104863-66-3

Upstream product

• 2528-61-2 Heptanoic acid chloride 
• 6638-79-5 N,O-dimethylhydroxylamine*hydrochloride 
• 111-14-8 oenanthic acid 
• 1117-97-1 N,0-dimethylhydroxylamine 
• 107-30-2 chloromethyl methyl ether 
• 334-19-0 heptanoic acid fluoride 

Downstream Products

• 7018-92-0 2,5-Undecanedione 
• 334698-83-8 N,N-diethyl-2-heptanoyl-6-methoxybenzamide 
• 26672-63-9 1-(4-dimethylamino-phenyl)-heptan-1-one 
• 35891-70-4 myriocin 
• 462-18-0 tridecan-7-one 
• 916166-24-0 1,1,1-trideuterio-2-octanone 
• 1535171-12-0 ethyl (3S)-3-(dimethylphenylsilyl)-4,4-dideutero-2-ethoxycarbonyl-5-oxoundecanoate 
• 1268368-86-0 (S)-3-(benzyloxy)-1-(tert-butyldimethylsilyloxy)tridec-5-yn-7-one 
• 3400-24-6 N-methylheptanamide 
• 389807-40-3 (2'E,1'S,6R,3aS,6aR)-6-[10',10'-ethylenedioxy-1'-(4-methoxybenzyloxy)-hexadec-2'-en-1'-yl]-3a-(4-methoxybenzyloxymethyl)-2-phenyl-6,6a-dihydro-3aH-furo[3,4-d]oxazol-4-one 
• 389807-42-5 (2'E,1'S,3S,4R,5R)-3-benzamido-4-hydroxy-3-hydroxymethyl-5-(1'-hydroxy-10'-oxo-hexadec-2'-en-1'-yl)-2-oxo-tetrahydrofuran 
• 145401-47-4 sphingofungin E 
• 211691-24-6 (2E,1'S,6R,3aS,6aR)-6-[10',10'-ethylenedioxy-1'-(4''-methoxybenzyloxy)hexadec-2'-en-1'-yl]-3a-methyl-2-phenyl-6,6a-dihydro-3aH-furo[3,4-d]oxazol-4-one 
• 145401-48-5 sphingofungin F 

Relevant academic research and scientific papers

A one-flask synthesis of weinreb amides from chiral and achiral carboxylic acids using the deoxo-fluor fluorinating reagent

(Matrix presented) The reagent [bis(2-methoxyethyl)amino]sulfur trifluoride (Deoxo-Fluor reagent) converts carboxylic acids to the corresponding acid fluorides, which then react with N,N-dimethylhydroxylamine to give the corresponding Weinreb amides in high yields. The reaction proceeds without racemization when optically active acids are used as the starting material. This method is operationally simple and provides the products in high purity.

Reductive N-O cleavage of Weinreb amides by sodium in alumina and silica gels: synthetic and mechanistic studies

The use of sodium in alumina and silica gels for the reductive cleavage of the N-O bond of N-methoxy-N-methylamides, commonly referred to as Weinreb amides, has been investigated. This method reduces a diverse set of Weinreb amides with different function

An efficient enantioselective synthesis of (2R)-hydroxymethyl glutamic acid and an approach to the (2R)-hydroxymethyl-substituted sphingofungins

We have developed a short enantioselective synthesis of (2R)-hydroxymethyl glutamic acid (HMG) starting from Garner's aldehyde using an alkylidene carbene 1,5-CH insertion as a method to construct the quaternary stereocenter. A variety of conditions were examined for the oxidative cleavage of the key cyclopentene intermediate and we found that RuCl3/NaIO4 led directly to the desired amino bis-acid product. We were also able to show that oxidative cleavage of the cyclopentene 1,5-CH insertion product could be used to produce the amino acid-containing skeleton of the sphingofungin family of natural products.

