147649-95-4

Upstream product

• 96930-18-6 (4R,5S)-4-methyl-3-pent-4-enoyl-5-phenyloxazolidin-2-one 
• 175272-36-3 (4R)-4-Benzyl-3-[(2S)-2-methyl-4-pentenoyl]-1,3-oxazolidin-2-one 
• 100-51-6 benzyl alcohol 
• 1233735-74-4 (S)-2-methyl-1-(1-phenyl-1H-imidazol-2-yl)pent-4-en-1-one 
• 1267597-50-1 (R)-4-isopropyl-3-((S)-2-methylpent-4-enoyl)-5,5-diphenyloxazolidin-2-one 
• 79563-29-4 (S)-4-isopropyl-3-((R)-2-methylpent-4-enoyl)oxazolidin-2-one 
• 153946-47-5 (4R,5S,2'S)-4-cyclohexyl-1,5-dimethyl-3-(2-methylpent-4-enoyl)imidazolidin-2-one 

Downstream Products

• 143225-28-9 benzyl (R)-2-methyl-4-pentenoate 
• 1357569-95-9 benzyl (2S)-4-acetoxy-5,5,5-trifluoro-2-methylpentanoate 
• 1357570-06-9 C₂₆H₃₆F₃N₃O₅ 
• 1357569-99-3 C₂₄H₃₂F₃N₃O₄ 
• 1357569-97-1 C₂₄H₃₂F₃N₃O₄ 
• 439217-35-3 (4S,6S)-2-Benzenesulfonyl-6-benzyloxy-1-{(2S,6S)-6-[(E)-5-(tert-butyl-diphenyl-silanyloxy)-pent-1-enyl]-2-methoxy-5,6-dihydro-2H-pyran-2-yl}-4-methyl-7-triethylsilanyloxy-heptan-3-ol 
• 439217-17-1 (4S,6S)-6-Benzyloxy-1-{(2S,6S)-6-[(E)-5-(tert-butyl-diphenyl-silanyloxy)-pent-1-enyl]-2-methoxy-5,6-dihydro-2H-pyran-2-yl}-4-methyl-7-triethylsilanyloxy-heptan-3-one 
• 439217-18-2 [(E)-5-((2S,6R,8R,11S,13S)-11-Benzyloxy-13-methyl-1,7,9-trioxa-dispiro[5.1.5.2]pentadec-4-en-2-yl)-pent-4-enyloxy]-tert-butyl-diphenyl-silane 
• 439217-19-3 [(E)-5-((2S,6R,8S,11S,13S)-11-Benzyloxy-13-methyl-1,7,9-trioxa-dispiro[5.1.5.2]pentadec-4-en-2-yl)-pent-4-enyloxy]-tert-butyl-diphenyl-silane 
• 439217-27-3 2,2-Dimethyl-propionic acid (2S,4S)-4-benzyloxy-2-methyl-5-triisopropylsilanyloxy-pentyl ester 
• 439217-28-4 2,2-Dimethyl-propionic acid (2S,4S)-4-benzyloxy-2-methyl-5-triethylsilanyloxy-pentyl ester 
• 439217-34-2 (2S,4S)-4-Benzyloxy-2-methyl-5-triethylsilanyloxy-pentan-1-ol 
• 439217-29-5 (2S,4S)-4-Benzyloxy-2-methyl-5-triethylsilanyloxy-pentanal 
• 439217-33-1 2,2-Dimethyl-propionic acid (2S,4S)-4-benzyloxy-5-hydroxy-2-methyl-pentyl ester 

Relevant academic research and scientific papers

Sensing remote chirality: Stereochemical determination of β-, γ-, and δ-chiral carboxylic acids

Determining the absolute stereochemisty of small molecules bearing remote nonfunctionalizable stereocenters is a challenging task. Presented is a solution in which appropriately substituted bis(porphyrin) tweezers are used. Complexation of a suitably derivatized β-, γ-, or δ-chiral carboxylic acid to the tweezer induces a predictable helicity of the bis(porphyrin), which is detected as a bisignate Cotton Effect (ECCD). The sign of the ECCD curve is correlated with the absolute stereochemistry of the substrate based on the derived working mnemonics in a predictable manner.

