32556-71-1

Usage

InChI:InChI=1/C8H14O/c1-3-5-6-7-8(9)4-2/h2,8-9H,3,5-7H2,1H3/t8-/m1/s1

Upstream product

• 818-72-4 1-Octyn-3-ol 
• 27593-19-7 oct-1-yn-3-one 
• 53210-14-3 n-pentyl trimethylsilylethynyl ketone 
• 42541-99-1 (R)-(E)-1-Iodo-1-octene-3-ol 
• 125340-70-7 (2S,3S)-2-Chloromethyl-3-pentyl-oxirane 
• 131802-37-4 (2S,3S)-1-chloro-2,3-O-isopropylidenedioxyoctane 
• 129974-79-4 (RS)-1-Pentylpropynyl (L)-2-chloropropanoate 
• 129974-79-4 (RS)-1-Pentylpropynyl (D)-2-chloropropanoate 
• 125340-70-7 (2R-trans)-3-pentyloxirane methyl chloride 
• 54315-38-7 (S)-oct-1-yn-3-yl acetate 
• 54315-33-2 3-acetoxy-1-octyne 
• 123-62-6 propionic acid anhydride 
• 66-25-1 hexanal 
• 92134-09-3 ((2S,3S)-3-(pent-4-en-1-yl)oxiran-2-yl)methanol 

Downstream Products

• 98892-41-2 {3-[(1R,2S,3S,4S)-3-((R)-3-Hydroxy-oct-1-ynyl)-7-oxa-bicyclo[2.2.1]hept-2-ylmethyl]-phenoxy}-acetic acid 
• 98892-38-7 {3-[(1S,2R,3R,4R)-3-((R)-3-Hydroxy-oct-1-ynyl)-7-oxa-bicyclo[2.2.1]hept-2-ylmethyl]-phenoxy}-acetic acid methyl ester 
• 98892-41-2 {3-[(1S,2R,3R,4R)-3-((R)-3-Hydroxy-oct-1-ynyl)-7-oxa-bicyclo[2.2.1]hept-2-ylmethyl]-phenoxy}-acetic acid 
• 98892-38-7 {3-[(1R,2S,3S,4S)-3-((R)-3-Hydroxy-oct-1-ynyl)-7-oxa-bicyclo[2.2.1]hept-2-ylmethyl]-phenoxy}-acetic acid methyl ester 
• 113332-13-1 {3-[(1S,2S,3S,4R,1'S,3'R,4'R)-3'-((S)-3-Hydroxy-oct-1-ynyl)-[2,2']bi[7-oxa-bicyclo[2.2.1]heptyl]-3-ylmethyl]-phenoxy}-acetic acid methyl ester 
• 113332-13-1 {3-[(1S,3S,4R,1'S,2'R,3'R,4'R)-3'-((R)-3-Hydroxy-oct-1-ynyl)-[2,2']bi[7-oxa-bicyclo[2.2.1]heptyl]-3-ylmethyl]-phenoxy}-acetic acid methyl ester 
• 98892-39-8 {3-[(1S,2R,3S,4R)-3-((R)-3-Hydroxy-oct-1-ynyl)-bicyclo[2.2.1]hept-2-ylmethyl]-phenoxy}-acetic acid 
• 98892-36-5 {3-[(1R,2S,3R,4S)-3-((R)-3-Hydroxy-oct-1-ynyl)-bicyclo[2.2.1]hept-2-ylmethyl]-phenoxy}-acetic acid methyl ester 
• 98892-39-8 {3-[(1R,2S,3R,4S)-3-((R)-3-Hydroxy-oct-1-ynyl)-bicyclo[2.2.1]hept-2-ylmethyl]-phenoxy}-acetic acid 
• 98892-36-5 {3-[(1S,2R,3S,4R)-3-((R)-3-Hydroxy-oct-1-ynyl)-bicyclo[2.2.1]hept-2-ylmethyl]-phenoxy}-acetic acid methyl ester 
• 98892-36-5 {3-[(1S,2R,3S,4R)-3-((S)-3-Hydroxy-oct-1-ynyl)-bicyclo[2.2.1]hept-2-ylmethyl]-phenoxy}-acetic acid methyl ester 
• 98892-37-6 {3-[(1R,2R,3S,4S)-3-((S)-3-Hydroxy-oct-1-ynyl)-bicyclo[2.2.1]hept-5-en-2-ylmethyl]-phenoxy}-acetic acid methyl ester 
• 98892-38-7 {3-[(1R,2S,3S,4S)-3-((S)-3-Hydroxy-oct-1-ynyl)-7-oxa-bicyclo[2.2.1]hept-2-ylmethyl]-phenoxy}-acetic acid methyl ester 
• 125340-81-0 (R)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid (S)-1-ethynyl-hexyl ester 

Relevant academic research and scientific papers

Total synthesis of lipoxin A4 and lipoxin B4 from butadiene

The total synthesis of LXA4 and LXB4 has been achieved starting from butadiene via palladium catalyzed telomerization. Sharpless catalytic AE and C-2 inversion of the 2(S),3(S)-epoxy alcohols, using Myers CO2/Cs2CO3 procedure, generated the asymmetric centers. The flexibility of the strategy allows an easy access to the linear eicosanoids. (C) 2000 Elsevier Science Ltd.

