15679-27-3

Upstream product

• 51096-08-3 (1S,2S)-cyclohex-4-ene-1,2-dicarboxylic acid 
• 109062-95-5 (1S,2S)-di-(-)-menthyl cyclohex-4-ene-1,2-dicarboxylate 
• 108-05-4 vinyl acetate 
• 13149-04-7 (rac)-trans-4,5-bis(hydroxymethyl)cyclohex-1-ene 
• 88586-06-5 (3aS,7aR)-3a,4,7,7a-tetrahydroisobenzofuran-1(3H)-one 
• 4841-84-3 dimethyl cis-1,2,3,6-tetrahydrophthalate 
• 4841-85-4 trans-1,2-bis(ethoxycarbonyl)-4-cyclohexene 
• 85-43-8 trans-4-Cylohexene-1,2-dicarboxylic anhydride 
• 88586-08-7 (3aS-trans)-3a,4,7,7a-Tetrahydro-1(3H)-isobenzofuranon 
• 34675-24-6 di-L-menthyl fumarate 
• 106-99-0 buta-1,3-diene 
• 17673-68-6 dimethyl trans-cyclohex-4-ene-1,2-dicarboxylate 
• 88-98-2 trans-cyclohex-4-ene-1,2-dicarboxylic acid 
• 104265-86-3 (1R-cis)-6-Chlorcarbonyl-3-cyclohexen-1-carbonsaeure-methylester 

Downstream Products

• 158342-58-6 ((1R,6R)-6-Cyanomethyl-cyclohex-3-enyl)-acetonitrile 
• 117678-57-6 (1S,2S,2'S)-1-(hydroxymethyl)-2-<<(2'-methyl-1-oxobutyl)oxy>methyl>cyclohex-4-ene 
• 117678-58-7 (1S,2S,2'S)-1,2-bis<(2'-methyl-1-oxobutoxy)methyl>cyclohex-4-ene 
• 67337-17-1 ((1S,6S)-6-(benzyloxymethyl)cyclohex-3-enyl)methanol 
• 3205-34-3 (1S,2S)-(–)-1,2-di(hydroxymethyl)cyclohexane 
• 141389-84-6 ((1S*,2S*)-cyclohex-4-ene-1,2-diyl)bis(methylene) dibenzoate 
• 213918-77-5 Methanesulfonic acid (1S,6S)-6-methanesulfonyloxymethyl-cyclohex-3-enylmethyl ester 
• 865306-30-5 (4S,5S)-4,5-bis(iodomethyl)cyclohexene 
• 943003-61-0 C₄₀H₅₀O₂Si₂ 
• 956005-60-0 ((1S,6S)-6-((tert-butyldimethylsilyloxy)methyl)cyclohex-3-enyl)methanol 
• 173827-86-6 (1R,2R)-cyclohexane-1,2-diacetonitrile 
• 173658-50-9 (1S,2S)-cyclohexane-1,2-dimethanol bis(methanesulfonate) 
• 15679-28-4 ((1R,6R)-6-(hydroxymethyl)cyclohex-3-enyl)methanol 
• 82864-75-3 (1R,6R)-6-Hydroxymethyl-cyclohex-3-enecarboxylic acid 

Relevant academic research and scientific papers

Side-chain chiral centers of amino acid and helical-screw handedness of its peptides

Both diastereomeric right-handed (P) and left-handed (M) 310-helices exist in homopeptides having twelve chiral centers at the side-chain bicyclic skeletons. Copyright

ADENYLYL CYCLASE INHIBITORS, PHARMACEUTICAL COMPOSITIONS AND METHOD OF USE THEREOF

The present invention relates to novel adenine based inhibitors of adenylyl cyclase of the formula: wherein X, L, R1, R2, R5 are those defined herein. Compounds of the present invention are useful to treat cardiovascular diseases. The present invention also relates to a method of preventing heart failure by administering an effective amount of compound according to the invention following vascular injury and reperfusion therapy.

Helical structures of bicyclic α-amino acid homochiral oligomers with the stereogenic centers at the side-chain fused-ring junctions

Chiral bicyclic α-amino acid (R,R)-Ab5,6=c with stereogenic centers at the γ-position of fused-ring junctions, and its enantiomer (S,S)-Ab5,6=c, were synthesized. The CD spectra of (R,R)-Ab5,6=c oligomers indicated that th

[6+5] FUSED BICYCLES AS A THROMBIN ANTAGONIST, PROCESS FOR PREPARATION THEREOF AND PHARMACEUTICAL COMPOSITIONS CONTAINING THE BICYCLES

The present invention relates to the new [6+5] fused bicycle derivatives, pharmaceutically acceptable salts or isomers thereof, processes for preparing the same, and pharmaceutical compositions comprising the same. The [6+5] fused bicycle derivatives can antagonize the thrombin receptor and thus may be effectively used for the treatment and prevention of thrombus, platelet aggregation, atherosclerosis, restenosis, blood coagulation, hypertension, arrhythmia, angina pectoris, heart failure, inflammation and cancer when used alone or with other cardiovascular agents.

Synthesis and in vivo evaluation of 3,4-disubstituted gababutins

A range of 3,4-alkylated five-membered ring derivatives of gabapentin were synthesised. One compound (21) had an excellent level of potency against α2δ and was profiled in in vivo models of pain and anxiety.

