62472-76-8

Upstream product

• 822-02-6 5-undecynoic acid 
• 75415-21-3 ethyl (Z)-undec-5-enoate 
• 26001-58-1 (Z)-oct-2-en-1-ol 
• 54471-23-7 methyl 5-(Z)-undecenoate 
• 74198-04-2 (5Z)-5-undecenonitrile 
• 57074-37-0 (Z)-4-decen-1-ol 
• 86301-89-5 (Z)-dec-4-enyl methanesulfonate 
• 66-25-1 hexanal 
• 17373-89-6 2-hexylidenecyclopentanone 
• 111-66-0 oct-1-ene 
• 6026-86-4 methyl 4-formylbutanoate 
• 54299-12-6 1-cyanodec-4-yne 
• 628-71-7 1-Heptyne 
• 4762-26-9 hexyltriphenylphosphonium bromide 

Downstream Products

• 54844-65-4 (Z)-6-heneicosen-11-one 

Relevant academic research and scientific papers

CATIONIC LIPIDS FOR LIPID NANOPARTICLE DELIVERY OF THERAPEUTICS TO HEPATIC STELLATE CELLS

Certain embodiments of the invention provide lipids useful for preparing lipid nanoparticles for delivering therapeutic agents to, e.g., hepatic stellate cells.

Development of small-molecule inhibitors of fatty acyl-AMP and fatty acyl-CoA ligases in Mycobacterium tuberculosis

Lipid metabolism in Mycobacterium tuberculosis (Mtb) relies on 34 fatty acid adenylating enzymes (FadDs) that can be grouped into two classes: fatty acyl-CoA ligases (FACLs) involved in lipid and cholesterol catabolism and long chain fatty acyl-AMP ligases (FAALs) involved in biosynthesis of the numerous essential and virulence-conferring lipids found in Mtb. The precise biochemical roles of many FACLs remain poorly characterized while the functionally non-redundant FAALs are much better understood. Here we describe the systematic investigation of 5′-O-[N-(alkanoyl)sulfamoyl]adenosine (alkanoyl adenosine monosulfamate, alkanoyl-AMS) analogs as potential multitarget FadD inhibitors for their antitubercular activity and biochemical selectivity towards representative FAAL and FACL enzymes. We identified several potent compounds including 12-azidododecanoyl-AMS 28, 11-phenoxyundecanoyl-AMS 32, and nonyloxyacetyl-AMS 36 with minimum inhibitory concentrations (MICs) against M. tuberculosis ranging from 0.098 to 3.13 μM. Compound 32 was notable for its impressive biochemical selectivity against FAAL28 (apparent Ki = 0.7 μM) versus FACL19 (Ki > 100 μM), and uniform activity against a panel of multidrug and extensively drug-resistant TB strains with MICs ranging from 3.13 to 12.5 μM in minimal (GAST) and rich (7H9) media. The SAR analysis provided valuable insights for further optimization of 32 and also identified limitations to overcome.

Preparation of stereochemically pure E- and Z-alkenoic acids and their methyl esters from bicyclo[n.1.0]alkan-1-ols. Application in the synthesis of insect pheromones

Oxidative cleavage of exo- and endo-alkyl- and hydroxyalkyl-substituted bicyclo[n.1.0]alkan-1-ols with (diacetoxy-λ3-iodanyl)benzene gave the corresponding methyl alkenoates exclusively with E or Z configuration of the double bond. This reaction was used as the key stage in the syntheses of stereoisomerically pure components of pest insect pheromones: (E)-dodec-9-en-1-yl acetate (European pine shoot moth Rhyacionia buoliana), (Z)-tetradec-11-en-1-yl acetate (European oak leafroller Tortrix viridana), and (3E,8Z,11Z)-tetradeca-3,8,11-trien-1-yl acetate (tomato leafminer Tuta absoluta).

Ultrasound mediated synthesis of a few naturally occurring compounds

Synthesis of 2-methylheptadecane 1, 14-methylpentadecan-3-one 2, 6-oxo-1-nonanol 3, 5-(Z)-undecenoic acid 4 and 2-tridecanone 5 have been accomplished utilizing zinc-copper couple catalyzed conjugate addition of α,β-unsaturated carbonyl compounds under aqueous sonochemical conditions as the key step.

New Synthetic Methods, 12. - The Stereoselectivity of the Ramberg-Baecklund Rearrangement

The influence of strong and weak bases in different solvents on the (E)/(Z) ratio of the Ramberg-Baecklund olefin synthesis of α-halosulfoncarboxylic acids in studied.With potassium tert-butoxide in dry dimethyl sulfoxide (E) ratios of more than 97 percent are achieved.With weak bases, such as 0.25 N sodium hydroxide, we found only equal amounts of (E) and (Z) olefins, apart from a few exceptions.

Z/E-Isomerization of Unsaturated Carboxylic Acids during the Kolbe Electrolysis

Z-4-Enoic acids partially isomerize to E-configurated products in the Kolbe electrolysis.The results from methyl and deuterium labelled carboxylic acids 2 and 16 support an isomerization via a reversible ring closure to cyclopropylcarbinyl radicals.The double bonds of Z-N-enoic acids with N>/= 5 fully retain their configuration in the Kolbe electrolysis; for N=6,7 cyclic products are formed to some extent, which is in accord with the reactivity of 5- and 6-alkenyl radicals.

SIMPLE METHODS FOR, THE SYNTHESIS OF (E)-4- AND (E)-5-ALKENOIC ACIDS BY THE SN2' TYPE REACTIONS OF γ-VINYL-γ-BUTYROLACTONE AND δ-VINYL-δ-VALEROLACTONE WITH ORGANOCOPPER REAGENTS

γ-Vinyl-γ-butyrolactone and δ-vinyl-δ-valerolactone react regio- and stereoselectively with Grignard reagents in the presence of a copper(I) catalyst or with diorganocuprates to afford (E)-4- and (E)-5-alkenoic acids, respectively, in high yields.Synthetic utility of the former reaction is demonstrated in the simple synthesis of (4E,7Z)-4,7-tridecadienyl acetate.