13955-75-4

Upstream product

• 3689-69-8 (R)-6,10,14-trimethylpentadec-5-en-2-one 
• 59965-20-7 (R)-1-bromo-3,7-dimethyloctane 
• 1117-61-9 (3R)-citronellol 
• 85253-85-6 D-4,8-dimethyl-nonanenitrile 
• 13955-70-9 (R)-(-)-4,8-dimethylnonanoic dcid 
• 13853-24-2 (R)-3,7-dimethyl-octanoic acid methyl ester 
• 3796-69-8 (5Z,9Z)-6,10,14-trimethylpentadeca-5,9,13-trien-2-one 
• 87187-93-7 (3S,7S)-3,7,11-trimethyldodecan-1-ol 
• 1416127-55-3 (5Z,9Z)-6,10,14-trimethylpentadeca-5,9-dien-2-one 
• 3866-44-2 2-methyl-2-((3E,7E)-4,8,12-trimethyltrideca-3,7,11-trien-1-yl)-1,3-dioxolane 
• 1616077-91-8 2-methyl-2-((3E,7E)-4,8,12-trimethyltrideca-3,7-dien-1-yl)-1,3-dioxolane 
• 1117-52-8 6,10,14-trimethyl-5,9,13-pentadecatriene-2-on 
• 1616077-92-9 C₂₀H₄₀O₂ 
• 64611-89-8 6,10,14-trimethyl-5,9-pentadecadien-2-one 

Downstream Products

• 29171-23-1 3,7,11,15-tetramethyl-hexadec-1-yn-3-ol 
• 118100-85-9 trans-(RR/SS)-phytol 
• 118100-92-8 cis-(RR/SS)-phytol 

Relevant academic research and scientific papers

USING MIXTURES OF E/Z ISOMERS TO OBTAIN QUANTITATIVELY SPECIFIC PRODUCTS BY COMBINING ASYMMETRIC HYDROGENATION AND ISOMERIZATION

The present invention relates to a process of manufacturing compound having stereogenic centres from a mixture of E/Z isomers of unsaturated compounds having prochiral double bonds. The hydrogenation product has a specific desired configuration at the stereogenic centres. The process involves an asymmetric hydrogenation and an isomerization step. The process is very advantageous in that it forms the desired chiral product from a mixture of stereoisomers of the starting product in an efficient way.

(6R,10R)-6,10,14-TRIMETYLPENTADECAN-2-ONE PREPARED FROM 6,10,14-TRIMETYLPENTADECA-5,9,13-TRIEN-2-ONE OR 6,10,14-TRIMETYLPENTADECA-5,9-DIEN-2-ONE

The present invention relates to a process of manufacturing (6R,10R)- 6,10,14-trimetylpentadecan-2-one in a multistep synthesis from a mixture of (5E,9E)-, (5E,9Z)-, (5Z,9E)- and (5Z.9Z)- isomers of 6, 10, 14-trimetylpentadeca- 5,9,13-trien-2-one or 6,10,14-trimetylpentadeca-5,9-dien-2-one. The process is very advantageous in that it forms in an efficient way the desired chiral product from a mixture of stereoisomers of the starting product.

USING MIXTURES OF E/Z ISOMERS TO OBTAIN QUANTITATIVELY SPECIFIC PRODUCTS BY COMBINED ASYMMETRIC HYDROGENATIONS

The present invention relates to a process of manufacturing compound having stereogenic centres from a mixture of E/Z isomers of unsaturated compounds having prochiral double bonds. The hydrogenation product has a specific desired configuration at the stereogenic centres. The process involves two asymmetric hydrogenation steps. The process is very advantageous in that it forms the desired chiral product from a mixture of stereoisomers of the starting product in an efficient way.

PROCESS OF ASYMMETRIC HYDROGENATION OF KETALS AND ACETALS

The present invention relates to a process of the asymmetric hydrogenation of a ketal of an unsaturated ketone or an acetal of an unsaturated aldehyde by molecular hydrogen in the presence of at least one chiral iridium complex. This process yields chiral compounds in a very efficient way and is very advantageous in that the amount of iridium complex can be remarkably reduced.

Hydrogenation of ketones having at least a carbon-carbon double bond in the gamma-,delta-position

The present invention relates in a first aspect to a process for hydrogenation of ketones having at least a carbon-carbon double bond in the γ, δ-position to the keto group by hydrogen in the presence of at least one chiral iridium complex having a specific structure and particularly a specific aromatic ligand. It has been shown that this process leads to a strong increase in preferential formation of a single isomer. The process is particularly suitable for the hydrogenation of γ, δ -unsaturated ketones which can be used as flavours and fragrances or for the preparation of vitamin E and its derivatives or of flavours and fragrances.

A New Method for the Stereochemical Analysis of Acyclic Terpenoid Carbonyl Compounds

A new method for the determination of the enantiomeric and diastereoisomeric composition of terpenoid carbonyl compounds is presented.Separation of the diastereomeric (+)-L-diisopropyl-tartrate acetals derived from dihydrocitronellal (6), hexahydropseudoionone (3), hexahydrofarnesal (7), and hexahydrofarnesylacetone (4), the C10, C13, C15, and C18 intermediates in various syntheses of naturally occuring tocopherols and vitamin K1, can be achieved by capillary GC on a cyanopropylsilicon-coated glass column under standardized conditions.This technique, presenting a significant improvment over existing methodologies, is considered to be particularly useful for the analysis of highly enriched samples, typically obtained by present-day asymmetric synthesis.With reproducibilities of +/- 0.3 percent, and therefore, safe for routine analysis, the complete stereochemical characterization of terpenoids with 15 and 18 C-atoms bearing two stereogenic centres is performed in a single operation for the first time.