7056-84-0

Upstream product

• 542-28-9 3,4,5,6-tetrahydro-2H-pyran-2-one 
• 131216-47-2 5-(tert-butyldiphenylsilyloxy)pentanal 
• 928-90-5 5-hexyl-1-ol 
• 85388-16-5 (E)-pentadec-4-en-1-ol 
• 72443-47-1 hexadec-5-yn-1-ol 
• 112-29-8 1-bromo dodecane 
• 2050-77-3 Iododecane 
• 1720-37-2 2-(hex-5-yn-1-yloxy)tetrahydro-2H-pyran 
• 56218-65-6 (E)-5-hexadecenyl acetate 
• 99142-09-3 (1S,2R,3R)-2-Decyl-3-tributylstannanyl-cyclohexanol 
• 99142-09-3 (1R,2R,3R)-2-Decyl-3-tributylstannanyl-cyclohexanol 
• 4221-03-8 5-hydroxypentanal 
• 1026489-01-9 tert-Butyl-[((E)-hexadec-5-enyl)oxy]-diphenyl-silane 
• 99142-11-7 (E)-Hexadec-5-enal 

Downstream Products

• 89102-35-2 (5S,6R)-6-hydroxy-5-hexadecanolide 
• 1609262-98-7 (5R,6S)-6-hydroxy-5-hexadecanolide-4-nitrobenzoate 
• 1609262-97-6 (5S,6R)-6-hydroxy-5-hexadecanolide 4-nitrobenzoate 
• 89102-36-3 (5R,6S)-6-hydroxyhexadecan-5-olide 
• 81792-36-1 racemic erythro 6-acetoxy-5-hexadecanolide 
• 89102-35-2 (5R*,6S*)-6-hydroxyhexadecan-5-olide 
• 81792-36-1 racemic threo 6-acetoxy-5-hexadecanolide 

Relevant academic research and scientific papers

Asymmetric total synthesis of all four isomers of 6-acetoxy-5- hexadecanolide: The major component of mosquito oviposition attractant pheromones

An asymmetric total synthesis of (5S,6R)-(+)-erythro-6-acetoxy-5- hexadecanolide 1a has been accomplished from readily available hex-5-yn-1-ol via Shi's asymmetric epoxidation as the key step, in eight steps with an overall yield of 33.5%. In addition, the stereoselective synthesis of all four isomers of 6-acetoxy-5-hexadecanolide 1a-1d were obtained via Sharpless asymmetric dihydroxylation and Mitsunobu reaction as the key steps with overall yields of 16.5-21.2%, respectively.

Metathesis syntheses of pheromones or their components

The present invention relates to metathesis syntheses for insect sex-attractant pheromones or their components, such as E-5-decenyl acetate, the major component of the Peach Twig Borer pheromone; (5R,6S)-6-acetoxy-5-hexadecanolide, the mosquito oviposition attractant pheromone; E9,Z11-hexadecadienal, the pecan nut casebearer moth pheromone; 9-tetradecenyl formate, an analog of the Diamondback Moth (DBM) pheromone; 11-tetradecenyl acetate, the Omnivorous Leafroller (OLR) pheromone; E-4-tridecenyl acetate, the major component of the Tomato Pinworm (TPW) pheromone; E,E-8,10-dodecadienol, the Codling Moth (CM) pheromone. The syntheses preferably employ a Class I-IV metathesis catalyst, entail few reaction steps, use generally commercially available starting materials, and have relatively short process times. These syntheses produce good yields without the need for expensive or sophisticated equipment. The invention also provides an inexpensive route for producing omega-haloalkenols by cross-metathesizing alpha-omega-diacetoxy alkenes and alpha-omega-dihalides to yield omega-haloalkenols, which are easily converted into omega-haloalkanols under traditional hydrogenation methods.

Metathesis syntheses of pheromones or their components

The present invention relates to metathesis syntheses for insect sex-attractant pheromones or their components, such as E-5-decenyl acetate, the major component of the Peach Twig Borer pheromone; (5R, 6S)-6-acetoxy-5-hexadecanolide, the mosquito oviposition attractant pheromone; E9, Z11-hexadecadienal, the pecan nut casebearer moth pheromone; 9-tetradecenyl formate, an analog of the Diamondback Moth (DBM) pheromone; 11-tetradecenyl acetate, the Omnivorous Leafroller (OLR) pheromone; E-4-tridecenyl acetate, the major component of the Tomato Pinworm (TPW) pheromone; E,E-8,10-dodecadienol, the Codling Moth (CM) pheromone. The syntheses preferably employ a Class I-IV metathesis catalyst, entail few reaction steps, use generally commercially available starting materials, and have relatively short process times. These syntheses produce good yields without the need for expensive or sophisticated equipment. The invention also provides an inexpensive route for producing omega-haloalkenols by cross-metathesizing alpha-omega-diacetoxy alkenes and alpha-omega-dihalides to yield omega-haloalkenols, which are easily converted into omega-haloalkanols under traditional hydrogenation methods.

