89527-11-7

Upstream product

• 98-88-4 benzoyl chloride 
• 821-09-0 n-Pent-4-enyl alcohol 
• 29264-40-2 5-pentenylbenzoate 

Downstream Products

• 664997-56-2 Benzoic acid (R)-3-oxiranyl-propyl ester 
• 20350-15-6 (+)-brefeldin A 
• 664997-48-2 Benzoic acid (S)-4-hydroxy-pentyl ester 
• 231291-69-3 (S)-4-Benzyloxy-pentan-1-ol 
• 664997-49-3 ((S)-1-Methyl-hex-5-ynyloxymethyl)-benzene 
• 664997-51-7 (E)-(S)-6-benzyloxy-hept-1-ene 
• 664997-50-6 C₁₄H₂₁BO₃ 
• 664997-52-8 (3R,4S)-3-[(E)-(R)-4-Benzyloxy-1-(tert-butyl-dimethyl-silanyloxy)-but-2-enyl]-4-((E)-(S)-6-benzyloxy-hept-1-enyl)-cyclopentanone 
• 664997-57-3 (1R,3R,4S)-3-[(E)-(R)-4-Benzyloxy-1-(tert-butyl-dimethyl-silanyloxy)-but-2-enyl]-4-((E)-(S)-6-benzyloxy-hept-1-enyl)-cyclopentanol 
• 664997-53-9 (1S,3R,4S)-3-[(E)-(R)-4-Benzyloxy-1-(tert-butyl-dimethyl-silanyloxy)-but-2-enyl]-4-((E)-(S)-6-benzyloxy-hept-1-enyl)-cyclopentanol 
• 664997-58-4 C₄₂H₆₈O₄Si₂ 
• 664997-54-0 C₄₂H₆₈O₄Si₂ 

Relevant academic research and scientific papers

3,6-DIAMINO-PYRIDAZIN-3-YL DERIVATIVES, PHARMACEUTICAL COMPOSITIONS CONTAINING THEM AND THEIR USES AS PRO-APOPTOTIC AGENTS

Compounds of formula (I) wherein Het1, Het2, R1, R2 and R3 are as defined in the description. Medicaments.

Synthesis of the 5-fluoro-4-hydroxypentyl side chain metabolites of synthetic cannabinoids 5F-APINACA and CUMYL-5F-PINACA

An efficient method for the construction of the 5-fluoro-4-hydroxypentyl side chain common to a number of synthetic cannabinoid metabolites was developed. A series of hydroxyl protecting groups was examined to assess the viability as orthogonal protecting

Switching the reaction pathways of electrochemically generated β-haloalkoxysulfonium ions - Synthesis of halohydrins and epoxides

β-Haloalkoxysulfonium ions generated by the reaction of electrogenerated Br+ and I+ ions stabilized by dimethyl sulfoxide (DMSO) reacted with sodium hydroxide and sodium methoxide to give the corresponding halohydrins and epoxides, respectively, whereas the treatment with triethylamine gave α-halocarbonyl compounds.

Enantioselective total synthesis of (+)-brefeldin A and 7-epi-brefeldin A

A convergent enantioselective route to brefeldin A (BFA) and 7-epi-BFA was developed. The key C-4/C-5 chiral centers were established by using chiral auxiliary induced intermolecular asymmetric aldolization in the presence of TiCl4 and TMEDA. The results with the thiazolidinethione/TiCl 4 mediated intermolecular asymmetric aldolization added some new information about the scope and limitations to the existing knowledge of that type of reactions (which so far was essentially limited to the reactions with N-propionyl thiazolidinethiones). During the course a method for protecting the liable aldol hydroxyl groups by using inexpensive TBSCl in DMF with 2, 6-lutidine as the base was developed to replace the otherwise unavoidable TBSOTf procedure. Due to the excessive steric hindrance, removal of the auxiliary was much more difficult than most literature cases. Cleavage of the oxazolidinone by reduction was almost impossible. The thiazolidinethione auxiliary was relatively easier to remove. However, several reactions reported for facile removal of thiazolidinethione auxiliaries in the literature still failed. Reductive removal of the thiazolidinethione auxiliary was most effectively realized with LiBH4 in diethyl ether in the presence of 1 equiv of MeOH (a modification of a literature procedure for removal of oxazolidinone auxiliaries in less hindered substrates). Apart from the auxiliary removal, oxidation of the alcohol into aldehyde and the deprotection of the dithiolane protecting group were also rather difficult in the present context. A range of methods were screened before final solutions were found. The five-membered ring was constructed by employing an intramolecular Mukaiyama reaction after many attempts with the intramolecular aldolization under a variety of conditions failed. The rate of elimination of the alkoxyl to form the α,β-double bond of the key intermediate cyclopentenone 49 with DBU was highly solvent dependent (very sluggish in CH2Cl2 but rather fast in MeOH). Introduction of the lower chain (which was synthesized by using a Jacobsen KHR to establish the C-15 chirality) was achieved through a Michael addition similar to the precedents in the literature. It has not been noticed before that the yield of this Michael reaction could be dramatically raised by using 3 equiv of the copper-lithium reagent 55. Reduction of the C-7 carbonyl was apparently more difficult than similar cases in the literature. After examination of many reagents under various conditions, it was found that the best reagent for yielding the α-isomer was (S)-2-methyl-CBS-borolidine/BH3 and that for the β-isomer was L-Selectride. The α- and β-isomers were then further elaborated into (+)-brefeldin A and 7-epi-BFA, respectively. An unexpected yet very interesting solubility difference between BFA and 7-epi-BFA was also observed.