethyl-5-phenyl-1,3-dioxolan 
• 130718-68-2 (R)-3-hydroxy-3-phenyl-1,1-bis(p-tolylthio)propan-2-one 
• 109459-35-0 methyl (R)-2-phenyl-2-((trimethylsilyl)oxy)acetate 
• 133421-01-9 3-(Dimethylthexylsiloxy)-3-phenyl-2-(trimethylsiloxy)propannitril 
• 5695-95-4 (R)-2,3-Dihydroxy-3-phenyl-propionic acid 
• 56503-11-8 ethyl (3R)-2,3-dihydroxy-3-phenylpropanoate 
• 103-26-4 methyl cinnamate 
• 103-26-4 Methyl cinnamate 

Downstream Products

• 133421-03-1 [1-((4R,5R)-2,2-Dimethyl-5-phenyl-[1,3]dioxolan-4-yl)-meth-(Z)-ylidene]-((R)-2-methoxymethyl-pyrrolidin-1-yl)-amine 
• 130796-35-9 (4S,5R)-trans-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-carboxylic acid 
• 79224-61-6 2,3-O-Isopropyliden-3-phenylglycerinaldehydcyanydrin 

Relevant academic research and scientific papers

Asymmetric Total Syntheses of Aetheramides and Their Stereoisomers: Stereochemical Assignment of Aetheramides

The concise total syntheses of the potent HIV inhibitors aetheramides A and B (IC50 values of 15 and 18 nM), as well as three pairs of their stereoisomers, were achieved, which allowed the complete stereochemical assignment of aetheramides for the first time. With a longest linear sequence of 15 steps, the convergent, fully stereocontrolled route provided aetheramides A and B in 5.3% and 3.6% yields, respectively. The synthetic strategy features efficient Stille coupling for macrocyclization, asymmetric aldol reactions to establish the ambiguous stereochemistries at C-17 and C-26, and implementation of mild conditions to avoid the epimerization of the sensitive polyketide moiety and the migration of the labile lactone.

Highly diastereoselective total syntheses of (+)-7-epigoniodiol, (-)-8-epigoniodiol, and (+)-9-deoxygoniopypyrone

An expedient concise total synthesis of (+)-7-epigoniodiol, (-)-8-epigoniodiol, and (+)-9-deoxygoniopypyrone is accomplished. The key transformations include a catalytic hydroxylation and base-mediated N-(acetyl)oxazolidinone addition reactions, which cou

Oxidative cyclization of γ-alkylidene butenolides. Stereoselective preparation of spirolactones

A new route to 1,6-dioxaspiro[4.4]non-3-en-2-ones is established by bromoetherification of dihydroxybutenolides. An asymmetric total synthesis of 8-epi-crassalactone D starting from methyl cinnamate has been accomplished. ARKAT-USA, Inc.

Structure-activity relationship (SAR) studies of 3-(2-amino-ethyl)-5-(4-ethoxy-benzylidene)-thiazolidine-2,4-dione: Development of potential substrate-specific ERK1/2 inhibitors

A series of analogs of 3-(2-amino-ethyl)-5-(4-ethoxy-benzylidene)-thiazolidine-2,4-dione, a putative substrate-specific ERK1/2 inhibitor, were synthesized and biologically characterized in human leukemia U937 cells to define its pharmacophore. It was disc

Stereocontrolled synthesis of gem-difluoromethylenated goniodiols and goniothalamin epoxides based on ring-closing metathesis

An efficient and general method to stereoselectively synthesize gem-difluoromethylenated goniodiols and goniothalamin epoxides has been developed. The introduction of a gem-difluoromethyl-containing group was achieved by the reaction of aldehydes with 3-bromo-3,3-difluoropropene in the presence of indium. The gem-difluoromethylenated α,β-unsaturated- δ-lactone moiety was constructed through the ring-closing metathesis of highly electron-deficient gew-difluoromethylenated acryloyl esters by Grubbs' II catalyst in toluene at reflux. Georg Thieme Verlag Stuttgart.

On the selectivity of oxynitrilases towards α-oxygenated aldehydes

Different α-alkoxy and α,β-di-alkoxy substituted aldehydes have been submitted to the catalytic action of the oxynitrilases from almond (PaHNL) or from Hevea brasiliensis (HbHNL), in order to explore the possibility of using these enzymes for the preparation of complex cyanohydrins. The selectivity of both enzymes towards these compounds was found to be largely dependent on the substitutents, being low with the aldehydes carrying the sterically more demanding phenyl substituent. Contrary to the chemical addition of HCN, which always occurs with a slight preference for the formation of the anti diastereoisomers, the enzymatic cyanuration - occurring with a facial preference, Si or Re according to the biocatalyst used - gave a mixture of cyanohydrins that, depending on the starting enantiomeric aldehyde, can be enriched in the syn diastereoisomers.

Synthesis of O-Protected (R)-2-Hydroxy Aldehyde and Their Hydrocyanation

The synthesis of O-silyl- and O-benzyl-protected (R)-2-hydroxy aldehydes (R)-6 from (R)-2-hydroxy carboxylic acids (R)-1 is described.While attempts for their diastereoselective hydrocyanation with hydrocyanic acid and (R)-oxynitrilase as catalyst have not been successful, the cyano silylation with trimethylsilyl cyanide occurred diastereoselectively with a ratio of 81:19 preferring the threo form without racemization at C-2 of the 2-hydroxy aldehyde. Key Words : (R)-2-Hydroxy aldehydes, O-protected / Hydrocyanation

Synthesis of Aryl Carbohydrate Synthons and 2,3-Dihydroxypropanoic Acid Derivatives of High Optical Purity

General routes to bith L and D aryl carbohydrate precursors and to erythro and threo 2,3-dihydroxypropanoic acid of high optical purity have been established from readily available optically active aryl cyanohydrins.