40269-48-5

Upstream product

• 62414-57-7 (1R,3S,4R)-2,2-dimethyltetrahydrocyclopenta[1,3]dioxol-4-ol 
• 115509-13-2 (3aR,6aR)-2,2-Dimethyl-3a,6a-dihydro-cyclopenta[1,3]dioxol-4-one 
• 104010-72-2 (3aS,6aS)-2,2-dimethyl-3a,6a-dihydro-4H-cyclopenta[d][1,3]dioxol-4-one 
• 1431879-46-7 (+)-3-{[(tert-butyl)dimethylsilyl]oxy}cyclopentane-1,2-diol 
• 1431879-48-9 C₁₄H₂₈O₃Si 
• 25484-60-0 (3aR,4S,6aS)-2,2-Dimethyl-tetrahydro-cyclopenta[1,3]dioxol-4-ol 
• 130980-54-0 (-)-(S)-(cyclopent-2-en-1-yloxy)(1,1-dimethylethyl)dimethylsilane 
• 125851-01-6 (3aS,6R,6aR)-6-methoxy-2,2-dimethyldihydrofuro[3,4-d][1,3]dioxol-4(3aH)-one 
• 4099-85-8 methyl 2,3-O-isopropylidene-D-ribofuranoside 
• 116669-78-4 (4S,5S)-2,2-dimethyl-5-vinyl-[1,3]dioxolane-4-carbaldehyde 
• 67814-68-0 2,3-O-isopropylidene-D-ribofuranose 
• 369647-26-7 (4R,5S)-1-(2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl)-2-propen-1-ol 
• 185622-63-3 (3aS,4S,6R)-2,2-dimethyl-4,6a-dihydro-3aH-cyclopenta[1,3]dioxol-4-ol 
• 595581-70-7 (2S,3S,4R)-1-O-acetyl-2,3-O-isopropylidene-4-vinyl-α-D-erythrofuranose 

Downstream Products

• 149672-39-9 (3aS,6R,6aR)-Hexahydro-cyclopenta[b]furan-2,3a,6-triol 

Relevant academic research and scientific papers

Synthesis of Biologically Active Piperidine Metabolites of Clopidogrel: Determination of Structure and Analyte Development

Clopidogrel is a prodrug anticoagulant with active metabolites that irreversibly inhibit the platelet surface GPCR P2Y12 and thus inhibit platelet activation. However, gaining an understanding of patient response has been limited due to imprecise understanding of metabolite activity and stereochemistry, and a lack of acceptable analytes for quantifying in vivo metabolite formation. Methods for the production of all bioactive metabolites of clopidogrel, their stereochemical assignment, and the development of stable analytes via three conceptually orthogonal routes are disclosed. (Chemical Equation Presented).

Formal synthesis of (-)-cephalotaxine

A formal synthesis of (-)-cephalotaxine (1) by means of a highly stereoselective radical carboazidation process is reported. The synthesis begins with the protected (S)-cyclopent-2-en-1-ol derivative 10 and uses the concept of self-reproduction of a stereogenic center (Schemes5 and 6). For this purpose, the double bond adjacent to the initial chiral center in 10 is converted into an acetonide after stereoselective dihydroxylation. The initial alcohol function is used to build an exocyclic methylene group suitable for the carboazidation process 8→7 (Scheme7). Finally the protected diol moiety is converted back to an alkene (14→15→6) and used for the formation of ring B via a Heck reaction (6→(-)-16; Scheme8). Copyright

AHCY HYDROLASE INHIBITORS FOR TREATMENT OF HYPER HOMOCYSTEINEMIA

The present invention is directed to AHCY inhibitors of formula (I): which are useful in the treatment of diseases characterized by high homocysteine levels, such as Alzheimer's disease. The invention is also directed to pharmaceutical compositions comprising the compounds, and to the use of the compounds and compositions in the treatment of diseases characterized by high homocysteine levels.

USE OF THE IRRITATING PRINCIPAL OLEOCANTHAL IN OLIVE OIL, AS WELL AS STRUCTURALLY AND FUNCTIONALLY SIMILAR COMPOUNDS

The invention provides oleocanthal analogs and methods of using oleocanthals in various formulations including, food additives; pharmaceuticals; cosmetics; animal repellants; and discovery tools for mammalian irritation receptor genes, gene products, alleles, splice variants, alternate transcripts and the like.

USE OF THE IRRITATING PRINCIPAL OLEOCANTHAL IN OLIVE OIL, AS WELL AS STRUCTURALLY AND FUNCTIONALLY SIMILAR COMPOUNDS

The invention provides methods of synthesizing the purified enantiomers of oleocanthal. The invention further provides methods of using oleocanthals in various formulations including, food additives; pharmaceuticals; cosmetics; animal repellants; and discovery tools for mammalian irritation receptor genes, gene products, alleles, splice variants, alternate transcripts and the like.

Syntheses of (-)-oleocanthal, a natural NSAID found in extra virgin olive oil, the (-)-deacetoxy-oleuropein aglycone, and related analogues

(Chemical Equation Presented) Phenolic compounds extracted from extra virgin olive oil have attracted considerable recent attention. One of the components, (-)-oleocanthal (1), an inhibitor of the COX-1 and COX-2 enzymes, possesses similar potency as the NSAID ibuprofen. In this, a full account, we disclose the first- and now second-generation syntheses of both enantiomers of the oleocanthals, as well as the first synthesis of the closely related (-)-deacetoxy-oleuropein aglycone and a series of related analogues for structure activity studies. To demonstrate the utility of the second-generation synthesis, multigram quantities of (-)-oleocanthal were prepared in 10 steps (14% overall yield) from commercially available D-lyxose.

The Mitsunobu reaction in preparing 3-deazapurine carbocyclic nucleosides

The coupling reaction of 4-chloro-1H-imidazo[4,5-c]pyridine (6-chloro-3-deazapurine, 3) with several cyclopentyl derivatives under Mitsunubo reaction conditions provides an efficient entry into N-7 and N-9 substituted 3-deazapurine carbocyclic nucleosides

Synthesis and assignment of absolute configuration of (-)-oleocanthal: A potent, naturally occurring non-steroidal anti-inflammatory and anti-oxidant agent derived from extra virgin olive oils

(Chemical Equation Presented) Effective total syntheses and the assignment of absolute configurations of both the (+)- and (-)-enantiomers of oleocanthal 1 (a.k.a. deacetoxy ligstroside aglycon), the latter derived from extra virgin olive oils and known to be responsible for the back of the throat irritant properties of olive oils, have been achieved. The absolute and relative stereochemistry of the naturally occurring enantiomer (-)-1 proved to be 3S,4E. Both syntheses begin with D-(-)-ribose, proceed in 12 steps, and are achieved with an overall yield of 7%. Both enantiomers proved to be non-steroidal anti-inflammatory and anti-oxidant agents.

Hydroxycyclopentanone derivatives from D-mannose via ring closing metathesis: An improved synthesis of a key intermediate of tricyclo-DNA

A large scale, 10 step synthesis of cyclopentanone 1, starting from the chiral pool compound D-mannose, is described. The synthesis proceeds via a ring closing metathesis reaction as the key step in an overall yield of 23%. Cyclopentanone 1 is a central intermediate for the synthesis of tricyclo-DNA.