A general synthetic route towards γ- and δ-lactones. Total asymmetric synthesis of (-)-muricatacin and the mosquito oviposition pheromone (5R, 6s)- 6-acetoxy-hexadecanolide

Five (or six) membered asymmetric lactones are synthesized from γ- butyrolactone (or δ-valerolactone) in a straightforward way using the following reaction sequence: reduction, Wittig-Schlosser coupling, Sharpless asymmetric dihydroxylation, oxidation and lactonization. Thus, (-)muricatacin is synthesized in six steps (43% overall yield). Furthermore, (5R,6S)-6- acetoxy-hexadecanolide is prepared in eight steps (38% overall yield) via a carbonate ester, utilizing a novel lactonization with inversion of stereochemistry.

Oxidative Grob Fragmentation of γ-Tributylstannyl Alcohols with a Combination of Iodosylbenzene, Dicyclohexylcarbodiimide, and Boron Trifluoride

Exposure of cyclic γ-stannyl alcohols, prepared from cyclic vinyl ketones, to a combination of iodosylbenzene, dicyclohexylcarbodiimide, and boron trifluoride-diethyl ether in dichlorometane undergoes an oxidative Grob fragmentation to give unsaturated carbonyl compounds.The dicyclohexylcarbodiimide in this reaction apparently activates iodosylbenzene and decreases Lewis acidity of boron trifluoride.The fact that the iodine(III)-mediated Grob fragmentation proceeds stereospecifically suggests the fragmentation is concerted.The fragmentation, combined with conjugate addition of (tributylstannyl)lithium and reduction or alkylation, offers an efficient procedure for the reductive and alkylative ring opening of cyclic vinyl ketones.Since cis-benzyl ether 36, after quenching of the reaction mixture with aqueous NH4Cl, afforded the chlorostannane 37, the reaction mechanism involving the formation of iodine(III) species 32 with two oxygen ligands at iodine proposed.

Stereochemistry of an Oxidative 1,4-Fragmentation of γ-Stannyl Alcohols with a Hypervalent Organoiodine Compound and the Synthesis of erythro-6-Acetoxyhexadecan-5-olide

Iodine(III)-mediated oxidative 1,4-fragmentation of the 2,3-trans- and 2,3-cis-3-stannyl alcohols, (6a,b) and (6c), proceeds stereospecifically to give the E- and Z-enals, (7) and (8), respectively, and stereoselective synthesis of the mosquito pheromone,

SRS-A antagonists

There are described pharmacologically active compounds, useful in the treatment of allergic/inflammatory disorders involving SRS-A as causal mediator and which, in free acid form, are of formula I, STR1 in which R1 is (i) an aliphatic, saturated or unsaturated hydrocarbyl radical of up to 20 carbon atoms, unsubstituted or substituted by at least one substituent selected from halogen, hydroxy, C3-6 alkoxy, C3-6 cycloalkyl, aryl or heteroaryl, the cycloalkyl, aryl or heteroaryl being unsubstituted or substituted by at least one substituent selected from hydroxy, halogen and alkyl, alkenyl or alkynyl of up to 10 carbon atoms, (ii) cycloalkyl of 3 to 8 carbon atoms unsubstituted or substituted by alkyl, alkenyl or alkynyl of up to 16 carbon atoms, or (iii) aryl or heteroaryl, unsubstituted or substituted by hydroxyl, C1-4 alkoxy, halogen or alkyl, alkenyl or alkynyl of up to 16 carbon atoms; and R2 is (i) alkyl, cycloalkyl or alkenyl of up to 10 carbon atoms, unsubstituted or substituted by one or more substituents selected from aryl, cycloalkyl, halogen, hydroxy, NHR3 and COX, where R3 is H, C1-4 alkyl, aryl or an amino acid residue or COX, and X is OH, C1-4 alkyl, NH2 or an amino acid residue, or (ii) aryl or heteroaryl, unsubstituted or substituted by one or more substituents selected from C1-4 alkyl, C1-4 alkoxy, C2-5 acyl, halogen, hydroxy, carboxy, nitro, trihalomethyl, phenyl, C1-4 acylamino and NHR4, where R4 is hydrogen or C1-4 alkyl; and Y is --S--, --SO-- or --SO2 --, with the proviso that when --YR2 is glutathionyl, cysteinyl or cysteinylglycinyl, then R1 is other than an unsubstituted alkatetraenyl or alkapentaenyl radical of 12 to 16 carbon atoms.