A peptide-embedded trifluoromethyl ketone catalyst for enantioselective epoxidation

The development of peptide-based oxidation catalysts that use a transiently generated dioxirane as the chemically active species is reported. The active catalyst is a chiral trifluoromethyl ketone (Tfk) with a pendant carboxylic acid that can be readily incorporated into a peptide. These peptides were capable of epoxidizing alkenes in high yield (up to 89%) and enantiomeric ratios (er) ranging from 69.0:31.0 to 91.0:9.0, depending on the alkene substitution pattern.

Palladium-catalyzed asymmetric allylic alkylation of 2-acylimidazoles as ester enolate equivalents

A broad range of highly enantioenriched 2-acylimidazoles are synthesized by palladium-catalyzed decarboxylative asymmetric allylic alkylation (DAAA) of 2-imidazolo-substituted enol carbonates. The enantioenriched 2-acylimidazole products can easily be converted to the corresponding carboxylic acid, ester, amide, and ketone derivatives with complete retention of the enantiopurity. The synthetic utility of this new method is demonstrated in the short, efficient synthesis of cetiedil.

Synthesis of the ABC ring system of Azaspiracid. 2. A systematic study into the effect of C(16) and C(17) substitution on bis-spirocyclization.

[reaction: see text] A systematic study into the effect of C(16) and C(17) substitution on the stereochemical outcome of bis-spirocyclization to form the ABC ring system of azaspiracid is disclosed. Successful construction of the natural 10R,13R bis-spirocyclic stereochemistry has been accomplished on the C(16) benzyloxy-containing precursor.

Applications of crotyldiisopinocampheylboranes in synthesis: A formal total synthesis of (+)-calyculin A

The formal total synthesis of the marine metabolite (+)-calyculin A is reported. The key steps involve (i) the use of Brown allylboration chemistry to control the relative and absolute stereochemistry of homoallylic alcohol arrays, thus setting eight of the desired stereocenters; (ii) Stille coupling methodology in the construction of the cyano tetraene unit of the natural product; and (iii) a modified Cornforth-Meyers approach to the synthesis of the oxazole fragment.

SUBSTITUTED OXOTREMORINE DERIVATIVES

This disclosure describes novel substituted oxotremorine derivatives of formula I having nitrogen, oxygen or sulfur groups and the prodrug forms of these derivatives. The compounds have cholinergic activity. Also disclosed are methods for treating diseases of the central nervous system in mammals employing the compounds, pharmaceutical preparations containing the compounds and the processes for the production of the compounds. STR1

Substituted oxotremorine derivatives and pharmaceutical use thereof

This disclosure describes novel substituted oxotremorine derivatives of formula I having nitrogen, oxygen or sulfur groups and the prodrug forms of these derivatives. The compounds have cholinergic activity. Also disclosed are methods for treating disease

Ephedrine-Derived Imidazolidin-2-ones. Broad Utility Chiral Auxiliaries in Asymmetric Synthesis

The scope of the readily available (4R,5S)-1,5-dimethyl-4-phenylimidazolidin-2-one (4) and its 4-cyclohexyl analogue 6 as practical, efficient chiral auxiliaries has been demonstrated.The enolate chemistry of their N-acyl derivatives exhibits features which recommend their use in asymmetric synthesis.The stereoselective boron-mediated aldol as well as alkylation and acylation results are presented.The steric control benefit derived by conversion of phenyl to cyclohexyl is highlighted. - Key Words: Imidazolidin-2-one, (4R,5S)-1,5-dimethyl-5-phenyl- or cyclohexyl- / (-)-Ephedrine / Stereoselective aldol / alkylation, acylation