IONIZABLE CATIONIC LIPID FOR RNA DELIVERY

What is described is a compound of formula I consisting of a compound in which R1 is a branched chain alkyl consisting of 10 to 31 carbons; R2 is a linear alkyl, alkenyl, or alkynyl consisting of 2 to 20 carbons; L1 and L2 are the same or different, each a linear alkylene of 1 to 20 carbons or a linear alkenylene of 2 to 20 carbons; X1 is S or O; R3 is a linear or branched alkylene consisting of 1 to 6 carbons; and R4 and R5 are the same or different, each a hydrogen or a linear or branched alkyl consisting of 1 to 6 carbons; or a pharmaceutically acceptable salt thereof.

IONIZABLE CATIONIC LIPID FOR RNA DELIVERY

What is described is a compound of formula I consisting of a compound in which R1 is a branched chain alkyl consisting of 10 to 31 carbons;R2 is a linear alkyl, alkenyl, or alkynyl consisting of 2 to 20 carbons, or a branched chain alkyl consisting of 10 to 31 carbons;L1 and L2 are the same or different, each a linear alkane of 1 to 20 carbons or a linear alkene of 2 to 20 carbons;X1 is S or O;R3 is a linear or branched alkylene consisting of 1 to 6 carbons; andR4 and R5 are the same or different, each a hydrogen or a linear or branched alkyl consisting of 1 to 6 carbons; or a pharmaceutically acceptable salt thereof.

A facile synthesis of 5,5-dideutero-4-dimethyl(phenyl)silyl-6-undecyl- tetrahydropyran-2-one as a deuterium labeled synthon for (-)-tetrahydrolipstatin and (+)-δ-hexadecanolide

Deuterium-labeled biologically active compounds are gaining importance because they can be utilized as tracers or surrogate compounds to understand the mechanism of action, absorption, distribution, metabolism, and excretion. Deuterated drug molecules (heavy drugs) become novel as well as popular because of better stability and bioavailability compared with their hydrogen analogs. Labeling of organic molecules with deuterium at specific positions is thus gaining popularity. In this work, we have exploited a highly regioselective and enantioselective direct Michael addition of methyl-d3 alkyl ketones to dimethyl(phenyl)silylmethylene malonate that was catalyzed by (S)-N-(2-pyrrolidinylmethyl)pyrrolidine/trifluoroacetic acid/ D2O combination with high yield and isotopic purity. The 5,5-dideutero-4- dimethyl(phenyl)silyl-6-undecyl-tetrahydropyran-2-one was obtained from the adduct of methyl-d3 undecanyl ketone and dimethyl(phenyl) silylmethylene malonate by a silicon controlled diastereoselective ketone reduction, lactonization, and deethoxycarbonylation. The dideuterated silylated tetrahydropyran-2-one is the precursor for geminal 2H 2-labeled (+)-4-hydroxy-6-undecyl-tetrahydropyran-2-one, an advanced intermediate for gem-dideutero (-)-tetrahydrolipstatin and (+)-δ- hexadecanolide syntheses. Copyright

[Bis(2-methoxyethyl)amino]sulfur Trifluoride, the Deoxo-Fluor Reagent: Application toward One-Flask Transformations of Carboxylic Acids to Amides

The use of the Deoxo-Fluor reagent is a versatile method for acyl fluoride generation and subsequent one-flask amide coupling. It provides mild conditions and facile purification of the desired products in good to excellent yields. We have explored the utility of this reagent for the one-flask conversion of acids to amides and Weinreb amides and as a peptide-coupling reagent.

Total synthesis of myriocin

A concise, stereocontrolled synthesis of myriocin was achieved. Key features involve diastereoselective oxazoline formation catalyzed by palladium(0), MgBr2-promoted allylic stannane addition, and palladium(0)-catalyzed coupling of a vinyl iodide with an organozinc reagent.

Total synthesis of sphingofungin F.

[reaction: see text] A concise, stereocontrolled synthesis of sphingofungin F was achieved. Key features involve diastereoselective oxazoline formation catalyzed by palladium(0), MgBr(2)-promoted gamma-alkoxy allylic stannane addition, and palladium(0)-ca

gem-diacetates as carbonyl surrogates for asymmetric synthesis. Total syntheses of sphingofungins E and F

The equivalent of an asymmetric addition to a carbonyl group with a stabilized anion is accomplished by discriminating between the enantiotopic C-O single bonds of a gem-diacetate. In this way, enantioselective total syntheses of two antifugal agents, sph