Olefin metathesis: A reversible stimulus for a conformational switch

A ring-closing olefin metathesis (RCM) to an eight-membered ring is suitable to induce a conformational switch of a 2,3,6,7-tetrasubstituted cis-decalin. The double-ring flip of the decalin scaffold can be reversed by a ring-opening metathesis. The corres

Asymmetric Diels-Alder reaction of 1,3-butadienes with (-)-dimenthyl fumarate in the presence of BBr3 and BBr3·OEt 2

Asymmetric synthesis of substituted cyclohexenes was performed by [4+2]-cycloaddition of (-)-dimenthyl fumarate to 1,3-butadienes in the presence of BBr3 and BBr3·OEt2. The latter are efficient catalysts for this reaction.

Synthesis of enantiomerically pure bis(hydroxymethyl)-branched cyclohexenyl and cyclohexyl purines as potential inhibitors of HIV

The synthesis of the enantiomerically pure bis(hydroxymethyl)-branched cyclohexenyl and cyclohexyl purines is described. Racemic trans-4,5-bis(methoxycarbonyl)cyclohexene [(±)-6] was reduced with lithium aluminum hydride to give the racemic diol (±)-7. Resolution of (±)-7 via a transesterification process using lipase from Pseudomonas sp. (SAM-II) gave both diols in enantiomerically pure form. The enantiomerically pure diol (S,S)-7 was benzoylated and epoxidized to give the epoxide 9. Treatment of the epoxide 9 with trimethylsilyl trifluoromethanesulfonate and 1,5-diazabicyclo[5.4.0]undec-5-ene followed by dilute hydrochloric acid gave (1R,4S,5R)-4,5-bis[(benzoyloxy)methyl]1-hydroxycyclohex-2-ene (10). Acetylation of 10 gave (1R,4S,5R)-1-acetoxy-4,5-bis[(benzoyloxy)methyl]cyclohex-2-ene (11). (1R,4S,5R)-1-Acetoxy-4,5-bis[(benzoyloxy)methyl]cyclohex-2-ene (11) was converted to the adenine derivative 12 and guanine derivative 13 via palladium(0)-catalyzed coupling with adenine and 2-amino-6-chloropurine, respectively. Hydrogenation of 12 and 13 gave the corresponding saturated adenine derivative 14 and guanine derivative 15. (1R,4S,5R)-4,5-Bis[)benzoyloxy)methyl]-1-hydroxycyclohex-2-ene (10) was converted to the adenine derivative 16 and guanine derivative 17 via coupling with 6-chloropurine and 2-amino-6-chloropurine, respectively, using a modified Mitsunobu procedure. Hydrogenation of 16 and 17 gave the corresponding saturated adenine derivative 18 and guanine derivative 19. Compounds 12-19 were evaluated for activity against human immunodeficiency virus (HIV), but were found to be inactive. Further biological testings are underway.

Complete relative stereochemistry of maitotoxin

By addressing the relative stereochemistry of the four acyclic portions via organic synthesis, the complete relative stereochemistry of maitotoxin (MTX) has been established as 1B. The relative stereochemistry of the C.1-C.15 portion was elucidated via a two-phase approach: (1) the synthesis of the eight diastereomers possible for model C, representing the C.1-C.11 portion, and the eight diastereomers possible for model D, representing the C.11-C.15 portion, and the comparison of their proton and carbon NMR characteristics with those of MTX, concluding that 9 and 35 represent the relative stereochemistry of the corresponding portions of MTX; (2) the synthesis of the two remote diastereomers 51 and 52, and comparison of their proton and carbon NMR characteristics with those of MTX, concluding that 51 represents the relative stereochemistry of the C.1-C.15 portion of MTX. The relative stereochemistry of the C.35-C.39, C.63-C.68, and C.134-C.142 acyclic portions was established via (1) the synthesis of the 8, 8, and 16 diastereomers possible for models E, F, and G, respectively, and (2) the comparison of their proton and carbon NMR characteristics with those of MTX, concluding that 81, 117, and 187, respectively, represent the relative stereochemistry of the corresponding portions of MTX. Some biogenetic considerations have been given to speculate on the absolute configuration of MTX. The vicinal proton coupling constants observed for models 51, 81, 117, and 187 were used to elucidate their preferred solution conformation. Assembling the preferred solution conformations found for the four acyclic portions allows one to suggest that the approximate global conformation of MTX is represented by the shape of a hook, with the C.35-C.39 portion being its curvature. MTX appears to be conformationally relatively rigid, except for conformational flexibility around the C.7-C.9 and C.12-C.14 portions. On the basis of the experimental results gained in the current work, coupled with those in the AAL-toxin/fumonisin area, it has been pointed out that the structural properties of 51, 81, 117, 187 and their diastereomers are inherent to the specific stereochemical arrangement of the small substituents on the carbon backbone and are independent from the rest of the molecule. Thus, it has been suggested that each of these diastereomers has the capacity to install a unique structural characteristic through a specific stereochemical arrangement of substituents on the carbon backbone, and that fatty acids and related classes of compounds may be able to carry specific information and serve as functional materials in addition to structural materials.

Total synthesis of Taxol. 2. Construction of A and C ring intermediates and initial attempts to construct the ABC ring system

A method for the formation of Taxol's ABC ring system has been developed. General methods for the synthesis of versatile synthons for Taxol's A ring (8) and C ring (55) are presented. A model study using a simplified C ring synthon (17) confirmed the viability of the sequential Shapiro-McMurry strategy for formation of Taxol's B ring. Careful exploration of the chemistry of various A-B ring conjugates allowed the development of a successful method for formation of the B ring in a more functionalized system.