Gold-Catalyzed Synthesis of Chiral Cyclopentadienyl Esters via Chirality Transfer

Efficient access to chiral cyclopentadienyl esters from readily accessible chiral enynyl ester substrates is developed. Typically high levels of chirality transfer realized in this homogeneous gold catalysis are attributed to the intermediacy of a chiral bent allene gold complex. Cyclopentadienyl esters can be prepared in good yields and with excellent enantiomeric excesses. The synthetic utilities of the chiral cyclopentadienyl esters are demonstrated by the Diels-Alder reactions, fluorination, alkylation, and epoxidation without any notable erosion of enantiopurity.

Synthetic method for (S)-Virol A from water hemlock extract

The invention relates to a synthetic method for (S)-Virol A from a polyacetylene water hemlock extract. The synthetic method for (S)-Virol A from the polyacetylene water hemlock extract is an asymmetric synthetic method, and comprises the following steps: firstly, under catalysis of a chiral ligand, methyl propiolate and dimethyl zinc are reacted to prepare an alkynyl zinc reagent, hexanal is subjected to asymmetric addition reaction to obtain a chiral intermediate (S)-4- hydroxy-2-alkyne methyl nonanoate, through ester group removal to obtain acetylene, the processed intermediate is coupled with vinylidene chloride, then selective reduction is carried out to obtain a product, and finally the product is coupled with 4,6-diyne-1-heptanol to obtain the (S)-Virol A. The flow of the method is simple and easy to realize, and the method is environmental-friendly.

A general strategy toward the total synthesis of C17 polyacetylenes virols A and C

A general strategy toward the total synthesis of biologically important C17 polyacetylenes family such as virols A and C has been developed, which employed the (R, R)-ProPhenol/Zn complex-catalyzed highly stereoselective direct addition of propiolate to aliphatic aldehydes as the key step for constructing chiral (S)-alkynol units. Besides, chiral alkynol units in other C17 polyacetylenes were also synthesized based on the protocol developed.

Coupling biocatalysis and click chemistry: One-pot two-step convergent synthesis of enantioenriched 1,2,3-triazole-derived diols

A fully convergent one-pot two-step synthesis of different chiral 1,2,3-triazole-derived diols in high yields and excellent enantio- and diastereoselectivities has been achieved under very mild conditions in aqueous medium by combining a single alcohol dehydrogenase (ADH) with a Cu-catalysed 'click' reaction. The Royal Society of Chemistry 2013.

One-pot deracemization of sec-alcohols: Enantioconvergent enzymatic hydrolysis of alkyl sulfates using stereocomplementary sulfatases

Hand in hand: The title transformation was achieved using a pair of sulfatases acting through inversion and retention of configuration on opposite substrate enantiomers. Using Pseudomonas aeruginosa arylsulfatase PAS with alkylsulfatase PISA1 in one-pot l

Novel, stereoselective and stereospecific synthesis of allenylphosphonates and related compounds via palladium-catalyzed propargylic substitution

We have developed a novel method for the synthesis of allenylphosphonates and related compounds based on a palladium(0)-catalyzed reaction of propargylic derivatives with H-phosphonate, H-phosphonothioate, H-phosphonoselenoate, and H-phosphinate esters. The reaction is stereoselective and stereospecific, and provides a convenient entry to a vast array of allenylphosphonates and their analogues with diverse substitution patterns in the allenic moiety and at the phosphorus center. Some mechanistic aspects of this new reaction were also investigated. Copyright

Palladium-catalyzed propargylic substitution with phosphorus nucleophiles: Efficient, stereoselective synthesis of allenylphosphonates and related compounds

A new, efficient method is developed, based on a palladium(0)-catalyzed reaction of propargylic derivatives with various phosphorus nucleophiles, to produce allenylphosphonates and their analogues with defined stereochemistry in the allenic and the phosph

Total synthesis of halicholactone and neohalicholactone

New total syntheses of the marine oxylipins halicholactone and neohalicholactone are presented. The key building blocks were synthesized utilizing chemoenzymatic methods.

Kinetic resolution of propargylic alcohols catalyzed by benzotetramisole

(Chemical Equation Presented) Kinetic resolution of variously substituted secondary propargylic alcohols catalyzed by benzotetramisole (BTM) proceeds with selectivity factors up to 32, the highest ever achieved with nonenzymatic catalysts for this class o