99744-77-1

Upstream product

• 76779-67-4 1,2,5,6-di-O-cyclohexylidene-D-mannitol 
• 103959-91-7 (S)-2-(benzyloxy)-2-{(S)-1',4'-dioxaspiro[4.5]decan-2'-yl}ethan-1-ol 
• 108-94-1 cyclohexanone 
• 881377-27-1 5,6-O-cyclohexylidene-gulono-1,4-lactone 
• 229639-21-8 3,4-O-cyclohexylidene-L-(S)-erythrulose 
• 933-40-4 cycloxexanone dimethyl ketal 
• 102335-37-5 5-((2S)-1,4-dioxaspiro[4.5]dec-2-yl)(3S,4R,5S)-3,4-dihydroxy-3,4,5-trihydrofuran-2-one 
• 229639-27-4 (S)-1-(1,4-Dioxa-spiro[4.5]dec-2-yl)-ethane-1,2-diol 
• 99744-80-6 4,5-O-cyclohexylidene-L-arabinose dibenzyl dithioacetal 
• 6614-52-4 5,6-O-cycloheyxlidene-(L)-ascorbic acid 

Downstream Products

• 1193305-57-5 dibenzyl (1S,2R)-2,3-O-cyclohexylidene-1,2,3-trihydroxypropylphosphonate 
• 1193305-51-9 dibenzyl (1R,2R)-2,3-O-cyclohexylidene-1,2,3-trihydroxypropylphosphonate 
• 308795-21-3 (2S,4R,5S)-1,2-O-cyclohexylidene-1,2,5-trihydroxy-5-cyclohexyl-4-methylheptan-3-one 
• 308795-23-5 (2S,4R,5R)-1,2-O-cyclohexylidene-1,2,5-trihydroxy-4-methyl-5-(4-chlorophenyl)pentan-3-one 
• 308795-22-4 (2S,4R,5R)-1,2-O-cyclohexylidene-1,2,5-trihydroxy-4-methyl-5-phenylpentan-3-one 
• 609-06-3 L-xylose 
• 1949-78-6 L-lyxose 
• 24259-59-4 L-ribose 
• 5328-37-0 L-arabinose 

Relevant academic research and scientific papers

An Improved Methodology for the Synthesis of Enantiomerically Pure (S)-2,3-O-Cyclohexylideneglyceraldehyde

An improved methodology to prepare (S)-2,3-O-cyclohexylideneglyceraldehdye is described. Starting from the commercially available (L)-cyclohexylidene protected ascorbic acid the enantiomerically pure aldehyde was synthesized inonly two steps in 41 percent overall yield. 5,6-O-cyclohexylidene-(L)-ascorbic acid -> (S)-2,3-O-cyclohexylideneglyceraldehyde

Synthesis and in vitro biological evaluation of 3-amino-3-deoxydihydrosphingosines and their analogues

The stereoselective synthesis of the 3-amino-3-deoxydihydrosphingosines and their isomeric analogues from dimethyl L-tartrate is described by means of [3,3]-sigmatropic rearrangements and the cross metathesis reaction as a cornerstone of the developed str

Enantioselective total synthesis of callipeltoside A: two approaches to the macrolactone fragment

The enantioselective total synthesis of callipeltoside A is described. Two syntheses of the macrolactone subunit are included: the first relies upon an Ireland-Claisen rearrangement to generate the trisubstituted olefin geometry and the second utilizes an enantioselective vinylogous aldol reaction for this purpose. Enantioselective syntheses of the sugar and chlorocyclopropane side chain fragments are also disclosed. The relative and absolute stereochemistry of this natural product was determined by fragment coupling with the two enantiomers of the side chain fragment.

Pyrogallol and its analogs can antagonize bacterial quorum sensing in Vibrio harveyi

Bacteria can coordinate community-wide behaviors through quorum sensing, that is, the secretion and sensing of autoinducer (AI) molecules. Bacterial quorum sensing is implicated in the regulation of pathologically relevant events such as biofilm formation, bacterial virulence, and drug resistance. Inhibitors of bacterial quorum sensing could therefore be useful therapeutics. Herein we report for the first time the discovery of several pyrogallol compounds as single digit micromolar inhibitors of bacterial quorum sensing in Vibrio harveyi.

Synthetic strategies to epoxydiynes and a key synthon of the neocarzinostatin chromophore

We present herein our recent efforts towards the synthesis of epoxydiynes which represent an unusual structural feature of the neocarzinostatin chromophore. A number of different routes to these epoxydiynes have been explored with varying success. Ultimately a concise and convergent approach was developed, which involved the addition of an allenyl zinc bromide to propargylic ketones/aldehydes followed by epoxide formation. This new protocol enabled us to synthesise a fully elaborated epoxydiyne which will find application for our studies towards the total synthesis of the NCS chromophore. The Royal Society of Chemistry.

EXPEDITIOUS SYNTHESIS OF DPD

This invention provides a practical synthesis route for 4,5-dihydroxypentane-2,3-dione (DPD), an unstable small molecule which is proposed to be the source of universal signaling agents for quorum sensing in bacteria. The synthesis route includes new intermediates and allows preparation of isotopically-labeled DPD and ent-DPD. The method provides sufficient quantities of DPD for study of spontaneous binding of borate to DPD, the signal for the marine bacteria V. harveyi

First stereoselective syntheses of (-)-siphonodiol and (-)- tetrahydrosiphonodiol, bioactive polyacetylenes from marine sponges

The first stereoselective total syntheses of the bioactive marine polyacetylenes (-)-siphonodiol and (-)-tetrahydrosiphonodiol were achieved using highly convergent approaches based on optimized Cadiot-Chodkiewicz and sequential Sonogashira cross-coupling reactions.

An expeditious synthesis of DPD and boron binding studies

(Chemical Equation Presented) A practical synthesis has been developed for DPD (4,5-dihydroxypentane-2,3-dione), an unstable small molecule that is proposed to be the source of universal signaling agents for quorum sensing in bacteria. The synthesis allows preparation of isotopically labeled DPD and ent-DPD as well as detailed studies of spontaneous binding to borate to give the unusual borate complex 6, the signal for marine bacteria such as Vibrio harveyi.

Stereoselective synthesis of syn-α-methyl-β-hydroxy esters

Boron enolates of an ethyl ketone structurally related to erythrulose react with achiral aldehydes in a highly stereoselective fashion to yield 1,2-syn/1,3-syn stereoisomers. Oxidative cleavage of the aldol adducts yields enantiopure O-formylated syn-α-me

Total Synthesis of Symbioramide, a Novel Ca(2+)-ATPase Activator from Symbiodinium sp.

The first total synthesis of symbioramide 1 has been accomplished by the coupling of D-erythro-dihydrosphingosine with an unusual, chiral α-hydroxy-β,γ-unsaturated fatty acid prepared from L-ascorbic acid, and simultaneously established the complete stereostructure of 1 to be (2S,2'R,3R,3'E)-N-(2'-hydroxyoctadec-3'-enoyl)dihydrosphingosine.